Ranking the 15 Most Overpaid Pitchers of All Time

Pitching wins championships, but not every big contract delivers the expected results. Throughout MLB history, teams have thrown mountains of cash at pitchers, only to watch them fizzle out, get injured, or just plain underperform. From aging veterans to one-season wonders, these guys cashed in—and left their teams regretting it.

Let’s break down the 15 most overpaid pitchers of all time, ranked from “that was a bad deal” to “how did they get away with this?”

14. Barry Zito – San Francisco Giants

Contract: 7 years, $126 million (2007-2013)

Barry Zito was dominant with the A’s, but when the Giants handed him a massive deal, things went south fast. His velocity dipped, his ERA ballooned, and by the time his contract was up, San Francisco fans were just relieved to move on. At least he got a World Series ring out of it.

13. Mike Hampton – Colorado Rockies

Contract: 8 years, $121 million (2001-2008)

Paying big money for a pitcher at Coors Field? Bold strategy, Colorado. Unfortunately, Hampton’s ERA skyrocketed, and he was gone in two years via trade. Turns out, thin air and huge contracts don’t mix well.

12. Kevin Brown – Los Angeles Dodgers

Contract: 7 years, $105 million (1999-2005)

Kevin Brown was the first MLB player to score a $100 million contract, and the Dodgers didn’t get their money’s worth. He had a few solid years, but injuries and inconsistency made this a brutal overpay.

11. Carl Pavano – New York Yankees

Contract: 4 years, $39.95 million (2005-2008)

Four years, nearly $40 million, and what did the Yankees get? Four wins. Total. Pavano spent more time on the injured list than the mound, earning the nickname “American Idle” from frustrated fans.

10. Jordan Zimmermann – Detroit Tigers

Contract: 5 years, $110 million (2016-2020)

Zimmermann was solid in Washington, but Detroit paid him ace money for what turned out to be a disaster. His ERA in a Tigers uniform? A staggering 5.63. That’s one expensive batting practice pitcher.

9. Rick Porcello – Boston Red Sox

Contract: 4 years, $82.5 million (2016-2019)

Porcello won a Cy Young in 2016, but Red Sox fans will tell you that was a fluke. His ERA jumped above 5.00 in two of his four years under this deal, making him one of baseball’s highest-paid mediocrities.

8. Matt Cain – San Francisco Giants

Contract: 6 years, $127.5 million (2012-2017)

Cain was a legend in San Francisco, but once he signed this deal, his career fell apart. His ERA shot up, injuries piled on, and the Giants ended up paying a fortune for one solid year and a lot of regret.

7. Patrick Corbin – Washington Nationals

Contract: 6 years, $140 million (2019-2024)

Corbin was key to the Nationals’ 2019 World Series win, but after that? He turned into one of the worst starters in baseball, and Washington is still stuck paying him a fortune to give up home runs.

6. Johnny Cueto – San Francisco Giants

Contract: 6 years, $130 million (2016-2021)

Cueto had one fantastic season in San Francisco, but after that? Injuries, inconsistency, and a whole lot of missed starts. The Giants basically paid him ace money to be a part-time pitcher.

5. David Price – Boston Red Sox

Contract: 7 years, $217 million (2016-2022)

$217 million is elite money. David Price’s time in Boston? Not so elite. He had some solid moments but spent most of his contract injured, inconsistent, or beefing with Dennis Eckersley.

4. Stephen Strasburg – Washington Nationals

Contract: 7 years, $245 million (2020-2026)

Strasburg dominated in the 2019 playoffs, earning a mega-deal from the Nationals. Since then? He’s barely pitched. Injuries have turned this into one of the most painful contracts in MLB history.

3. Homer Bailey – Cincinnati Reds

Contract: 6 years, $105 million (2014-2019)

Homer Bailey threw two no-hitters, and the Reds thought they had their ace. Instead, he turned into an absolute mess, posting a 6.25 ERA in his final three years. Cincinnati fans are still trying to forget this one.

2. Jason Schmidt – Los Angeles Dodgers

Contract: 3 years, $47 million (2007-2009)

The Dodgers expected an ace. Instead, they got an expensive spectator. Schmidt made just 10 starts in three years due to injuries, making him one of the worst free-agent signings ever.

1. Kei Igawa – New York Yankees

Contract: 5 years, $20 million (2007-2011)

This might not be the biggest contract, but it’s easily one of the worst. The Yankees paid $46 million (including a posting fee) for 12 total MLB starts and an ERA of 6.66. He spent most of his contract in the minors while the Yankees tried to pretend it never happened.