Here’s the Best Way Ever to Get Passive Income – But Good Luck Getting It for Yourself

Here’s the Best Way Ever to Get Passive Income – But Good Luck Getting It for Yourself

By Josh Katzowitz, WCI Content Director
Bobby Bonilla earned nearly $50 million during his 16-year Major League baseball career. He made seven All-Star teams, and in 1991, he signed the richest contract in baseball history—a five-year deal worth $29 million (about $67 million in today’s money). Somehow, even though he retired in 2001, Bonilla, because he was a talented ballplayer last century, is still making passive income.

At The White Coat Investor, we often talk about passive income, whether it’s through some form of real estate investing, an entrepreneurship that starts active and then becomes passive, or if you lend out money and charge interest.
But I’m not sure anything beats what Bonilla has managed to accomplish every summer in his retirement. That’s because every July 1, known colloquially throughout the sports world as Bobby Bonilla Day, the New York Mets pay Bonilla $1.2 million. They’ve been sending him checks since 2011, and they’ll continue to do so until 2035. Bonilla was 28 years old when he signed that record contract. He’s 61 years old today. He’ll be 72 when he receives the final payment from the Mets. That’s a long time to make millions.
It might be one of the silliest (or, at least, the most mocked) player contracts of all time, especially since the Mets traded him to Florida in 1997, where Bonilla helped the Marlins win a World Series (the Mets, meanwhile, have been championship-less since 1986). But for Bonilla, he’s literally been getting paid every year for the past 13 years for doing absolutely nothing, the result of a $5.9 million contract he signed before the 1999 season.
If we’re grading Bonilla on his ability to earn passive income, I’m giving him an A++.
How Bobby Bonilla Day Came to Be
He was a great player in his prime, but Bonilla spent the last four years of his career suiting up for four different teams (including the Mets again in 1999, where he signed that last $5.9 million deal). At that point, Bonilla was basically a shell of himself. How is he then still getting paid by the Mets more than two decades after he signed that second contract with New York?
Here’s how it works, as noted by CBS Sports:
“The Mets released Bonilla in January 2000 but were still on the hook for his $5.9 million salary that season. Believing they were poised to make a significant profit through their investments with Bernie Madoff, Mets ownership instead agreed to defer Bonilla’s salary with 8% interest and spread the payments across 25 years from 2011-35.”
(Yikes, when Bernie Madoff gets involved, you know things are not going to be great for any investor not named Bernie Madoff or Bobby Bonilla. But if the Mets had made a 10% return on their Madoff investments, they would have saved millions before having to pay Bonilla beginning in 2011.)
CBS Sports continues . . .
“Well, Madoff’s Ponzi scheme fell apart, and Bonilla’s $5.9 million swelled to $29.8 million from 2000-11. That $29.8 million divided by 25 years equals the annual $1.19 million payment.”
(Yes, Bonilla loses some of that payment due to inflation, but it’s hard to feel sorry for the guy, right?)
“Bonilla’s deferred salary with the Mets is the most famous July 1 payment in baseball, hands down, but it is not the only July 1 payment in the game. In fact, Bonilla has a second deferred salary agreement with the Baltimore Orioles, who still owe him $500,000 a year from 2004-28. July 1 is a good day in the Bonilla household.”

Bonilla isn’t the only one who caught a golden parachute after his professional baseball career was complete.

Ken Griffey Jr. has been paid about $3.6 million every year by the Reds since 2009 (which runs through this year).
Manny Ramirez gets about $2 million per year from the Red Sox from 2011-2026.
Chris Davis will receive $3.5 million from the Orioles until 2032. Then, he’ll be paid $1.7 million annually from 2033-2037.

But all of those figures pale in comparison to Shohei Ohtani.
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How Does Shohei Ohtani Compare to Bobby Bonilla?
In December 2023, Shohei Ohtani and the Los Angeles Dodgers agreed on a 10-year, $700 million deal that boggles the mind. Aside from the astronomical numbers, the agreement calls for Ohtani to take home just $2 million a year for the next decade, meaning he’s deferring the rest of the $680 million over a 10-year period beginning in 2034 (apparently, he’s not making any extra interest on that deferred compensation).
That means he’ll make $68 million per year from 2034-2044, so we can turn Bobby Bonilla Day into Shohei Ohtani Day without too much overlap.

Whether Ohtani’s people structured the deal that way so he can avoid having to pay huge state taxes in California or because he’s not afraid of inflation, it’s easy to see why Ohtani doesn’t mind this deal. He’ll never have to worry about buying an annuity (the Dodgers are basically providing that for him), and he reportedly makes $50 million a year from endorsements anyway.
But you could also make the argument that Bonilla is getting a better deal dollar for dollar than Ohtani.
As Elisabeth Dellinger of Fisher Investments writes,
“Bonilla made a rational financial decision banked on the power of compound growth. No market volatility to think about for the first 11 years, no 2000-2002 or 2007-2009 bear markets to navigate, just a cool, steady 8%. I did the math once, and if you presume he invests his entire gross paycheck every July 1 (in my fantasy math land there are no taxes) in the S&P 500 and compare that to a hypothetical investment of $5.9 million in January 2000, he made the right choice. Yet this is not an argument for dollar cost averaging—just a reminder that compound interest adds up big time.
Anyway, Ohtani is sort of doing the opposite. He is just getting paid for 10 years of service across the next 20 years and taking most of the cash on the back end, with no interest. So, as many have pointed out, he is actually going to lose purchasing power to inflation. Some analysis, using a 3% inflation rate, argues that once you adjust for this, the contract value is more in the neighborhood of $460 million in present dollars. Where Bonilla reaped compound interest, Ohtani is basically giving the Dodgers an interest-free loan.”

Either way, it’s a testament to Bonilla and his business team that they were thinking about the best way to earn passive income a half-century after he started his career. And he loves that he’s recognized for his financial savvy.
“People say, ‘Oh, that’s Bobby Bo. Oh my goodness. He is part of one of the greatest contracts in sports. I love what he did,’” Bonilla told Action Network in 2022. “And that kind of brings a smile to my face . . . I want to see more players—and not just in baseball, football and basketball—think about tomorrow.”
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Money Song of the Week
Jason Isbell is probably richer than he ever thought he’d be. The rock/alt-country/folk singer-songwriter is one of the more popular acts in the Americana genre (though he’s still overshadowed by singers like Chris Stapleton and Sturgill Simpson). After nine studio albums and six Grammy wins, he’s begun to dress more like a successful rock star than the jeans-and-plaid outfits he usually sported when he was a guitarist for the southern rock group, Drive-By Truckers.
Some of his fans have scoffed at the fashion selfies he’s been dropping on Instagram lately, but he’s earned his wealth (he can sell out theaters multiple nights in various cities throughout the US, a long way from when I saw him opening for regional acts in small clubs in the early 2010s).


He also hasn’t forgotten the blue-collar family who raised him. In the 2015 tune, “Something More Than Free,” Isbell tells the tale of his father, who works 6-7 days a week and is often too tired to attend church on Sundays (which is the only day he can possibly sleep past 5am).
Someday, perhaps the senior Isbell will be rewarded for all his toil. As Isbell sings,
“When I get my reward, my work will all be done/And I will sit back in my chair beside the father and the son/No more holes to fill and no more rocks to break/And no more loading boxes on the trucks for someone else’s sake.
“’Cause a hammer needs a nail/And the poor man’s up for sale/Guess I’m doin’ what I’m on this Earth to do.
“And I don’t think on why I’m here or where it hurts/I’m just lucky to have the work/And every night I dream I’m drowning in the dirt/But I thank God for the work.”

Recently, I watched a Max documentary on Isbell, and in it, he talked about the money troubles his parents experienced when he was growing up in rural Alabama.
Said Isbell: “My parents did everything they could to make my childhood a positive experience. They couldn’t do everything that they needed to do. Dad was always stressed about money. Mom was not great with money. Both had a pretty short fuse. They’d start arguing, and it was a very quick escalation with them. The house was small, and the walls were thin. The amp was loud. I couldn’t hear them if I turned it up loud and played rock ‘n roll guitar; I couldn’t hear them yelling at each other.”
Just because Isbell has made more money than his folks ever did, that doesn’t mean life isn’t hard for him. Watch that documentary called Running With Our Eyes Closed, and you’ll see the toll his career takes on his family and his own mentality. Let the man take his selfies if it makes him happy. He’s not loading boxes on trucks, but he’s earned his wealth.
Tweet of the Week
It’s good to have goals.

1972: 42-year-old Jack Lynch of Dublin attempts to drink 20 pints (about 11 litres) of Guinness beer in one sitting to enter the Guinness Book of Records!☘️👌
— PintsO’Guinness (@PintsO_Guinness) May 2, 2024


not something we monitor anymore, so don’t even think about it
— Guinness World Records (@GWR) May 2, 2024

Assuming you’re not one of the best baseball players in the world, what’s the ideal way for you to make passive income? Is there a better example than a retired ballplayer still cashing in? Comment below!
[Editor’s Note: For comments, complaints, suggestions, or plaudits, email Josh Katzowitz at [email protected].]

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