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How Bret Saberhagen Inspired Bobby Bonilla's Famous Contract

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On October 27, 1985, Kansas City Royals rookie Bret Saberhagen tossed a five-hitter in Game 7 of the World Series. The Royals defeated the St. Louis Cardinals 11-0, winning the first championship in franchise history. Saberhagen won World Series MVP, and the night before, his son was born. Yes, it was a pretty memorable week.

Saberhagen, who also won the Cy Young Award, had a $150,000 salary in 1985. So how are the New York Mets — a team Saberhagen last pitched for in 1995 — paying the pitcher $250,000 per year?

The Mets are well known for their role in the famous Bobby Bonilla contract. They'll pay their former player more than a million dollars per year until he's 72 years old. But Bonilla actually has Saberhagen to thank for continuing to earn money well into retirement.

Rick Stewart/Getty Images

Back in March 1993, Saberhagen and the Mets agreed to a new contract. The deal came with $15.337 million in guaranteed money and could be worth as much as $27.75 million through 2028.

Saberhagen's deal, which made him the seventh-highest paid pitcher in the league, came with a $2.5 million signing bonus. It also featured something unusual for most contracts: deferred payments.

The Mets and Saberhagen structured the deal so Saberhagen would receive $250,000 per year for 25 years, beginning in 2004. He'll receive his last payment in 2028, 33 years after he last played for the Mets and 27 years after he retired from baseball.

Bonilla was so impressed by Saberhagen's deal that he signed a similar one the following year, in 1994. The Mets agreed to take half of the nearly $6 million they owed him in 1994 and 1995, about $3 million, and pay it in $250,000 installments over 25 years, beginning in 2003.

Somehow, that seems tame compared to Bonilla's second deferred payment with the Mets. In 1999, Bonilla was on the decline. The Mets released him, but the team still owed him $5.9 million. Instead of letting them buy him out right then, Bonilla and his agent once again showed some creativity.

The two sides agreed to a deal — the Mets wouldn't owe Bonilla money until 2011. At that point, they'd pay him $1.19 million every year for 25 years. He'll earn that last payment in 2035, a full 34 years after he retired and 36 years after his last game in a Mets uniform.

By the time both of these deals are done, Saberhagen and Bonilla will have collectively made nearly $42.5 million since they retired

Meanwhile, the Mets were excited for short-term relief in the moment. But as we see far too often with deferred contracts, they end up paying for it later on.

Read more: How Bret Saberhagen Inspired Bobby Bonilla's Famous Contract


Long Before Bobby Bonilla's 25 Year Gravy Train, This Random NFL Player Negotiated An Equally Creative And Lucrative Deal…

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If you pay attention to Celebrity Net Worth, Twitter, Facebook, the news, or everyone on ESPN, you probably heard that today is a very special day. July 1st is International Bobby Bonilla Day. On this day, 58-year-old retired MLB slugger Bobby Bonilla gets his annual $1.2 million check from the Mets (technically it's $1.4 million when you include a separate $250k annual deferment Bobby had a few years earlier).

I'm not gonna recap Bobby's deal in this article. If you really have no idea what I'm talking about, you can read this version or this version we posted years ago that originally gave Bobby's brilliant contract mass attention. The long and short of it is that in 2000, Bobby asked the Mets to defer a $5.9 million payment that was owed to him in exchange for receiving $1.2 million per year for 25 years starting in 2011. The deal essentially gives Bobby a big league contract every year until he is 72, in the year 2035.

And even though he might get all the headlines, Bobby certainly was not the first professional athlete to defer a contract. In fact, 15 years before Bobby struck his deal, an NFL player named Bill Fralic negotiated an equally interesting and unique deal when he signed with the Atlanta Falcons. Fralic's deal might not have paid as much as Bobby's, but it did have one very nice little advantage: It lasted Bill's entire life. That means Bill got paid every year through 2018, when he passed away at the age of 56.

George Rose/Getty Images

George Rose/Getty Images

Early Life

Bill Fralic was born on October 31, 1962, in Pittsburgh, Pennsylvania. He played high school football at Penn Hills High and was named to the "All Century Team" by Pennsylvania Football News. As a senior, the Pittsburgh Post-Gazette named him high school athlete of the year.

He didn't travel far for college, having won a football scholarship to the University of Pittsburgh. He played offensive tackle at Pitt and landed on the All-American squad in his junior and senior years.

NFL

Bill entered the 1985 NFL draft and was selected with the second overall pick by the Atlanta Falcons. At the time, Warren Moon was the highest-paid person in the NFL, earning $1.1 million per year. The highest-paid Offensive Lineman back then was Dean Steinkuhler, who made $650k per year. Bill's rookie deal paid $600k right out of the gate. When you include his signing bonus, Fralic would go on to earn $7 million in his first four years in the NFL. All in, he actually earned more during those first years than the #1 pick of the 1985 draft, Bruce Smith.

Perpetual Contract

So what does this have to do with Bobby Bonilla? Well, just like Bobby, Bill was concerned about his life after sports. So when it came time to negotiate his very first deal with the Falcons, he hired an expert tax lawyer. This lawyer asked the Falcons for a highly unusual provision. In addition to paying a signing bonus and offering a big contract, Bill's lawyer demanded that the Falcons pay him $150,000. Not a one-time fee of $150,000. Not $150k for the length of the contract. Not even $150k for 25 years, like Bonilla got with the Mets.

Bill Fralic requested that the Falcons give him $150,000 per year, every year for the rest of his life!

Bill went on to play nine seasons in the NFL from 1985 – 1993, during which time he went to the Pro Bowl four times. In 1992, he was one of the first NFL players to take advantage of the newly created free agency system, and by doing so, he doubled his salary from $800k to $1.6 million when he jumped from the Falcons to the Detroit Lions.

Later Career

After football, he wrestled in the WWF and was famously part of the 20-man battle royal at WrestleMania 2. He was a Falcons TV commentator from 1995 – 1997, then a Pittsburgh Panthers broadcaster from 2004-2010. He was also an early vocal opponent of steroid use in the NFL. In 1989, he even testified before Joe Biden (a Senator at the time) at a US Senate subcommittee meeting on steroid use in professional sports.

Bill spent his final years running an insurance company called Bill Fralic Insurance Services, a business he actually launched while he was still a player in the 80s.

Unfortunately, Bill died on December 13, 2018, at the age of 56 after a battle with cancer. He was just one month shy of receiving another $150k.

Read more: Long Before Bobby Bonilla's 25 Year Gravy Train, This Random NFL Player Negotiated An Equally Creative And Lucrative Deal…

Was Bobby Bonilla's Contract Financially Brilliant Or Horrendously Stupid?

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Happy Fiscal New Year! Most corporations begin their fiscal year on the first day of July. It's a chance for firms to start anew. For the New York Mets, it is the same old problem. On July 1, they immediately lose a million and a half bucks. Why? Because July 1st is Bobby Bonilla Day.

As you've probably seen all over the news and the web and right here on CelebrityNetWorth, today the Mets will send a check totalling $1.4 million to Bobby Bonilla.

The deferred payment plan was created in 1999 after the team bought out Bonilla's contract, which had one year and $5.9 million remaining.

Matthew Stockman /Allsport

Matthew Stockman /Allsport

While most lament the Mets for making a horrible business decision, it's fair to argue that both sides left money on the table.

Finance people always talk about the time value of money. Is it better to take the money now or wait and get money in installments? If you think you can wisely invest, it's usually smarter to take the money when you can and let compound interest do its thing.

Instead of paying Bonilla $5.9 million to go away, the team will pay Bonilla $29.8 million through 2035. On the surface, this looks like a $24 million blunder. But let's assume the Mets took that $5.9 million, invested it, and received a 10% rate of return.

  • In 2017, that $5.9 million would have been worth $27.1 million. That's almost enough to pay Bonilla's annuity.
  • In 2021, they would have $43 million. The Mets win.
  • In 2035, when this Bonilla saga finally ends, the potential ROI is more than $180 million. The Mets win even more.

None of this takes inflation into account, and a major change in markets could make all of these numbers moot. It also assumes a 10% rate of return, which would be difficult to achieve year after year.

The point is, there was some financial reasoning behind waiting to pay Bonilla, especially since they had been making way more than 10% per year investing with Bernie Madoff. Unfortunately, as we all know, Madoff was a fraud, and the math that made the Bonilla deal work quickly crumbled.

It should be noted that the Mets certainly did NOT end up earning a 10% return between 2000 and today. As we have covered in this article, team owner Fred Wilpon was heavily invested with Bernie Madoff. Prior to Madoff's 2008 collapse, his fund was returning a consistent (and completely fake) double-digit rate of return every year. With those returns in mind, Wilpon thought that the Mets would actually make a huge profit by deferring Bonilla's money.

Unfortunately, as we all know now, Bernie Madoff's investment fund was actually a gigantic Ponzi scheme. Wilpon, who was under the false impression that he had made $300 million investing with Madoff, had potentially lost as much as $700 million, therefore completely wiping out the perceived gains on Bobby's money.

So today it looks like the Mets lost big time. And while Bobby Bonilla is probably having a huge party knowing that there's something called Bobby Bonilla Day trending on social media, he may have lost as well!

Keep in mind, Bonilla was owed that $5.9 million. If Bobby had taken the money that he was owed at the time, invested, and hoped for a 10% return, he would easily have put away more than $100 million by 2035, instead of the $29 million he will receive. Even if he invested the entire total upfront and received a 10% return, it wouldn't be as much as taking the lump sum and investing it through 2035.

FYI: Had Bobby Bonilla taken $5.9 million in 2001 when Amazon was trading at $10 a share, and dumped it ALL into that stock… today he'd be a billionaire 🙂 And don't even get me started on what he'd be worth today if he had invested the money in Bitcoin.

Are there variables? Of course. There are no guaranteed market returns. Would Bobby have actually gotten 10% every year for decades? Probably not. There is also security in knowing a payment comes in every Fiscal New Year's Day. There is value in time, which can often trump the value of a dollar. It's something to think about every Fiscal New Year, and even Bobby Bonilla Day, too.

Read more: Was Bobby Bonilla's Contract Financially Brilliant Or Horrendously Stupid?

How Bobby Bonilla Landed The Luckiest Baseball Contract Ever

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Bobby Bonilla hasn't swung a baseball bat professionally in over a decade, yet every year on July 1st, the Mets cut him a check for $1.4 million. How is that possible? During his 14 MLB seasons, Bonilla was a six-time All-Star, a three-time Silver Slugger, and a member of the 1997 World Series champion Florida Marlins. At his peak, he could be expected to hit 20 home runs a year with 100 RBIs and a batting average well over .300. In 1991, Bobby signed a five-year $29 million contract with the Mets that made him the highest-paid baseball player ever, up to that point. Unfortunately, towards the end of his career, Bobby became somewhat of a disappointment. In 1999, with one year left on his contract, he averaged just .160 with four home runs and 18 RBIs. So why on earth did the Mets management agree to give him an incredibly lucrative new contract that still pays him millions every year today? The answer involves brilliant financial planning, an overly aggressive Mets organization, and, believe it or not, Bernie Madoff.

Bobby Bonilla bounced around a bit in the twilight of his career. A year after winning a World Series with the Marlins, he was shipped off to the Dodgers for a season. He was then brought back to the Mets, where he spent that horribly bad 1999 season, mostly arguing with manager Bobby Valentine. That season ended with an embarrassing incident when Bobby and teammate Rickey Henderson were caught playing cards in the dugout while their team lost the final game of the NLCS to Atlanta. Needless to say, there wasn't much love between Bonilla and the Mets organization in 2000. Unfortunately, the Mets still owed him $5.9 million.

Bobby knew that these were likely the very last dollars he would ever see from a big league contract. He had a maximum of three subpar seasons left in his legs. Whatever money he had saved up, plus this final payment from the Mets, would potentially need to last 40+ years. Adding to the 36-year-old slugger's anxiety was the fact that many of his fellow athletes had gone broke a few years after retiring. Athletes going broke is an unfortunately common story. A recent Sports Illustrated report found that 70% of NFL players, 60% of NBA and a high majority of MLB players are bankrupt within 2-4 years of retirement. Most of these athletes lack higher levels of education and do not have any skills that can be translated easily into the real world. Athletes are notoriously bad at managing their own money. They make terrible investment decisions and spend wildly even when there is no more money coming in. Curt Schilling lost every cent of the $50 million he made playing baseball on a failed video game company. Allen Iverson squandered a $150 million fortune on gambling, houses, jewelry, child support, and a 50-person entourage. Mike Tyson blew through a $300 million fortune. Evander Holyfield blew through a $250 million fortune. The list is endless.

Similar to professional athletes, a high percentage of lottery winners go flat broke within a few years of receiving a huge lump sum of money. Lottery winners face many of the same issues as athletes. With zero experience, most overspend and get caught up in bad investment schemes. When you win the lottery, you are given two choices typically: You can accept a smaller lump sum immediately, or you can be paid the full amount in monthly increments over many years. If you talk to any investment advisor or financial professional, 100% will recommend taking the lump sum. Even though you are accepting a lower amount, the time value of money makes it far more valuable than getting paid spread out over the years. A $60 million lump sum should, in theory, grow to be far more than the $100 million that would be eventually paid out over 30 years. $60 million today can be invested in stocks, CDs, bonds, treasury certificates, real estate etc… Regardless of what every financial advisor in the world recommends, the reality is that the vast majority of professional athletes and prospective lottery winners would be way better off spreading their money out instead of taking a lump sum.

Getty Images

When it came time to negotiate with the Mets, Bobby Bonilla was smart enough to secure one of the most forward-thinking contracts in sports history. He knew the Mets wanted him gone, but technically owed him $5.9 million. He also knew he had a young son and daughter who would be looking to go to college, and as a 36-year-old, he likely had many years worth of life to live. So at this point, Bobby and his agents offered a unique compromise: The Mets would release Bobby to play for another team, and they would delay the $5.9 million payment for 11 years, with interest. In essence, the Mets agreed to pay Bobby a total of $29.8 million (instead of $5.9 million) in 25 annual installments of $1.192 million, starting in the year 2011. When he received his first $1.192 payment, Bobby was 48 years old and had not played in the big leagues for 10 years. He has basically guaranteed himself a big league salary every year for the rest of his life. Today, Bobby Bonilla makes more per year from the Mets than most of the team's active players! So why would the Mets agree to this deal?

The Bernie Madoff Connection

In 1986, Real estate developer Fred Wilpon purchased 50% of the New York Mets for an undisclosed sum. He purchased the remaining 50% for $135 million in 2002. Wilpon was also one of the biggest investors in Bernie Madoff's Ponzi scheme hedge fund. Prior to the fund's December 2008 collapse, Madoff was returning a consistent (and completely fake) double-digit rate of return every year. With those returns in mind, Wilpon knew that the Mets would actually make a huge profit by deferring Bonilla's $5.9 million. Even though that meant agreeing to pay him more than five times the amount they owed ($29.8 million), Wilpon could safely estimate that the Mets would make $60-70 million off $5.9 million over those 25 years investing with Madoff.

Unfortunately, as we all know now, Bernie Madoff's investment fund was actually a gigantic Ponzi scheme that wiped out between $20 and $65 billion in wealth for thousands of investors. Wilpon, who was under the false impression that he had made $300 million investing with Madoff, had potentially lost as much as $700 million. Not only did this completely invalidate the justification for Bobby Bonilla's contract, but it almost forced Wilpon to sell the Mets to cover his debts. In 2011, Wilpon nearly sold 50% of the Mets to a billionaire hedge fund manager named David Einhorn, but was eventually saved by loans from Major League Baseball and Bank of America. Bobby Bonilla, meanwhile, is living the good life. On July 1st, 2013, he received his third direct deposit from The Mets for $1,193,248.20. Just five months earlier, Bobby celebrated his 50th birthday. Today, Bobby is 603 years old. He is a living lesson for why we might all be better off turning down lump sums and instead opting for deferred payments. I hope we all have to make that choice someday!

Read more: How Bobby Bonilla Landed The Luckiest Baseball Contract Ever

Happy Bobby Bonilla Day! The NY Mets Just Paid 62-Year-Old Bobby Bonilla $1.4 Million

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It's July 1st! If you're in Rwanda, you might be celebrating your country's independence from Belgium. If you're in Hong Kong, you might be marking the 21st anniversary of when the British ceded control of the city to China. If you're Liv Tyler, Missy Elliot, or Dan Aykroyd, happy birthday!

And if you're Bobby Bonilla, congratulations! You're $1.4 million richer thanks to a contract you signed two decades ago.

If you have no idea what we are talking about, today is Bobby Bonilla Day. Thanks to what has been described as "the greatest contract in sports history," today is the day that the Mets are contractually obligated to send $1,193,248.20 to Bobby Bonilla, a man who retired from professional baseball over 15 years ago. And, actually, his payment is more like $1.4 million for reasons we'll describe in a moment…

(Photo by Ronald C. Modra/Getty Images)

We've covered this story a bunch over the years, so I don't want to reiterate all the details here. If you are interested in the long version, please read this article:

"How Bobby Bonilla Negotiated The Smartest Contract In Baseball History"

The long story, short, is that back in 1999, the Mets were fed up with Bobby and wanted him off the team. The only problem was that they still owed him $5.9 million. They could have simply paid him that money and been done with it, but Bobby came to team owner Fred Wilpon with a proposal. A proposal that would turn out to be brilliant… for Bobby.

Wanting to avoid becoming one of those cliché athletes who go broke in retirement, Bobby offered to defer his $5.9 million for 11 years… until 2011. At which point, the Mets would pay him $29.8 million in 25 annual installments—one installment per year through the year 2035.

The Mets also would agree to release Bobby from his current deal, which allowed him to play two more seasons in the MLB, earning another $200k from the Braves and $900k from the Cardinals.

Team owner Wilpon jumped at the offer because he happened to be one of Bernie Madoff's biggest investors. Wilpon calculated that if he simply invested that $5.9 million with Madoff, by the time 2035 rolled around, it would have grown to around $70 million. Way more than the $29.8 million Bobby was asking for.

It was an easy yes from both parties. Unfortunately for Wilpon, Madoff was a fraud. The $300 million he THOUGHT he had earned investing with Madoff over the years didn't exist, and he actually may have LOST around $700 million.

Oh! Remember at the beginning of the article when we said Bobby's payment today is closer to $1.4 million? That's because a few years before negotiating his famous contract, he deferred half of a $6 million contract. So from 2003 to 2028, Bobby also gets an additional $250k from the Mets every year!

Way to go, Bobby!

Read more: Happy Bobby Bonilla Day! The NY Mets Just Paid 62-Year-Old Bobby Bonilla $1.4 Million

Forget "Bobby Bonilla Day", July 1st Should Really Be "Max Scherzer Day" Based On The Ridiculous Deferred Check He Cashes Every Year

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At Celebrity Net Worth, we're big fans of Bobby Bonilla Day. If you are somehow unfamiliar with Bobby's story, here's a quick primer: Bobby Bonilla is a former baseball player who retired from the major leagues in 2001. Two years before that, he was playing with the New York Mets. Then-Mets owner Fred Wilpon wanted to invest the money remaining on Bobby Bonilla's contract with Bernie Madoff (before Madoff was revealed as a fraud, of course).

Wilpon and Bonilla struck a deal. Bobby's remaining $5.9 million contract would be deferred for 11 years, at which point Wilpon would pay back Bonilla the $5.9 million plus interest in equal 25-year installments. As a result, every July 1 from 2011 to 2035, Bonilla earns $1.19 million. And actually, thanks to a second deferred contract (half of another $6 million deal), Bonilla has been getting an extra $250,000 every year since 2003 and will continue to do so until that deal runs out in 2028.

All told, Bobby earns about $1.44 million every July 1st. Not bad for a guy who hasn't swung a bat in over two decades.

But as wild and headline-worthy as Bonilla's deal is, there's a major caveat. Really, July 1st should be renamed… Max Scherzer Day.

Sarah Stier/Getty Images

Max Scherzer's Jackpot

Max Scherzer entered the league in 2008 and built a Hall of Fame-caliber career, with multiple Cy Young Awards and a reputation as one of the most dominant pitchers of his generation. But he may be equally legendary for the way he structured one specific contract.

In 2015, Scherzer signed a 7-year, $210 million deal with the Washington Nationals. The first four years of the deal were paid normally, totaling about $105 million pre-tax. The final $105 million? That's where things got creative.

Rather than take that second half of the contract during his playing years, Scherzer agreed to defer it, collecting $15 million every July 1st from 2022 through 2028.

That means each July 1st, long after he left the Nationals, Max Scherzer is handed a $15 million check just for existing.

As of July 1, 2025, Scherzer has received four of the seven payments. That's $60 million in deferred cash already banked… with $45 million still to go.

And that's not even the whole picture.

Still Pitching, Still Getting Paid

Despite entering the "retirement money" phase of his Nationals contract, Scherzer isn't actually retired. He's still in the league—and still getting paid.

After a stint with the Dodgers in 2021 and a huge contract with the Mets in 2022 (three years, $130 million), Scherzer was traded to the Texas Rangers, where he continued to earn $43 million per year.

In 2025, he's pitching for the Toronto Blue Jays, collecting $15.5 million in salary, on top of the $15 million he receives from the Nationals.

So on July 1, 2025, Scherzer is pulling in $30.5 million in total salary, with half of it hitting his bank account in one glorious, effortless lump sum.

Scherzer's deferred deal is arguably one of the most lucrative and strategically genius contracts in the history of baseball. He gets generational money spread out during the back half of his career and into retirement, locking in tens of millions in predictable, low-risk income.

It's the kind of financial arrangement that players dream of, agents obsess over, and teams only offer to someone they view as a cornerstone.

So while Bobby Bonilla Day will always hold a special place in baseball lore, let's call it like it is:

July 1st belongs to Max Scherzer.

Read more: Forget "Bobby Bonilla Day", July 1st Should Really Be "Max Scherzer Day" Based On The Ridiculous Deferred Check He Cashes Every Year

Was Bobby Bonilla's Deferred Contract Actually Smart? What If He Bought the S&P 500.. Or Apple… Or Microsoft… Or NVIDIA… Or Bitcoin :)

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Every July 1, sports fans, media outlets, and even celebrity financial websites like… ahem… us… celebrate what has become an unofficial holiday: Bobby Bonilla Day. It's the day the retired MLB outfielder receives his now-famous $1.19 million check from the New York Mets—something he's been collecting annually since 2011 and will continue to receive through 2035 (and for reasons we don't need to get into here, it's actually $1.4 million per year for the next few years). When it's all said and done, Bobby will have been paid $30 million for a 1999 contract buyout that was originally worth just $5.9 million.

The narrative is irresistible: here's a guy who hasn't played professional baseball in over two decades, still getting paid more than many active players. It's portrayed as the ultimate example of financial savvy, patience, and foresight.

And yes, on the surface, trading $5.9 million for $30 million seems like a genius move. So, every July 1, the whole world heaps praise on Bonilla for what some even call "the greatest contract in sports history." He's a passive income king. A man who outsmarted one of baseball's most storied franchises. But… did he really?

What if, instead of deferring that $5.9 million, Bonilla had just taken the money, paid his taxes, and put the remaining $3 million into an S&P 500 index fund? How would that have turned out?

Or what if he had the luck, guts, and foresight to dump it all into Microsoft? Or Apple? Or NVIDIA, or Amazon (both of which went public in 1999)… Or Google (which went pubic a few years later in 2004).

Ok and ya. Because we have to… What if Bobby had kept his money frozen in a savings account for a decade, then dumped it all into Bitcoin 🙂

Let's run the numbers and see what Bobby really gave up.

(Photo by Thomas Simonetti for The Washington Post via Getty Images)

The S&P 500: Not as Impressive as It Sounds

Suppose Bonilla had taken his $5.9 million buyout in 2000, paid taxes, and walked away with a clean $3 million. Then, like a disciplined investor, he simply dumped the money into a low-cost S&P 500 index fund and never touched it. No fancy strategies. No rebalancing. Just set it and forget it. I'll admit, I assumed this was going to be a no-brainer, better investment. I was wrong.

By mid-2025, that investment would be worth approximately $11.3 million.

And while that is a nearly fourfold return over 25 years, it's also significantly less than the $29.8 million he's set to receive from the Mets under his deferred contract.

So if we're comparing just raw financial outcomes, the S&P strategy loses. So what if Bobby had taken the lump sum, paid his taxes, and YOLO'd into some other investments…

The Tech Stock Home Runs He Missed

While the S&P 500 would've only netted Bonilla around $11.3 million, even a modest bet on the right tech company would have left that number in the dust.

Let's say instead of indexing, Bonilla put his $3 million into individual stocks. Not some obscure penny stock, but blue-chip names that were already well-known players in 2000.

Here's what that $3 million would be worth today if he had gone all-in on just one of the following companies:

  • Microsoft (MSFT): $37 million
  • Amazon (AMZN): $110 million
  • Alphabet/Google (GOOGL): $262 million (IPO'd in 2004)
  • NVIDIA (NVDA): $310 million
  • Apple (AAPL): $789 million

Bitcoin… What If…

Let's acknowledge the obvious up front: Bitcoin didn't exist in 2000. It was invented in 2008 and first began trading in 2010 at a price of just a few cents per coin. So no, Bobby Bonilla couldn't have realistically invested his deferred Mets payout in Bitcoin at the time of the deal.

But let's entertain the thought experiment anyway, because it illustrates just how much financial upside Bonilla forfeited by locking his capital into a fixed payout.

Had Bonilla invested his $3 million in Bitcoin in 2010 at an average price of $0.08, he would have acquired 37.5 million bitcoins. At Bitcoin's current price of $106,010, that stake would now be worth a staggering $3.98 billion.

Even if he had waited until 2011 and bought in at $1 per coin—considered expensive at the time—his investment would still be worth $318 million today.

Obviously, this scenario is extreme. No one expects a retired baseball player to have been an early adopter of a brand-new digital currency. But that's not the point. The point is: Bonilla didn't just defer income—he deferred opportunity. He traded control and optionality for guaranteed installments, and in doing so, missed out on every transformative investment window of the 21st century.

Read more: Was Bobby Bonilla's Deferred Contract Actually Smart? What If He Bought the S&P 500.. Or Apple… Or Microsoft… Or NVIDIA… Or Bitcoin :)

In 2007, American Apparel Founder Dov Charney Was Worth $700 Million. Then It All Came Crashing Down.

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There was a time in the early to mid-2000s when Dov Charney was sitting on top of the world. The company he founded, American Apparel, had managed to do the unthinkable: turn a made-in-USA, sweatshop-free t-shirt company into one of the hottest fashion brands on the planet. His stores were multiplying like Starbucks. His ads were on every billboard. And Wall Street couldn't get enough. American Apparel went public in 2007. Charney owned 27% of the company. That stake was soon worth over $700 million. He confidently told reporters he was on track to become Los Angeles's newest billionaire.

But behind the scenes, the man who had built his company on ethics and authenticity was fighting off a very different reputation. Stories of workplace chaos, sexual harassment lawsuits, and erratic behavior began to emerge. Former employees accused Charney of everything from walking around the office in his underwear to openly masturbating during interviews. He denied the allegations, but the damage was done.

Within a few years, he was fired, nearly broke, and eventually staring down a personal bankruptcy filing. It's one of the most spectacular self-implosions in modern retail history. So what happened?

American Apparel founder Dov Charney. (Photo by Steve Eichner/WWD/Penske Media via Getty Images)

The Rise of an Unlikely Fashion Mogul

Dov Charney was not your typical CEO. Born in Montreal in 1969 to an architect father and artist mother, Charney grew up surrounded by creative energy and ambition. His step-sister, Shira Lazar, would later become a moderately notable tech journalist.

He dropped out of Tufts University in the early '90s to pursue a niche passion: t-shirts. What began as a small wholesale business run out of South Carolina eventually moved to Los Angeles, where Charney immersed himself in the city's garment district and laid the foundation for what would become American Apparel.

His early vision was radical for the fashion world: manufacture everything in the United States, pay workers fair wages, and embrace simplicity over fast-changing trends. But Charney wasn't just selling basics—he was building a brand around a lifestyle. When the first American Apparel retail store opened in Echo Park in 2003, it didn't look like anything else in the mall. There were no logos. The lighting was harsh. The clothes were tight, unisex, and unapologetically plain. But they were everywhere. And they were cool.

By 2005, the company was pulling in over $250 million in annual revenue and expanding at breakneck speed. The company's downtown L.A. factory employed thousands and churned out over a million garments a week. Charney paid workers well above the industry average and took pride in being sweatshop-free. He positioned himself as a new kind of capitalist—one who cared about workers, who ran his company on values, and who wasn't afraid to break rules.

The IPO

In December 2007, American Apparel went public through a reverse merger with a SPAC called Endeavor Acquisition Corp. It was an unconventional move that perfectly fit Charney's unorthodox style. Overnight, American Apparel became a publicly traded company, and Dov Charney became—at least on paper—an extraordinarily wealthy man.

At the time of the IPO, Charney owned 47.2 million shares, representing a 27% stake in the company. On the first day of trading, those shares were worth around $450 million. But that was just the beginning. Within a few months, investor enthusiasm sent the stock soaring. By mid-December 2007, shares of American Apparel hit an all-time high of $15.50, pushing the company's market cap to approximately $2.7 billion.

At that price, Charney's stake was worth a staggering $730 million. He had turned a dorm-room t-shirt hustle into a billion-dollar fashion empire. The Los Angeles Business Journal quoted him saying he was "going to be one of the billionaires in Los Angeles one day."

For a brief moment, that didn't seem far-fetched. American Apparel was everywhere—at its peak, the company had over 280 stores in 20 countries, employed thousands, and had become synonymous with edgy, ethically made basics.

Shockingly, or perhaps because he truly believed in his company that much, Charney never sold a share. Not a single significant block of stock. He believed the best was yet to come. He believed he was the brand. And that belief—rooted in ego, idealism, or some volatile mix of both—would ultimately be his downfall.

The Cracks Begin to Show

Even as American Apparel's stock soared, the company's foundation was already beginning to wobble. Behind the scenes, Charney was running an empire that, according to former employees, operated more like a chaotic art project than a public company. Lawsuits began piling up. Allegations of sexual harassment, discrimination, and hostile workplace behavior became recurring headlines. One former employee alleged she was held as a "sex slave." A Jane magazine reporter claimed Charney masturbated during their interview. Another lawsuit accused him of openly snorting cocaine in the office. He denied many of the accusations, and several cases were dismissed or settled privately, but the narrative was set.

In response to mounting legal costs and public scrutiny, the company began requiring employees to sign acknowledgments that they were entering a "sexually charged" work environment. That only further fueled the fire. Investors grew nervous. Meanwhile, a 2009 immigration audit forced the company to lay off more than 1,500 factory workers—many of them undocumented. The loss of its experienced workforce led to production delays that crippled inventory and order fulfillment.

In 2013, the company made a $15 million bet on a new automated distribution center in La Mirada, California. It was supposed to modernize operations and save millions. Instead, it became a logistical nightmare. Orders were lost. Customer service collapsed. Charney, in a performative show of commitment, moved into the warehouse with a hot plate and a mattress. Rather than being seen as heroic, the stunt was perceived by board members as a sign that he was losing control of the business and himself.

By mid-2014, American Apparel's stock had cratered to under $1. Charney's $730 million stake was now worth less than $20 million. And the board had seen enough.

The Board Revolt

On June 18, 2014, Dov Charney was called into a meeting with American Apparel's board of directors. They delivered a blunt ultimatum: resign voluntarily and walk away with a multi-million dollar severance package and a four-year consulting deal, or be fired for cause. The board cited a long list of allegations, including misuse of corporate funds, violations of sexual harassment policies, and behavior that exposed the company to ongoing legal risk. Charney refused to go quietly.

The following day, he was suspended from the company he founded. Security guards were posted at the downtown L.A. headquarters to prevent him from entering. Keycards were deactivated. Surveillance cameras were installed. He was still legally CEO during a 30-day waiting period, but his days were numbered. In December 2014, the termination was made official.

Charney didn't give up. In a desperate attempt to regain control, he made a deal with hedge fund Standard General, which had been quietly acquiring American Apparel shares. Charney handed over control of his 47.2 million shares—essentially giving them the keys to his remaining power—in exchange for a $20 million loan to help him mount a proxy battle against the board. But the plan backfired spectacularly. Standard General used their leverage to install new board members who had no intention of reinstating Charney. His fate was sealed.

He responded with a flurry of lawsuits. He sued American Apparel for defamation, filed complaints against Standard General, and accused board members of conspiring to push him out. But the legal salvos went nowhere. His defamation case was tossed. His buyback bid was rejected. And by late 2015, American Apparel filed for bankruptcy, wiping out what little remained of his ownership.

Charney had once claimed he'd be a billionaire. Now, he was broke, representing himself in court, and sleeping on a friend's couch on the Lower East Side.

Reinvention, Bankruptcy, and a Netflix Reckoning

After losing American Apparel, Charney didn't disappear—he regrouped. In 2016, he launched a new venture: Los Angeles Apparel, a wholesale basics brand built in the image of its predecessor. The pitch was familiar: ethically made, sweatshop-free clothing manufactured in a vertically integrated factory in South Central L.A. Many of his former employees returned. So did the aesthetic—unbranded t-shirts, lo-fi photography, provocative ad campaigns, and Charney's unmistakable creative fingerprints.

For a while, it looked like the comeback might stick. By 2017, the factory had more than 350 workers. Kanye West's Yeezy brand reportedly sourced blanks from Los Angeles Apparel. During the early days of the COVID-19 pandemic, Charney pivoted to making face masks and medical gowns. But disaster struck again. In June 2020, a coronavirus outbreak at the factory infected over 300 workers and killed four. The Los Angeles Department of Public Health ordered the plant shut down for violating safety protocols.

Two years later, in 2022, Charney filed for personal bankruptcy. He reportedly owed up to $50 million—much of it stemming from the failed Standard General proxy battle—and claimed minimal remaining assets. Even his new side project, Arya's Vintage Closet, filed for bankruptcy protection. For the man who once ran a $2.7 billion fashion empire, it was a staggering fall.

Yet somehow, Charney is still standing. Los Angeles Apparel continues to operate, and in 2025, he announced plans to open a new retail store in New York City. He's publicly distanced himself from Kanye West after West's antisemitic statements, but hasn't entirely faded from the culture he helped shape.

Today, Netflix released "Trainwreck: The Cult of American Apparel," a documentary chronicling the brand's meteoric rise, scandal-filled downfall, and Charney's complicated legacy. The film doesn't just examine the company—it reexamines the man behind it: a self-described "Yiddish hustler" whose empire was built on idealism, disruption, sex appeal, and chaos. Whether Charney was a visionary or a cautionary tale depends on who you ask. But one thing's undeniable: he changed fashion. And then, he lost everything.

Read more: In 2007, American Apparel Founder Dov Charney Was Worth $700 Million. Then It All Came Crashing Down.


Drake Lowers Asking Price Of 20-Acre, $24,000 Square Foot Beverly Hills Mansion

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In March 2022, Drake made one of the biggest celebrity real estate purchases in recent memory, shelling out $75 million to acquire a lavish 20-acre compound in Beverly Hills from British singer Robbie Williams.

The property was never publicly listed, but insiders reported that the off-market deal closed in the mid-$70 million range, and records later confirmed the exact price. The seller, Williams, had purchased the estate in 2015 for $32.7 million from Guess? jeans co-founder Armand Marciano, who built the mansion from the ground up in 2001.

The estate sits at the end of a long private driveway and offers more than 24,000 square feet of living space, including 10 bedrooms and 22 bathrooms. Its features include a hidden tennis court, massive mosaic-tiled swimming pool and pool house, 11-car garage, wine cellar, gym, screening room, game room, and three separate ensuite staff bedrooms with their own kitchen. The property also boasts sweeping city, canyon, and ocean views across its manicured gardens and steep hillsides.

At the time of the purchase, Drake had recently inked a massive $300–$400 million overall deal with Universal Music Group, pushing his net worth to a quarter-billion dollars.

For whatever reason, Drake developed a bit of buyer's remorse. In May 2023, Drake listed the mansion for $88 million, seeking a potential $13 million flip. It was a bold move given the worsening economic climate: interest rates had doubled, luxury buyers were vanishing from California, and the newly enacted Los Angeles "mansion tax" meant a 5.5% surcharge — or $4.8 million — on any sale over $10 million.

As months passed without a buyer, speculation grew that the sale was being driven less by financial motives and more by reputational fallout. In 2024, Drake's very public feud with Kendrick Lamar reached a boiling point, and the general consensus declared Kendrick the winner. With Lamar being an L.A. native, some speculated that Drake's sudden eagerness to unload the Beverly Hills property was due, at least in part, to the optics of sticking around.

When no buyer emerged, Drake switched tactics: he listed the estate for rent at $250,000 per month. Still no takers.

And now, the asking price has officially been cut to $79 million — a far more modest $4 million gain above what he paid. Still a tough sell in a sluggish ultra-luxury market, especially once taxes, transaction fees, and years of upkeep are factored in.

Regardless of what happens with the property, Drake's real estate portfolio remains elite. In Toronto's Bridle Path neighborhood, he owns a 50,000-square-foot custom-built mansion with a 3,200-square-foot master bedroom, a regulation-size indoor basketball court, and a pyramid-shaped skylight above center court. And in 2023, he dropped $15 million to acquire a 300+ acre luxury ranch resort in Brenham, Texas.

But for now, his dream compound in Beverly Hills remains on the market — and the clock is ticking.

Read more: Drake Lowers Asking Price Of 20-Acre, $24,000 Square Foot Beverly Hills Mansion

The Largest Average Annual Salaries In Sports Contract History

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When we published our ranking of the largest sports contracts of all time, it was filled with eye-popping numbers: Juan Soto's $765 million deal with the New York Mets. Shohei Ohtani's $700 million contract with the Los Angeles Dodgers. Lionel Messi's $674 million leaked agreement with FC Barcelona. These were the biggest deals ever signed by professional athletes, ranked purely by total contract value.

That list, now featuring more than 40 contracts over $250 million, is dominated by Major League Baseball players, with a few huge outliers from global soccer, the NBA, and NFL quarterbacks. Soto's contract runs for 15 years. Ohtani's for 10. Patrick Mahomes famously signed a 10-year, $503 million deal. The common thread: length. These massive totals are usually built on long-term commitments that stretch across a decade or more.

But here's where things get interesting: none of those record-setting deals ranks as the highest in terms of average annual salary. In fact, the biggest paydays per year often come from much shorter-term contracts, especially in sports like soccer and basketball, where player movement is frequent and top-tier talent commands extreme premiums.

That's what this list is all about: the largest sports contracts of all time based on how much an athlete earns each year, not over a decade or more.

For example, Shai Gilgeous-Alexander just signed a 4-year, $285 million supermax extension. In terms of the largest contracts of all time, that deal would land at #25. But in terms of average annual salary, it's one of the biggest in history. It is the #1 biggest in NBA, MLB and NFL history.

(Photo by Tayfun Coskun /Anadolu via Getty Images)

Top 10 Largest Sports Contracts by Average Annual Earnings

Rank Athlete Contract Average Annual Salary
1 Cristiano Ronaldo (2025) 2 years, $620 million (Al Nassr) $310 million
2 Karin Benzema (2023) 2 years, $436 million (Al-Ittihad) $218 million
3 Cristiano Ronaldo (2022) 2.5 years, $536 million (Al Nassr) $214.5 million
4 Lionel Messi (2017–2021) 4 years, $674 million (FC Barcelona) $168.5 million
5 Kylian Mbappé (2022) 3 years, $681 million (PSG) $227 million*
6 Shai Gilgeous-Alexander (2025) 4 years, $285 million (Thunder) $71.25 million
7 Shohei Ohtani (2023) 10 years, $700 million (Dodgers)** $70 million
8 Canelo Álvarez (2018) 5 years, $365 million (DAZN) $73 million
9 Jayson Tatum (2024) 5 years, $314 million (Celtics) $62.8 million
10 Jaylen Brown (2023) 5 years, $303.7 million (Celtics) $60.7 million

*Mbappé's figure includes a $180 million signing bonus and incentives
**Ohtani's deal is heavily deferred; only $2 million per year is paid through 2033

Sovereign Soccer Money Leads the Way

Saudi Arabia's massive push to attract global soccer talent has rewritten the record books. Cristiano Ronaldo's two separate deals with Al Nassr — first in 2022, then a richer extension in 2025 that made him a billionaire — now rank as the top two highest annual salaries in sports history. His latest contract pays $310 million per year, including salary, bonuses, and equity stakes.

Karim Benzema isn't far behind. His two-year, $436 million contract with Al-Ittihad averages $218 million per year, identical to Ronaldo's earlier deal. Kylian Mbappé, who stayed with PSG in 2022 despite interest from Real Madrid, secured a three-year pact that reportedly works out to $227 million annually, depending on bonuses and incentives.

NBA Stars Are Right There Too

In July 2025, Shai Gilgeous-Alexander signed the richest deal in NBA history in terms of annual value — a 4-year, $285 million extension that works out to $71.25 million per season. That edges out Shohei Ohtani's deferred $70 million average and puts Shai just behind some of the Saudi-backed soccer stars.

Jayson Tatum and Jaylen Brown, both with the Boston Celtics, also crack the list with supermax extensions worth more than $60 million annually. Thanks to rising salary caps and a smaller roster size, the NBA continues to generate more per-player wealth than any other American team sport.

Baseball's Numbers Look Different Here

Shohei Ohtani's $700 million deal looks massive on paper — and it is — but much of that money is deferred until 2034. While the deal technically averages $70 million per year, he's actually receiving just $2 million per year for the first 10 seasons.

Meanwhile, Juan Soto's 15-year, $765 million deal — the largest total contract in sports — only averages around $50 million per year, depending on whether his opt-out is triggered or overridden. In terms of AAV, Soto doesn't crack the top 10.

The Real Takeaway

If total contract value tells us who signed the flashiest headline, average annual earnings tell us who's actually taking home the most money each year. It's no surprise that soccer and basketball stars dominate this list, where shorter deals are paired with massive payouts and often guaranteed money.

In today's sports economy, the real financial power isn't always in the size of the contract — it's in the speed of the paycheck.

Read more: The Largest Average Annual Salaries In Sports Contract History