Baseball history is littered with owners who have thrown around cash like a billionaire at a blackjack table—only to end up bust.
Some did it out of desperation, others were just plain bad at evaluating talent, and a few… well, they should’ve hired better advisors. So, let’s count down 15 MLB owners who made it rain on the wrong players—and paid the price.
15. Arte Moreno (Los Angeles Angels) – Anthony Rendon, $245M
Remember when Anthony Rendon was a World Series hero in Washington? Yeah, Arte Moreno sure does. Unfortunately, the guy who showed up in Anaheim looks like he’s still on his victory parade. Between injuries and an apparent disinterest in baseball, Rendon has been more “day-to-day” than your flaky friend who can never commit to plans.
14. Mike Ilitch (Detroit Tigers) – Prince Fielder, $214M
Mike Ilitch wanted a ring so badly, he backed up the Brinks truck for Prince Fielder… who lasted two seasons in Detroit before getting shipped to Texas for Ian Kinsler. The Tigers ate a chunk of his contract while Prince ate… well, a lot of things. Injuries cut his career short, but the financial damage was already done.
13. Steve Cohen (New York Mets) – Francisco Lindor, $341M
Steve Cohen is the richest owner in MLB and loves spending big, but Francisco Lindor’s production has been more “above average” than “superstar.” Sure, he’s solid, but when you drop $341 million on a guy, you expect MVP numbers—not a shortstop hitting .250 and Mets fans crying into their Shake Shack burgers.
12. Peter Angelos (Baltimore Orioles) – Chris Davis, $161M
There’s bad contracts, and then there’s Chris Davis’ contract. Peter Angelos gave him $161 million after one monster season, and Davis responded by forgetting how to hit a baseball. His batting average dropped so low, he made pitchers look like Ted Williams in comparison.
11. John Middleton (Philadelphia Phillies) – Jake Arrieta, $75M
Jake Arrieta was an ace in Chicago. In Philly? Not so much. John Middleton cut the check, expecting dominance, but instead got a guy who looked like he was throwing batting practice. A 4.36 ERA and an attitude problem later, the Phillies were left wondering what they had paid for.
10. Tom Ricketts (Chicago Cubs) – Jason Heyward, $184M
Sure, Jason Heyward gave an inspiring rain-delay speech in Game 7 of the 2016 World Series. But unless that speech came with a free “Money Well Spent” certificate, the Cubs massively overpaid. His bat disappeared the moment he got to Chicago, and fans spent seven long years waiting for it to return.
9. Hal Steinbrenner (New York Yankees) – Jacoby Ellsbury, $153M
If Brian Cashman had a mulligan, he’d use it on Jacoby Ellsbury. Hal Steinbrenner wrote the checks, but Ellsbury barely played due to an endless list of injuries. The Yankees literally couldn’t find him for a few seasons, as if he entered the MLB’s version of the Witness Protection Program.
8. Jeffrey Loria (Miami Marlins) – Wei-Yin Chen, $80M
Loria was never one to spend big, but when he did, he made sure to set money on fire. Wei-Yin Chen was supposed to anchor Miami’s rotation, but instead, he got injured, was ineffective, and became a financial burden that lasted years. Classic Loria.
7. Mark Attanasio (Milwaukee Brewers) – Ryan Braun, $105M (Post-PEDs)
Ryan Braun was an MVP, but after getting caught for PEDs, Milwaukee still gave him a $105M extension. What could go wrong? Turns out, quite a lot. His numbers declined, injuries piled up, and suddenly, the Brewers were paying a fortune for nostalgia.
6. John Fisher (Oakland A’s) – Billy Butler, $30M
You’d think a team like the A’s would be careful with their limited funds. Nope. John Fisher gave Billy Butler $30 million, and in return, Butler gave them a designated hitter who couldn’t hit. He was released midway through the deal, but the memes will last forever.
5. Bob Castellini (Cincinnati Reds) – Homer Bailey, $105M
Nothing screams “bad contract” like paying $105 million to a pitcher with a career ERA north of 4.00. The Reds bet on Homer Bailey after a couple of no-hitters, but instead of dominance, they got a human piñata for opposing hitters.
4. Fred Wilpon (New York Mets) – Bobby Bonilla, $1.19M every July 1st
It wouldn’t be a “bad contract” list without Bobby Bonilla Day. The Wilpons deferred his contract to “save money,” but instead, they locked themselves into annual payments through 2035. Mets fans get fireworks every July 4th, but Bonilla gets his payday every July 1st.
3. Tom Hicks (Texas Rangers) – Alex Rodriguez, $252M
A-Rod was incredible in Texas, but Tom Hicks never realized one superstar can’t carry an entire franchise. The Rangers were so desperate to escape the contract that they paid the Yankees to take him. Imagine giving your friend money to take your old couch off your hands—that’s basically what happened.
2. Mike Piazza’s Investor Group (Miami Marlins) – Giancarlo Stanton, $325M
The Marlins gave Stanton a record $325 million deal, then realized, “Wait, we’re the Marlins—we don’t do this.” They traded him to the Yankees while still paying parts of his contract, because that’s just how Miami operates.
Related: Ranking All Current NFL Team Owners from Worst to Best
1. Frank McCourt (Los Angeles Dodgers) – Andruw Jones, $36M
Of all the disastrous signings in MLB history, Andruw Jones’ stint with the Dodgers might be the funniest. Frank McCourt thought he was getting a future Hall of Famer, but instead got a guy who hit .158 and looked allergic to fitness. LA fans were booing him before April was even over.
Related: 15 Shocking Sports Trades That Tore Fanbases Apart
