August 6, 2026

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Front Office Sports - Asset Class


Social media has been flooded with clips of pro athletes complaining that their multimillion-dollar contracts don’t go as far as people think. Chris Bosh tells
Front Office Sports “people should listen, because they’re telling the truth.” One wealth adviser whose clients include pro athletes says “the general public assumption—which is that if you make it to the pros you are set for life—is far from true.”

—Ben Horney

First Up

  • A new deal between the Yankees and Polymarket will see the prediction market with “rotating home plate signage” visible to fans in the ballpark and viewers watching games.
  • DraftKings has been hit recently with three lawsuits, with the plaintiffs alleging that DraftKings Predictions is nothing but an illegal sportsbook.
  • Former NFL player Jason Wright, now overseeing Ariel’s Project Level, made the case for women’s teams as a higher-growth opportunity than men’s right now. 
  • Incoming MLS commissioner Larry Berg called the opportunity to raise the league’s TV rights revenue “uncapped upside.”

Why Pro Athletes Are Saying Their Big Contracts Weren’t So Big

Steve Dykes-Imagn Images

Social media has recently been flooded with clips of pro athletes lamenting that their multimillion-dollar contracts don’t go as far as people think. While such complaints can be easy to dunk on, the underlying point is important. The problem is the messenger.

The recent wave may have started with resurfaced clips of JJ Redick, one from February 2024 and another from March 2024, explaining how taxes and other costs can dramatically reduce a player’s take-home pay. 

“I think people should listen, because they’re telling the truth,” Chris Bosh recently told Front Office Sports. “And it’s really interesting how people don’t want to listen to that, but if I told you that player X is signing a three-year, $150 million deal, you’ll believe it. It’s not $150 million. That’s what they’re trying to get people to understand.”

Financial advisers who work with athletes say the public often overestimates how wealthy professional athletes actually are, especially given taxes, short careers, and, in some cases, financial mismanagement.

“The general public assumption—which is that if you make it to the pros you are set for life—is far from true,” says Perigon Wealth Management’s head of sports and entertainment Marc Specht. 

Plus, plenty of athletes have seen fortunes evaporate after trusting the wrong advisers. Former NBA stars Tim Duncan and Toni Kukoč have both accused financial advisers of mishandling or stealing their money. 

“That’s Where Things Took a Dive”

Hall of Fame wide receiver Terrell Owens is among the highest-profile NFL examples. He made nearly $80 million in playing contracts over the course of his 16-year NFL career. Yet by 2012, two years after he played his last NFL game, almost all of his earnings were gone, in part because half of that total went to taxes, agent fees, and other costs. According to Owens, it’s also because he trusted the wrong people to manage his money.

Owens blames his former agent, Drew Rosenhaus, and the financial advisers he was connected to through Rosenhaus, for draining his bank account while he focused on football. 

“I trusted those individuals to manage my finances,” he said during the third annual FOS Huddle in the Hamptons. “That’s where things took a dive.”

Around 2010, Owens said forensic accountants he hired uncovered late payments, missing funds, and what he alleges was an unauthorized bank account opened using his power of attorney. In 2013, Owens sued Rosenhaus, but the suit was later sent to arbitration, and by 2018 he dropped his case. He said he withdrew his suit because the alleged fraud was discovered after the legal deadline to file a claim. Rosenhaus declined to comment.

Owens has since built a portfolio of investments, from a team in start-up tennis league Intennse to his Eighty-One wine brand. He credits his financial turnaround in part to the opportunities that came with becoming a Hall of Famer, but he says the most important change was becoming more involved himself. He now makes sure to find “the time to have eyes on the eyes that are on everything.”

Not every athlete will face the same issue as Owens. For many, the biggest challenge is resisting the pressure to spend big when they first start receiving paychecks.

“It’s enticing for a lot of players to have that big splash,” says Nolan Cooney, a former NFL punter who now works at Perigon. “Education is a big piece of it; players need to understand how much money they are actually going to have.”

Specht recommends that anyone planning to work with a financial adviser—not just athletes—check the FINRA BrokerCheck platform, which will show whether an adviser has a clean record.

“You just type in the person’s name,” Specht says. “Have they been sued? Fired? All you have to do is look.”

“That Education Is What We Need”

Redick was just the start of the trend. Last month, newly signed 76ers forward Jaylen Brown was featured in a viral clip talking about how “the agency model isn’t working” because so many players “go broke after they retire.” 

A CJ McCollum clip went viral in July that featured the Hawks guard talking about how a $2 million NBA salary ends up being less than $1 million after taxes and agent fees; McCollum said during the interview he was living off a $12,000 energy drink deal early in his career. 

Similar clips from Dwight Howard, Draymond Green, Odell Beckham Jr., Joe Haden, and Ndamukong Suh have circulated this summer, prompting criticism from fans and fellow athletes alike. Bucks forward Kyle Kuzma said the real issue is “lifestyle creep,” not taxes or fees, posting on social media that “it’s exhausting hearing athletes break down how their millions ‘aren’t really millions’ after taxes and fees.” Former NBA pro David West posted on social media, “Gotta cease and desist these convos man.”  

“1% of the 1% of the 1%”

The underlying point is sound, but pro athletes are the wrong messengers, according to DePaul University professor of forensic accounting Kelly Richmond Pope.

“Yes, pro athletes are talking about a legitimate gripe in the scale of the universe they live in, but that is the 1% of the 1% of the 1% of the population,” she says. 

Many people watching from the outside agree that pro athletes aren’t the right people to deliver the message. But Bosh says the backlash misses the larger point.

“That education is what we need,” he said. “It’s what people need, especially when you’re coming into this kind of money.” 

Ryan Rosegarten, a financial adviser at UBS who focuses on clients in sports and entertainment, sees all sides. He notes that “most pro-level athletes make more in a few years than the typical American makes in a lifetime.” But players with short careers and modest contracts face a different financial reality.

“At the end of the day, it comes down to decision-making,” Rosegarten tells FOS. “That goes for anyone.”

Deal Flow

Wemby-Backed Sports Drink Gets Investment

Jun 13, 2026; San Antonio, Texas, USA; San Antonio Spurs head coach Mitch Johnson talks with San Antonio Spurs forward Victor Wembanyama (1) against the New York Knicks in the second half during game five of the 2026 NBA Finals at Frost Bank Center.

Dustin Safranek-Imagn Images

  • Private equity firm Axum Capital Partners has purchased a majority stake in Victor Wembanyama–backed sports drink Barcode. Wembanyama has been an investor in Barcode since 2023; the company was cofounded in 2020 by NBA pro Kyle Kuzma; other investors include Carmelo Anthony and Jordan Clarkson.
  • J.J. Watt is investing in Texas-based energy company Base Power, which aims to provide “affordable, reliable energy to Americans.” The company currently offers services to more than 30,000 homes across Texas and Illinois. Watt’s investment is part of a $1 billion Series D funding round.
  • Yankees legend Derek Jeter is backing Alum, a new hospitality company focused on properties near college campuses that launched this week. Alum’s first development will be a 116,000-square-foot property that will include 68 luxury condo-hotels close to the University of Alabama, and the company is in active negotiations about other sites in places near schools like Ohio State and Notre Dame.
  • The $55 billion go-private sale of Electronic Arts has been completed, meaning the maker of sports video games like Madden and EA Sports College Football is now formally owned by a group featuring the Saudi PIF, Jared Kushner’s investment firm Affinity Partners, and private equity giant Silver Lake. The deal was first announced last September.
Legal Corner

Prediction-Market Madness

Kalshi logo appears in this illustration taken April 22, 2026.

REUTERS/Dado Ruvic/Illustration

  • Kalshi suffered a significant loss in a lawsuit it filed in February against the state of Utah, with a federal judge ruling the state can seek to enforce its sports betting laws against the prediction-market platform. “Prediction markets are gambling, full stop,” Utah Gov. Spencer Cox posted on social media. Kalshi is appealing to the 10th Circuit.
  • Novig has sued New York attorney general Letitia James and other state officials to prevent the same aggressive action taken last week against Kalshi (New York is seeking at least $36 billion in damages in a suit that aims to shut Kalshi down in the state). Novig, which just relaunched as a federally regulated prediction market, became the first prediction-market platform to reach a team-level deal with an MLB club last week through an agreement with the Mets.
  • Polymarket was sued in Illinois federal court by a man who claims the company incorrectly resolved a market he bet on regarding whether Israel would “invade Lebanon in September” of 2024. The plaintiff says he’s owed at least $218,336, which includes the $108,268 he bet on the market plus the amount he would have won if the market resolved to “yes.” The market was resolved to “no” on a technicality, but he claims Israel “launched a ground invasion to establish control of southern Lebanon” on Sept. 30, 2024. 

Editors’ Picks

Bryson DeChambeau’s Agency Denies Role in LIV Rescue Deal

by David Rumsey
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Tom Brady Explains His Aggressive Push Into Trading Cards

by Alex Schiffer
Brady talked to FOS about his eponymous card company.

Blazers Gain Public Backing, but Arena Talks Still Contentious

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Citizen support for the arena renovations arrived from several different sectors.
Events Video Games Shop
Written by Ben Horney
Edited by Lisa Scherzer, Catherine Chen

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