Two years ago I examined $100M contracts. One of the things I regret is not saving that file on Google Docs, and I have since lost the file. I decided to redo the research, add some more contracts, and re-examine the data. Needless to say, the data is not much different than I found two years ago. You can find my full data set here, please let me know if I missed a contract or screwed one up. I took the salary data from Baseball-Reference and used their version of WAR for this post.
The Data Set
Best I can tell there are 63 $100M or larger contracts in baseball history signed prior to the 2018 season. This includes contracts with opt-outs which were exercised, and does not include deals signed as recently as 2018. I excluded recent contracts because they are too young to examine, and will bias the results. I made two big decisions on the data set. The first is: if a deal included an opt-out, I only considered the contract which was actually completed. The second is I only considered money actually paid to players, so players who forwent pay due to either Covid or PED use had that salary deducted from the analysis. Keep in mind active deals were considered as is, meaning I only considered salary paid out, I did not consider future commitments That being said, I broke the contracts down into four categories:
The Disasters (with a $/WAR of $15M/WAR or Greater)
These are deals which completely failed, and brought little to no value to the club. It is clear in these deals that the player did not live up to their contract in any meaningful way. This segment made up a little over 25% of the contracts examined, and included several doozies including two deals (Chris Davis and Ryan Howard) where the player was actual worth negative value over the course of the contract.
The Disappointments (with a $/WAR between $10-15M/WAR)
This was the smallest segment of contracts I examined, and is a mixed bag of bad contracts to solid ones, depending on your perspective. Overall only 17% of the contracts examined fell into this category.
The Solid Value Contracts (with a $/WAR between $5-10M/WAR)
This was the second largest grouping of the contracts providing what I called solid value, or about what a team would expect to pay value wise for a free agent. This includes some surprising contracts like Ken Griffey Jr’s deal, and Elvis Andrus’ extension with Texas.
The Overperformers (with a $/WAR of $5M /WAR or below)
Surprisingly the largest group in the sample, with about 28% of the sample falling into this category. This category includes a bunch of deals which are well known as good contracts including Max Scherzer’s free agent contract, and Mike Trout’s extension.
Overall, over 50% of the deals in Major League Baseball’s $100M contract sample set fell into one of the last two categories (i.e. contracts which either meet or exceed a teams’ expectations from a $/WAR perspective).
Ranking the Contracts
It’s typical for people to firmly believe these large deals almost always wind up being bad deals for teams. This is simply not the case, there are numerous examples of successful contracts (extensions, free agent contracts or otherwise) and while there are most definitely doozies in the sample set (and we’ll get to those soon enough) there are a lot more successes than people remember. This is natural: we remember pain far better than we remember pleasure. So here are the contracts ranked from best to worst (in terms of $/WAR)
Hands down the best value of any contract in the sample: the Cardinals hit a gold mine with Albert Pujols on his first extension. They signed him to this extension in 2004, and it ended in 2011. Over the course of the deal El Hombre won three MVP awards, making up the bulk of his Hall of Fame career. The Cardinals won three pennants, and two rings. I can confidently say: when teams sign a nine figure contract, this is the outcome fans and executives imagine.
There was debate on the wisdom of signing Scherzer when he wound up in Washington. Needless to say: Mad Max was worth every penny the Nationals have paid him thus far. The worst Max finished in the Cy Young voting since arriving in Washington is 5th in his first year. He’s won two Cys including a unanimous award, and also struck out 300 batters one year. Despite a long history of playoff struggles: the Nationals won the World Series in 2019, and Scherzer played a huge part in that victory.
Everyone remembers how awful A-Rod's second massive deal was for the Yankees (culminating in him being suspended for steroids, and admitting to using steroids in the past), but let's also be real here: Alex Rodriguez was really, really, good. Better than Derek Jeter, and arguably the best shortstop in baseball history. This contract comprises the bulk of A-Rod's best seasons, and while the Yankees failed to win a World Series: A-Rod won three MVP awards over the course of this contract. I cannot imagine this realistically being labeled anything less than a success.
Miggy came over from Florida, and promptly started to dominate the AL Central, and inked a massive contract with Detroit. Cabrera won two MVP awards, and earned a triple crown. The Tigers made the World Series once (and Miggy terrorized the Indians) over this contract. They ruined to savor from this contract by handing Miguel a putrid contract we’ll get to at the end of this list.
6. Dustin Pedrioa, $84M or $88.8M for 13.7 WAR ($2.5M or $2.8M)
I docked some points from this contract since it was signed a relatively long time ago, but Carlos Beltran was dynamite for the Mets over this contract. Beltran started out hot, and declined a bit as the contract aged (which is to be expected with most of those deals). The Mets never got it together with Beltran, and they traded him to San Francisco at the end, but Beltran was not at fault for New York’s second teams’ struggles.
This deal is a bit tougher to evaluate since it's the only deal, I believe, signed in the '90s. However, Kevin Brown was phenomenal over the course of this contract. While Brown did not win any major awards (and his teams did not win in the postseason) Brown was excellent the first two years, and quite good two other years over the course of this contract.
The Ramirez contract is a tale of two Manny's. The first Manny was a Hall of Fame, transcendent, hitter who's teams never lost and who was a massive part in three pennants, and two World Series. A player who took a .500 team on his back and waltzed them into the playoffs. The other Manny was a gigantic pain in the neck who was almost dumped several times due to his antics. His deal was well worth it, and I'll never forget the dread of facing Manny in 2007.
10. C.C. Sabathia, Yankees, $63.6 for 17.4 WAR ($3.6M/WAR)
OK, we come to our second opt out, but our first opt out which cuts short a contract to less than $100M. As I stated initially: opt outs are part of the contract, so they should be included in our analysis. If we end Sabathia's initial contract at the time he renegotiated his deal (i.e. opting out of the first, and entering the second), the deal looks stellar. Sabathia was not quite Cy Young worthy in any of the three seasons, but he was darned close. Sabathia was also ALCS MVP in 2009, and led the Yankees to a World Series that year. Overall this is a successful contract.
11. Zack Greinke, Dodgers, $70M for 17.7 WAR ($4M/WAR)
Another opt out: Greinke signed with the Dodgers after leaving the Angels, and for those four seasons Greinke was fantastic. Greinke started slow, but picked up speed and ended the contract with a superb season, where he led the league in ERA and WHIP. He opted out of that contract (a deft move) and signed another contract which will come later on this list (but unlike most second deals: it's so far not a bad one).
12. Derek Jeter, Yankees, $189M for 41.2 WAR ($4.6M/WAR)
I deducted points for this deal because it's not over yet, and since the contract is not quite over yet. Then again, with only one more year remaining on Freeman's contract: there's a chance Freeman's standing improves. However, Freeman has played at a Hall of Fame level the past few years, and this season took home an MVP award.
14. Buster Posey, Giants, $122.8M OR $131M for 29.1 WAR ($4.2 or $4.5M/WAR)
This deal has two different evaluations. In the first I excluded the 2020 season since Buster Posey did not play. In the second, I included Posey's pay because he still technically got paid for that season. I wasn't sure how to calculate because the Covid pandemic is an unusual situation. Either way, the deal is still a steal for the Giants, and Posey still led his team to the World Series and won an MVP over the course of the contract. There's one year remaining on the deal, with an option. Given Posey's position (catcher) and recent production I fully anticipate this falling lower on the list, at least a bit.
15. Kyle Seager, Mariners, $69.2M for 19.5 WAR ($3.5M/WAR)
An under the radar success story, sadly the Mariners have not translated two quite good values into a successful team.
This deal is not quite starting out as harmoniously as you'd hope. There are several opt outs in this deal, so we shall see how this deal winds up. Stanton is one of the most talented players in baseball, but he's also 30. He did win an MVP his final season in Miami.
There are several years left on this deal, three years to be exact. The biggest concern for Votto is his defense is declining, and while he can still draw walks quite well: I don't think he can get on base well enough to recover from declining power and defense. If he can move to DH that might help him.
This deal almost looked bad, but Verlander bounced back, won a Cy Young Award, and won a World Series in Houston.
21. Jason Giambi, Yankees, $115M for 22 WAR (5.2M/WAR)
22. Clayton Kershaw, Dodgers, $221.9M for 33.9 WAR ($6.6M/WAR)
Kershaw never could quite translate his regular season success to the postseason, but Kershaw won a Cy Young, an MVP and a ring over this contract while being worth every penny. That's success.
Lee won the Cy Young in 2008, his best years came in Philly, and Lee was a darned good postseason pitcher.
This one surprised me, but when healthy: Tulo was a great player. The value was there, everything else wasn't.
25. Matt Holliday, Cardinals, $130.7M for 20.7 WAR ($6.3M/WAR)
26. Stephen Strasburg, Nationals, $88M for 15 WAR ($5.9M/WAR)
There's a long way to go on this one, but I remember when he debuted: he's incredibly talented and the Nationals did just win a World Series with Strasburg, and he was the World Series MVP.
27. Elvis Andrus, Rangers, $92.5M for 17.6 WAR ($5.3M/WAR)
This deal has one year remaining, and the Rangers have not taken advantage of the good value attained in the deal.
On pure dollars to WAR: these deals are about average to slightly below average. I rank them above similar deals (and deals with better dollars to WAR) because they both succeeded in their goals: end a World Series drought. Lester for the Curse of the Billy Goat, and Texiera helped end the lengthy drought the Yankees experienced in the 2000s decade. Neither are the best 'deals' but both were resounding in their strategic success.
30. Masahiro Tanaka, Yankees, $140.5M for 17.6 WAR ($8M/WAR)
This deal is about what you can expect from a nine figure contract. Greinke has been excellent over the course of the deal, and Zack shows no signs of slowing down. At age 37 we should anticipate Greinke to decline, but he doesn't need to be superior to make this deal worth it.
On a pure dollars to WAR view: this is one of the better deals in the sample. From a practical perspective: Cano tested positive for PEDs, and the Mariners and Mets have not gone anywhere over the course of this contract.
The Twins hoped they would get peak Mauer over the course of the deal, but unfortunately Mauer declined and was forced to move from catcher to first base, which limited his value. However, it was not a terrible deal in the end.
35. Ken Griffey, Jr, Reds, $99.5M for 13.3 WAR ($7.5M/WAR)
This deal gets a worse rep than it deserves because of how good Griffey was in Seattle, but The Kid was better than you would think in Cincy.
36. Johnny Cueto, Giants, $67.5M for 8.4 WAR (7.7M/WAR)
Cueto’s first season in San Francisco props this deal up. We’ll see if Cueto can bounce back in his last season, which will determine if this deal was average or a failure. The Giants were unable to replicate their every even year trend in his inaugural season in the Bay, and their performance has declined with Cueto’s.
37. Johan Santana, Mets, $137.5M for 15.3 WAR ($9M/WAR)
This looks better than it is: Longoria has been in steep decline lately, and I question his ability to rebound in his mid-30s. That’s not impossible of course, Longoria is a Hall of Fame talent although he’s probably just off that pace at this point.
39. Jose Reyes, Marlins/Blue Jays, $106M for 9.9M ($10.7M/WAR)
40. Felix Hernandez, Mariners, $175M for 16.3 WAR ($10.7M/WAR)
Braun actually aged better than I expected but not well enough to make this deal a true success, the bigger issue for me is Braun’s awful PED scandal. From a $/WAR perspective this is not awful.
42. Carlos Lee, Astros, $99.5M for 8.4 WAR ($11.8M/WAR)
44. David Price, Red Sox/Dodgers, $121M or $132.5M for 10.4 WAR ($11.6 or $12.7M/WAR)
Price is getting older, and opted out of the 2020 season. I don't expect great things from this contract going forward.
45. Shin-Soo Choo, Rangers, $116.8M for 8.5 WAR ($13.7M/WAR)
46. Alfonso Soriano, Cubs, $133M for 9.1 WAR ($14.6M/WAR)
47. Jayson Werth, Nationals, $126M for 9 WAR ($14M/WAR)
A poster boy for the poor nine figure contract deal: Werth was signed to help bring star power to the relocated Washington franchise, and the deal ended poorly for both parties. Werth did bring some productive years in the middle of the deal, but none at the level of his production in Philadelphia.2
48. Vernon Wells, Blue Jays/Angels, $126M for 8.2 WAR ($15.4M/WAR)
49. David Wright, Mets, $138M for 7.8 WAR ($17.7M/WAR)
(tie) 50. Alex Rodriguez, Yankees, $270.9M for 10.9 WAR ($24.9M/WAR)
(tie) 50. Miguel Cabrera, Tigers, $124.1M for 4.8 WAR ($25.9M/WAR)
(tie) 50. C.C. Sabathia, Yankees, $142M, 9.9 WAR
(tie) 50. Albert Pujols, Angels, $191.6M for 14.1 WAR (13.6M/WAR)
One lesson from this exercise? If you get a good deal the first time, don't squander it by giving them another deal.
54. Prince Fielder, Tigers/Rangers, $214M for 7.1 WAR ($30.1M/WAR)
55. Matt Kemp, Dodgers, $137.5M for 4.5 WAR ($30.6M/WAR)
56. Carl Crawford, Red Sox, $139.4M for 3.5 WAR ($39.8M/WAR)
57. Matt Cain, Giants, $118M for 2.7 WAR ($43.7M/WAR)
58. Josh Hamilton, Angels, $124M for 3.1 WAR ($40M/WAR)
60. Homer Bailey, Reds, $105M for 0.5 WAR ($210M/WAR)
61. Jordan Zimmerman, Tigers, $110 for 1.1 WAR ($100M/WAR)
(tie) 62. Chris Davis, Orioles, $77.5M for -6.9 WAR
(tie) 62. Ryan Howard, Phillies, $125M for -4.8 WAR
You could probably pick any of the last four players for worst contract in history, but another lesson of this exercise: do not give an aging 30 year old first baseman a fat contract. It does not end well.