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It says a lot about the inherently risky nature of $100 million contracts that we had a lot more than just 10 to choose from when we made our list of the 10 worst in MLB history.
Lest anyone think it’s all bad, however, it’s now time for the opposite of that list.
As with the worst-of list, we considered both intent and payoff in making our picks for baseball’s 10 best $100 million deals. Basically, we were looking for contracts where good intentions ultimately met with good results for the player and the team.
Likewise, we limited ourselves to contracts that have at least five years of returns by which to judge them. We also stipulated that the player had to have actually served out the contract and that whatever returns they provided primarily benefited the original signing team.
We ultimately separated the top 10 into three different tiers. The first four, for contracts that yielded extraordinary individual production but little to no postseason success. The next three—for players who were excellent and won a World Series. The last two—for excellent players who won two World Series.
We’ll begin with some honorable mentions, and then it’s on to the top 10.
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CC SabathiaTed S. Warren/Associated Press
Jan. 26, 2001: Texas Rangers Sign SS Alex Rodriguez
The Deal: 10 years, $252 million
Setting aside his admitted use of performance-enhancing drugs, A-Rod’s first megadeal was undeniably successful as he racked up 56.4 WAR in seven years before opting back into free agency. The catch is that those gains mainly benefited the New York Yankees, not the Rangers.
March 29, 2001: Colorado Rockies Extend 1B Todd Helton
The Deal: Nine years, $141.5 million
Though the Rockies and Helton agreed to this deal in 2001, it didn’t actually begin until 2003. He was his usual excellent self that year and in 2004, but then his power began to dry up, and he averaged just 14 home runs per season between 2005 and 2011.
Dec. 20, 2008: New York Yankees Sign LHP CC Sabathia
The Deal: Eight years, $161 million
Sabathia helped the Yankees win the World Series in 2009 and finished no lower than fourth in the American League Cy Young Award voting in any of his first three seasons with the team. Yet 2011 marked the end of his initial deal, as he and the team circumvented his opt-out by agreeing to a new contract.
Jan. 17, 2014: Los Angeles Dodgers Extend LHP Clayton Kershaw
The deal: Seven years, $215 million
Kershaw immediately won the National League Cy Young Award and MVP in 2014 and continued pitching at a Cy Young-caliber level through 2017. Then his returns began to diminish in 2018, which also ended with him pivoting away from this contract to a new one.
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Emilee Chinn/Getty Images
The Deal: 10 years, $225 million
WAR Before Contract: 34.3
WAR During Contract: 30.3
Given that Mike Trout signed for $200 million more before the decade was even out, Joey Votto’s $225 million pact with the Cincinnati Reds from 2012 might seem quaint now.
At the time, though, it was only the fifth contract to eclipse the $200 million threshold. It also topped Derek Jeter’s 10-year, $189 million deal with the Yankees from 2001 as baseball’s largest extension.
The Reds locked Votto up when he was two years removed from his National League MVP campaign in 2010. And while his numbers did subsequently dip in 2011, he carried on as an elite on-base artist with a National League-best .416 OBP while also hitting 29 home runs.
The catch, as it were, was that Votto was already serving a three-year contract that wouldn’t end until 2013. His new deal would begin with his age-30 season, so the Reds essentially placed a bat on age not dealing too much damage to Votto’s hitting bona fides.
Time has mostly proven them right, as Votto has averaged a .414 OBP and clubbed a respectable 174 home runs—including 36 just last year—during his deal. He, therefore, deserves relatively little blame for how the Reds have lost more than they’ve won since said deal began in 2014.
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Frank Franklin II/Associated Press
The Deal: 7 years, $119 million
WAR Before Contract: 29.3
WAR During Contract: 32.3
The defining image of Carlos Beltran’s tenure with the New York Mets isn’t great. In case anyone’s memory needs jarring, it involves Adam Wainwright and a curveball in Game 7 of the 2006 National League Championship Series.
Nevertheless, we’ll risk rupturing the time-space continuum by opining that Beltran’s contract was good, actually.
There wasn’t much question that he deserved it when he became only the 10th player to ever sign for $100 million when the Mets scooped him off the free-agent market. He was fresh off a 2004 season marked by 38 home runs and 42 stolen bases, as well as an absolutely torrid postseason.
Though Beltran debuted with a difficult campaign in 2005, that was nonetheless one of his five All-Star seasons as a Met. He then averaged a .909 OPS, 34 home runs, 22 stolen bases and 6.9 WAR between 2006 and 2008. Waino curve notwithstanding, he also lived up to his reputation with a .978 OPS in the ’06 playoffs.
Plus, it’s worth noting that the Mets traded Beltran for Zack Wheeler in the last year of the former’s contract. Not a bad peripheral benefit to go with the overall return on their investment.
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Travis Heying/Associated Press
The Deal: 6 years, $144.5 million
WAR Before Contract: 19.9
WAR During Contract: 54.4
For the record, the 12-year, $426.5 million deal that Mike Trout signed with the Los Angeles Angels in 2019 technically wasn’t…well, wasn’t that. It was a 10-year, $360 million deal on top of the one he already had.
That one, at least, worked out brilliantly for the Angels.
Trout signed it on the heels of seasons in 2012 and 2013 that, when put together, yielded 57 home runs, 82 stolen bases and 19.4 WAR. He finished second in the AL MVP voting both years, though he was worth roughly five more WAR than actual back-to-back winner Miguel Cabrera.
What’s more, 2014 would only be his age-22 season. So even in spite of obvious talent, the fact that the Angels didn’t actually pay Trout a record amount of money for a player with so little service time was nothing short of highway robbery.
It’s a black mark that the Angels had just one winning season during Trout’s first deal, but they otherwise have no cause to regret it. Between the deal’s start in 2015 and finish in 2020, he was the best hitter and best overall player in baseball, in addition to an annual All-Star and two-time MVP.
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Matt Slocum/Associated Press
The Deal: 8 years, $152.3 million
WAR Before Contract: 18.3
WAR During Contract: 46.5
The second contract that Miguel Cabrera signed with the Detroit Tigers was never going to turn out well. And as you might have noticed in the five years it’s been active, it hasn’t.
His first deal with the Tigers is a different story.
The slugger signed it mere months after he arrived in Detroit by way of a trade with the Florida Marlins. It was the fourth-biggest contract in baseball history at the time and the second-biggest extension after only Jeter’s record-setting pact from 2001.
It was a big bet on a hitter who was already excellent, as Cabrera’s baseline over the last three seasons had been an OPS in the mid .900s and 30 home runs. Yet he was still only 24 years old, so the potential of him tapping into as-yet-unexplored upside was very real.
It took no time at all for that potential to become reality. Between 2008 and 2015, Cabrera collected six All-Star nods and two MVPs while hitting .326/.406/.574 with 270 home runs. He tacked on another nine long balls in 38 playoff games, including one in the Tigers’ ill-fated tilt with the Giants in the 2012 World Series.
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Marcio Jose Sanchez/Associated Press
The Deal: 8 years, $167 million
WAR Before Contract: 12.6
WAR During Contract: 32.2
By the time the 2012 season was over, the San Francisco Giants had all the evidence they needed to believe that Buster Posey was a once-in-a-lifetime gem behind the plate.
In 2010, he had won the NL Rookie of the Year and helped lead the team to its first World Series title since 1954. Following a crushing (and literally game-changing) injury in 2011, he came back even stronger to win the NL MVP and captain another World Series winner in 2012.
Thus, it was record money time. Though Posey’s deal didn’t quite match Joe Mauer’s historic payout for a catcher, it did set a new mark for a player with less than four years of service time.
Though Posey never came close to winning another MVP, he was an All-Star five times in six seasons between 2013 and 2018. The one exception in that stretch was 2014, in which he finished sixth in the MVP voting and won yet another ring.
Capped by an excellent final season before his retirement last November, Posey ultimately led all catchers in wins above replacement between 2013 and 2021. Not bad, considering he didn’t even play in 2020 after opting out of the shortened season.
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Eric Gay/Associated Press
The Deal: 8 years, $135 million
WAR Before Contract: 9.0
WAR During Contract: 34.1
After first breaking in with Atlanta in 2010, Freddie Freeman had good seasons in 2011 and 2012 and then made the leap to greatness in 2013. He hit .319/.396/.501 and finished fifth in the NL MVP voting.
In retrospect, Atlanta would have been justified in waiting to see if Freeman could sustain that leap before offering him the biggest contract in the franchise’s history. That it did anyway signaled a belief that, hey, if he could be that good at 23, why not at 24 and all the way through 31?
Good call.
Freeman’s 2013 season ended up forecasting a shockingly accurate baseline for his next eight seasons, across which he hit .300/.394/.526 while averaging 30 home runs per 162 games. He was an All-Star four times and the National League MVP in 2020.
As a final act, Freeman was instrumental in delivering Atlanta’s first World Series title since 1995 in 2021. He hit five home runs in the postseason, including a game-winner off Josh Hader in the NLDS and the exclamation mark in Game 6 of the World Series.
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G Fiume/Getty Images
The Deal: 7 years, $210 million
WAR Before Contract: 23.9
War During Contract: 42.3
Coming off a 2014 season that saw them go 96-66, arguably the last thing the Washington Nationals needed was another ace starting pitcher.
Led by Stephen Strasburg, Jordan Zimmerman, Doug Fister, Gio Gonzalez and Tanner Roark, Nats starters had posted a league-best 3.03 ERA in 2014. What’s more, free agency was about to claim none of those five.
And yet Washington did a $210 million deal with Max Scherzer anyway. He was about to turn 30, so it was a risky bet that he would maintain the form that led him to the AL Cy Young Award in 2013 and a subsequent All-Star berth in 2014. But if it worked out, the Nats stood to prove that sometimes overkill is underrated.
Well, all Scherzer did between 2015 and 2021 was win two more Cy Young Awards and lead all pitchers in WAR by a fairly wide margin. He was first in strikeouts by an even larger margin, tallying 264 more than the next pitcher.
Though Scherzer finished off his contract with the Los Angeles Dodgers, the Nationals certainly got the best of his postseason work. His 10 appearances—including two gritty ones in the 2019 World Series—for them in October yielded a 2.92 ERA.
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The Sporting News/Getty Images
The Deal: 10 years, $189 million
WAR Before Contract: 28.0
WAR During Contract: 41.2
Suffice it to say that Jeter was pretty well established as a star when the Yankees extended him early in 2001.
After initially debuting in 1995, he was the American League Rookie of the Year in 1996 and an All-Star in 1998, 1999 and 2000. He also won World Series rings in each of those four seasons, and his overall playoff track record already had 61 games, a .324 average and eight home runs on it.
If anything, it’s a wonder that the Yankees settled for making Jeter only the second-highest-paid player in history after Alex Rodriguez and his freshly signed 10-year, $252 million contract.
Jeter was only 26 at the time, so there was a strong chance that at least the first half of his deal would work out. But ultimately, all of it did. He was good for a .315 average and 4.4 WAR per season through 2009, and he still held the overall lead in WAR among shortstops from 2001-10 even after slipping to 1.7 WAR in 2010.
Further, Jeter also added another 86 playoff games to his resume. He hit .299 with 12 homers in those, notably hitting .407 in the 2009 World Series to earn his fifth ring.
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Elise Amendola/Associated Press
The Deal: 8 years, $160 million
WAR Before Contract: 30.0
WAR During Contract: 36.6
In the wake of back-to-back trips to the playoffs in 1998 and 1999, the Boston Red Sox won only 85 games and fell short in 2000. It was no help that their offense was third from the bottom of the AL in runs scored.
Accordingly, the Red Sox signed arguably baseball’s best hitter when they inked Manny Ramirez that offseason. His deal was the second-biggest in the sport’s history, trailing only the $252 million monster that Rodriguez had agreed to hours earlier.
Ramirez arrived in Boston after having averaged a 1.072 OPS and 42 home runs over his last three seasons with Cleveland. He didn’t have the best defensive reputation, though, so his value hinged on whether he could sustain that offensive production going forward.
For the most part, he did. He made an immediate splash in 2001 and went on to post a 1.010 OPS and 291 home runs between then and 2008, playing all but 53 of 1,136 games for the Red Sox.
Ramirez was an All-Star annually in Boston, though his greatest accomplishments for the team were in the postseason. He posted a .980 OPS and 11 home runs in 43 games, eight of which came in World Series sweeps in 2004 and 2007. Ramirez was the MVP for the former.
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Elsa/Getty Images
The Deal: 7 years, $100 million
WAR Before Contract: 20.8
WAR During Contract: 65.9
Though Mark McGwire saw him for what he was about to become, Albert Pujols caught everyone else off-guard in his debut season with the St. Louis Cardinals.
He was the unanimous NL Rookie of the Year as a 21-year-old in 2001, and he ended up posting a 1.025 OPS and 114 home runs between then and 2003. In so doing, he joined Jimmie Foxx and Eddie Mathews as the only players with at least a 1.000 OPS and 100 home runs between the ages of 21 and 23.
So, the Cardinals made Pujols just the ninth $100 million player in history. He just had to keep doing what he was doing through 2010, and maybe into 2011 if the Cardinals saw fit to exercise his option for that year.
What Pujols ended up doing in the regular season is impressive enough. Particularly between 2004 and 2010, he hit .330/.432/.630 with an average of 42 home runs per season. He was an All-Star annually and the NL MVP in 2005, 2008 and 2009.
In the postseason, Pujols tacked on a 1.112 OPS and 16 home runs in 61 games. The Cardinals won two of the three World Series that he was a part of, including the one in 2011 that was partially aided by his three-homer outburst in Game 3.
Stats courtest of Baseball Reference and FanGraphs.
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