Last Updated: October 15th, 2026 by Matthew Brown
Contracts are such a pivotal thing in sports. Baseball has had the unique issue of no salary cap compared to the other major sports in the United States. That has allowed teams to make some terrific decisions and also some horrific decisions.
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I know that salaries can be a point of argument among fans and analysts alike. It can get people to say, "they're paying that guy how much?" With that being said, let's go over some of the most infamous contracts in baseball history.
The most overpaid players in baseball history have sparked countless arguments among fans and analysts alike.
10. Bobby Bonilla
Bonilla hasn't played baseball for a while, yet he is still being paid by the New York Mets. A six-time All-Star, Bonilla was definitely a really good player when he signed a big deal to go to Queens.
Then an eventual buyout in 2000 gave him an option of a lump sum or a deferral of payments over many years. I think we have been more familiar with deferred payments recently, thanks to the Los Angeles Dodgers. But Bonilla is probably as well known for this tactic as any player in history.
New York Mets still pay him $1.19 million every July 1six All-Star selections
9. Alex Rodriguez
Rodriguez was getting a little older as he signed a massive contract with the New York Yankees. This was one of those contracts where it didn't really matter as much to the organization for there to be a risk of dead money at the end of it.
The thing is, he had to serve a PED-related suspension by the end of it, basically ending his career and forcing the Yankees into some wasted money in a way that they didn't want.
Yankees10-year, $275 million deal
8. Albert Pujols
Pujols was a major get for the Los Angeles Angels in 2012. But the way he came into the situation was a way that probably anyone would. $240 million dollars is a ton of money, and the guaranteed nature of it made him get into such a relaxed state that he was really just a happy uncle in the dugout by the end of his career.
Injuries slowed him down a lot when he was in Southern California. The Angels probably didn't recoup enough of the massive investment they put into one player.
7. Barry Zito
As many have done over the years from Oakland, Barry Zito was a bargain who was looking to become a big investment. The San Francisco Giants were willing to make that investment in the form of $126 million dollars over seven years.
But it wasn't exactly the type of pitcher that could guarantee dominant performances throughout his career. He pitched a little bit more to contact. He wasn't exactly striking out guys left and right.
A 5.15 ERA in 2008 was a tough season to swallow.
whopping $126 million contract
6. Josh Hamilton
Yes, we have to go right back to those LA Angels, as they made another big investment in a slugger named Josh Hamilton in 2012. Hamilton had a renaissance stretch of five years in Texas, where he was one of the premier sluggers in the MLB.
However, it just seemed like he wasn't a great fit in Anaheim from the moment he got there. From 43 home runs in his last season as a Ranger to just 21 in his first season as an Angel is a steep drop-off. He even played three additional games to get to 21.
Injuries took him out for much of his second season with the Halos, and they quickly moved on from him after that.
Los Angeles Angelsmassive $125 million contract
5. Jason Bay
Bay was a three-time All-Star by the time he got signed to go to Queens. He had done well in a couple of other East Coast stops in Pittsburgh and Boston. So the New York Mets thought that they had a shoo-in of a star outfielder.
Injuries came in basically right away, as he never was able to get off a full season as a Met. His contract was for four years, but it kind of seemed like he had only played one.
4-year, $66 million contractNational League Rookie of the Year
4. David Wright
This is a little bit more of a somber entry, as I do think everyone agrees that the big one hundred thirty-eight million dollar contract given to David Wright was a deserved one.
However, his career didn't last much longer after that. Spinal stenosis got in the way of him playing a full season after signing that contract. So the Mets never really got to see him at his best.
signed a huge $138 million contract
3. Rick Ankiel
I think we can applaud Rick Ankiel for making a transformation that turned him from a mediocre pitcher into a solid slugger. There was never really a big commitment from the St. Louis Cardinals, as they only gave him one-year deals.
But $2.8 million for a player that never played a full season in his entire career is a lot for that time. He wasn't exactly an everyday player, but he also wasn't exactly a bench player, so it kind of put his contract negotiations in a bit of a gray area.
2. Rusney Castillo
This is probably the most puzzling contract on this list. Prospects are definitely at a premium in baseball. But they still are just that.
Prospects. Rusney Castillo was a top prospect in the Boston Red Sox organization, and they believed in him so much that they gave him a seven-year, $72.5 million deal.
How many MLB games did he end up playing? Just 99. He never really realized the potential that the Red Sox saw in him when he was younger.
7-year, $72.5 million dealplaying just 99 games
1. Jacoby Ellsbury
Jacoby Ellsbury was one of the premier center fielders in the MLB when he signed a big seven-year, $153 million deal to go from Boston to the Bronx. Yeah, that is one of the more painful places for Red Sox fans to see their players go.
But maybe a curse followed him instead of staying in Boston. Injuries took a toll pretty early on in that contract as he saw his production dip well below what it used to be. Guys who rely on speed like Ellsbury need to stay in tip-top shape.
Injuries can hurt them a little bit more than others. That's what happened here. And that's why the Yankees will regret that contract for a while.
New York YankeesYankees signed him to a 7-year, $153 million deal
