MLB free agency 2024: 5 best, 5 worst starting pitcher deals since 2000

If your favorite team needs a starting pitcher or two — that list of clubs is long — this is a good offseason to have funds to spend on the free-agent market. At least six or seven starters could land contracts of $80 million or more and another dozen or so could make significant impacts on the 2024 playoff races.  

It’s an exciting time. Well, mostly.

There is, of course, always a little sense of dread because of the volatile nature of signing free-agent pitchers. The Yankees are a prime recent example. Gerrit Cole has been pretty incredible four years into his nine-year deal. On the other hand, Carlos Rodon’s first year of a six-year deal — that 6.85 ERA in 14 starts this summer — was a complete disaster. 

The good/bad tend to run in extremes, so we thought we’d take a look at both. Here are five of the best starting pitcher free-agent signings since 2000 and five of the worst. 

MORE: Predicted landing spots for Ohtani, other top free agents

If you’re pessimistic by nature, maybe focus just on the “best” but if you’re an eternal optimist looking for a hot stove tether, maybe take a glance at the debacles.

I will say this … in compiling this list, the group of candidates for the “5 worst” category was much, much larger. Stroll around for too long in that land of bad ideas and career-altering injuries and you’re liable to swear off free-agent pitchers forever. 

5 best, 5 worst free agent pitcher signings since 2000

BEST: Zack Wheeler, Phillies, 2020

Contract details: 5 years, $118 million

Thoughts: The other deals on the “best” list were great values, but Wheeler is the only one who truly rates as a steal. He’s been everything the Phillies could have possibly hoped for in the regular season — a 3.06 ERA in 101 starts for Philly — AND he’s taken it up a notch in the postseason, with a 2.42 ERA in 63 1/3 innings. That includes a 1.04 ERA in four Game 1 assignments. At 33, he’s under contract for one more year, and he’s pretty much earned a blank check from the Philadelphia front office.

MORE: Ranking the top 99 free agents in 2024 class

WORST: Mike Hampton, Rockies, 2000

Contract details: 8 years, $121 million

Thoughts: This record-setting contract — the largest in baseball history at the time — was probably a bad idea from the get-go. Hampton’s breaking stuff was electric, but breaking stuff loses its bite in the high altitude of Colorado (a lesson he should have learned from Darryl Kile’s experience there shortly before signing the contract). The Rockies should have known that and targeted another pitcher. Hampton should have known that — especially because he owned a 6.88 ERA at Coors prior to the deal — and signed elsewhere. Alas, didn’t happen. Hampton lasted just two years with the Rockies, posting a 5.75 ERA in 62 starts, before he was mercifully traded away. 

BEST: Max Scherzer, Nationals, 2015

Contract details: 7 years, $210 million

Thoughts: No lie, $210 million is SUCH a big number for a pitcher. Felt like it would be impossible for Scherzer to live up to the expectations that come along with that contract, but the future Hall of Famer didn’t just reach expectations, he surpassed them. He never missed more than five turns in the rotation in a season, won two Cy Young awards, led the NL in strikeouts three times and, of course, helped the Nationals win the 2019 World Series. And then, when he was traded away, the return included starting pitcher Josiah Gray (All-Star in 2023) and catcher Keibert Ruiz (18 homers in 2023). That is the dream scenario.

WORST: Stephen Strasburg, Nationals, 2020

Contract details: 7 years, $245 million

Thoughts: Strasburg was incredible in 2019, both in the regular season and especially during Washington’s run to the World Series title. Heroic, even. His performances were the stuff of legend, and the Nationals rewarded their former No. 1 pick — the first player overall in the 2009 draft — with a massive deal. Unfortunately, that 2019 run basically zapped everything from his right arm, and he’s only made eight starts during that seven-year deal. He’s not technically retired (that’s another story) but he’s done pitching. 

BEST: CC Sabathia, Yankees, 2009

Contract details: 7 years, $161 million

Thoughts: Sabathia didn’t just immediately provide the Yankees with a legit ace atop the rotation — he finished Top-4 in the Cy Young voting each of his first three years — but he helped the franchise win the 2009 World Series, mowing down opponents in October. Sabathia won the ALCS MVP award and fashioned a 1.98 ERA in his five playoff starts. And maybe just as important, he assumed the mantle as the team leader after Derek Jeter and Mariano Rivera retired. Sabathia’s original deal with the Yankees was for seven years, but he wound up playing 11 seasons there before hanging up the spikes after the 2019 season.

MORE: Way-too-early 2024 Power Rankings

WORST: Jordan Zimmermann, Tigers, 2016

Contract details: 5 years, $110 million

Thoughts: At the time, Zimmermann felt like just about as sure of a thing as a team was likely to find in a free-agent starter. He’d made at least 32 starts each of the past four years, with a 3.13 ERA/3.33 FIP, and he was just 29 when he signed with the Tigers. And holy cow, did his time with Detroit start out well. He had a 0.55 ERA through his first five starts with his new club, but landed on the DL with a neck strain before the All-Star break and was basically never the same. He only once made more than 25 starts and finished with a 5.63 ERA in his five seasons with the Tigers. 


BEST: Jon Lester, Cubs, 2015

Contract details: 6 years, $155 million

Thoughts: Lester was the perfect piece to the Cubs’ puzzle, the veteran with the championship pedigree — two World Series titles in Boston, with sterling numbers in October — to add to the mix of Chicago’s home-grown young stars. If the lefty had returned to the Red Sox, or taken the larger offer from the Giants, the Cubs might still be searching for that ever-elusive World Series title. But Lester chose Chicago and had a 2.02 ERA in the 2016 postseason as the Cubs broke the Billy Goat Curse with a dramatic seven-game World Series win over Cleveland. 

WORST: Carlos Silva, Mariners, 2008

Contract details: 4 years, $48 million

Thoughts: In terms of total value, there are others that could have made the list. But Silva’s here to show it’s not just the big deals that go bust. Silva had been up-and-down in his four seasons with the Twins — a 5.94 ERA in 2006, then a more respectable 4.19 in 2007 — but the Mariners liked the soon-to-be-29 year old. They’d finished with 88 wins in 2007 and saw Silva as an innings-eater who could solidify the rotation around young stud Felix Hernandez and push the M’s toward October. Didn’t happen. Silva made 28 starts in 2008, with a 6.46 ERA. Seattle plummeted from 88 wins to 61. He spent most of 2009 on the DL, posting an 8.60 ERA in 30 1/3 innings, then was traded to the Cubs in the offseason for Milton Bradley. 

BEST: Zack Greinke, Dodgers, 2013

Contract details: 6 years, $147 million

Thoughts: I know what you’re probably thinking. “Wait, Greinke didn’t pitch for the Dodgers for six years, did he?” No, he did not. But that’s because he was so very good in his first three years with the club that it was a no-brainer to exercise the opt-out clause in his contract to land an even larger contract, with the Diamondbacks. In his three years with the Dodgers, Greinke posted a 2.30 ERA. The Dodgers fell short in the playoffs all three years, but that certainly wasn’t Greinke’s fault; he made six postseason starts for the Dodgers, held opposing batters to a .186 batting average and posted a 2.38 ERA. 

WORST: Barry Zito, Giants, 2007

Contract details: 7 years, $126 million

Thoughts: This deal has long been held up right with Hampton’s as the worst-case scenario for free-agent starting pitcher contracts, which is why we’ve included this here. But the truth is, Zito’s deal wasn’t nearly as bad as Hampton’s. Yes, he finished with a 4.62 ERA with the Giants — it was 3.58 for the A’s — and he never approached his Cy Young form for any stretch of time. But he was a consistent piece of the Giants’ rotation, making at least 32 starts five times in his seven years. And his 2012 playoff performance was the stuff of legend. The Giants trailed the Cardinals, 3 games to 1, in the NLCS. Zito was brilliant in Game 5, shutting out the Cardinals — in St. Louis — on just two hits in seven innings. The Giants won Games 6-7 at home, then went on to sweep the Tigers in the World Series, with Zito nailing his Game 1 start, allowing just one run in 5 2/3 innings.

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