Christmas week is often thought of as the time MLB executives take a break from the trades and signings of the baseball offseason — but that is not always the case.
As the holidays arrive with some of the biggest names in the 2025-26 free agent class looking for new teams, we went back and found 10 times that the MLB hot stove lit up and added some additional reason for cheer (or jeer) for fans everywhere.
(Note: These are moves made since 1990 during the week that included Christmas)
1. Los Angeles Dodgers sign RHP Yoshinobu Yamamoto for 12 years, $325 million (Dec. 27, 2023)
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It’s just not recency bias that put this deal atop our list because Yamamoto is one of the best pitchers in the game, has two rings, is coming off an especially strong playoff run, and got his contract after a multipart bidding battle with a number of big-market teams offering deals in the same ballpark as the Dodgers.
Though the next deal on this list seemed like maybe not a great idea at the time and that view was quickly vindicated, signing Yamamoto was seen as a great investment at the time of signing, even if the number was higher than anyone expected heading into the winter.
2. San Francisco Giants sign LHP Barry Zito for seven years, $126 million (Dec. 29, 2006)
Zito also signed the biggest deal for a pitcher at the time, but looking back with today’s knowledge of his peripherals (6.2 K/9, 4.0 BB/9 in 2006 for Oakland before this contract) and what that kind of pitcher would get now makes it more obvious why some thought this was too much money even at the time.
This contract was a disaster, with Zito posting 6.5 WAR total in his seven seasons with the Giants. He made only three more big league appearances after this deal ended, all in a 2015 return to the A’s.
3. San Diego Padres acquire Steve Finley, Ken Caminiti and four others from Houston Astros for Derek Bell, Phil Plantier and four others (Dec. 28, 1994)
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This was a huge trade that went on to affect pennant races and included a future MVP. Finley was a good player before this but continued that, posting 5.4 WAR in 1996. Caminiti was also a strong player who took a step forward after this deal, posting a 7.5 WAR season with 40 homers in winning the NL MVP award in 1996. The Padres made the 1998 World Series in the wake of this deal. Bell, who appears in another trade later in this list, was a nice player who eventually had a career year with 5.7 WAR for the Astros in 1998.
4. Milwaukee Brewers acquire Zack Greinke from Kansas City Royals in five-player trade (Dec. 19, 2010)
Greinke was nearing free agency after a strong start to his career with the Royals. Leading into this deal, the future Hall of Famer was among the best pitchers in baseball, posting 17.8 WAR in 2008-10, with a 3.25 ERA in 98 starts over that span. The four-player package Kansas City received in the deal included Alcides Escobar, Lorenzo Cain, Jake Odorizzi and Jeremy Jeffress, who all ended up being solid players with lots of controlled years, though Cain’s 6.1 WAR season in 2015 stands as the best performance of the group.
5. Mark McGwire re-signs with Oakland Athletics for five years, $28 million (Dec. 24, 1992)
McGwire burst onto the scene with a 5.1 WAR season and 49 homers as a 23-year-old in 1987, eventually posting 26.2 WAR before free agency. That total is among the best in recent memory with the best young free agents (Manny Machado, Bryce Harper, etc.) usually putting up a total in the mid-to-high 20s. McGwire hit the open market and opted to return to the A’s, eventually being traded to the Cardinals during the last year of this extension for the part of his career we all remember in detail.
6. Atlanta Braves acquire LHP Chris Sale and cash from the Boston Red Sox for IF Vaughn Grissom (Dec. 20, 2023)
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The only reason likely Hall of Famer Sale doesn’t rank higher on this list is because this deal wasn’t a high-profile move at the time, as evidenced by the return. Sale had made 31 starts over the previous three seasons combined then made 29 starts his first year with the Braves in winning the 2024 NL Cy Young Award. This also changed his HOF case significantly, putting up 10.0 WAR in two seasons with the Braves when there were some in the industry who thought his career might’ve been on its down slope before this trade.
7. Mike Leake signs five-year, $80 million deal with St. Louis Cardinals (Dec. 22, 2015)
I could use a number of higher-end, but not precedent-setting FA pitcher deals here, like Hyun Jin Ryu (four years, $80 million with the Blue Jays), Sean Manaea (three years, $75 million with the Mets) or Kevin Millwood (five years, $60 million with the Rangers). Leake’s deal was used as a contract comparable for a number of good-not-great pitchers for years after this, the spiritual successor to the Gil Meche deal (five years, $55 million with the Royals) before the 2007 season.
8. New York Mets acquire Mike Hampton and Derek Bell from Houston Astros for Octavio Dotel, Roger Cedeno and Kyle Kessel (Dec. 23, 1999)
Hampton was coming off a second-place NL Cy Young finish (behind Randy Johnson) and 4.9 WAR season headed into a walk year. He then posted 4.6 WAR for the Mets before hitting free agency and signing an eight-year, $121 million deal with the Rockies before his precipitous drop-off. Bell was near the end of his career, a couple of years away from “Operation Shutdown.” Dotel was a hot prospect who had a nice run as an ace reliever after this until he became more well known for playing on 13 big league teams.
9. Tim Raines traded to Chicago White Sox from Montreal Expos in five-player deal then inks three-year, $10 million extension (Dec. 25, 1990)
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Hall of Famer Tim Raines had a fantastic dozen years with the Expos to start his career, posting 48.8 WAR, 14th best in baseball during that span. He was traded to the White Sox and signed a three-year extension for $10 million on Christmas Day in 1990. He posted 11.5 WAR during that extension, then declined into role-player level until his retirement after the 2002 season. Outfielder Ivan Calderon was the main return for Montreal in the trade, and he was a good player for another season after joining the Expos.
10. San Diego Padres acquire Ryan Klesko, Bret Boone and Jason Shiell from Atlanta Braves for Reggie Sanders, Quilvio Veras and Wally Joyner (Dec. 22, 1999)
Klesko and Sanders were the principals here, but a year later Boone turned into a different human being, posting a 7.8 WAR season and 19.1 WAR in three seasons for the Mariners. Veras was still a solid player for another year or two after this.
Honorable mention (aka George Steinbrenner living for the action during the holidays)
Kenny Rogers, four years/$19.5 million with Yankees (Dec. 30, 1995)David Wells, three years/$13.5 million with Yankees (Dec. 24, 1996)Carl Pavano, four years/$39.95 million with Yankees (Dec. 22, 2004)Kei Igawa, five years/$20 million (plus $26 million posting fee) with Yankees (Dec. 27, 2006)Javier Vazquez traded from Braves to Yankees (Dec. 22, 2009)
The Yankees loved to spend money on pitchers around Christmas and got mixed results from this crew. Long-time New York fans might get an ulcer remembering some of these names.
