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Kelly McDaniel
Christmas week is often thought of as the time when MLB executives take a break from the trades and signings of the baseball offseason – but that is not always the case.
As the holidays approach some of the biggest names 2025-26 free agent class In search of new teams, we went back and found 10 times that the MLB hot stove lit up and added some extra reason for excitement (or fun) for fans everywhere.
(Note: Steps taken since 1990 during weeks including Christmas)
1. los angeles dodgers sign rhp yoshinobu yamamoto For 12 years, $325 million (December 27, 2023)
It’s not just recency bias that put this deal at the top of our list as Yamamoto is one of the best pitchers in the game, he has two rings, he is coming off a particularly strong playoff run and his contract was a multipart bidding battle with several big-market teams offering deals in the same ballpark as the Dodgers.
Although the next deal on this list probably wasn’t a good idea at the time and that idea was quickly proven correct, signing Yamamoto was seen as a great investment at the time, even if the numbers were higher than anyone expected going into the winter.
2. san francisco giants Signed LHP Barry Zito to seven-year, $126 million (December 29, 2006)
Zito also signed the largest deal for a pitcher at the time, but given today’s knowledge of his peripherals (6.2 K/9, 4.0 BB/9 for Oakland in 2006 before this contract) and what a pitcher like that would get now, it becomes more clear why even at the time some people thought it was too much money.
This contract was a disaster, with Zito posting a total of 6.5 WAR in his seven seasons with the Giants. He made only three more big league appearances after that deal ended, all in a return to the A’s in 2015.
3. San Diego Padres Get Steve Finley, Ken Caminiti and four others Houston Astros For Derek Bell, Phil Plantier and four others (December 28, 1994)
At the time, this was a huge trade that affected the pennant race and also involved a future MVP. Finley had been a good player before this, but he continued it, posting a 5.4 WAR in 1996. Caminiti was also a strong player who took a step forward after the 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 later in this list in another trade, was a good player who ultimately had a career year with 5.7 WAR for the Astros in 1998.
4. milwaukee brewers to acquire zack greinke From kansas city royals In a five-player trade (December 19, 2010)
Greinke was close to free agency after a strong start to his career with the Royals. Leading into the deal, the future Hall of Famer was one of the best pitchers in baseball, posting 17.8 WAR from 2008–2010, 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 turned out to be solid players with several control years, although Cain’s 6.1 WAR season in 2015 is the best performance of the group.
5. Mark McGwire re-signed with the Oakland Athletics for five years, $28 million (December 24, 1992)
In 1987 at age 23, McGwire broke out with a 5.1 WAR season and 49 homers, and ultimately posted 26.2 WAR before free agency. He is one of the best overall with the best young free agents in recent memory (manny machado, bryce harperetc.) generally put totals in the mid-to-high-20s. McGwire hit the open market and opted to return to the A’s, ultimately being traded to the Cardinals during the final year of this expansion for the part of his career that we all remember in detail.
6. atlanta braves get lhp chris sale cash from and boston red sox if for von grissom (December 20, 2023)
The only reason Hall of Famer Sale isn’t ranked higher on this list is that the deal wasn’t a high-profile move at the time, as the returns show. Sale had made a combined 31 starts over the past three seasons, then made 29 starts in his first year with the Braves in winning the 2024 NL Cy Young Award. It also significantly changed his HOF case, putting up 10.0 WAR in two seasons with the Braves, when there were some in the industry who thought his career might have been going downhill before this trade.
7. Mike Leakes signs five-year, $80 million deal St. Louis Cardinals (December 22, 2015)
I can’t use the many high-profile, but precedent-setting, FA pitcher deals here, like those for Hyun Jin Ryu (four years, $80 million with Blue Jays), shaun manea (three years, $75 million with the Mets) or Kevin Millwood (five years, $60 million with the Rangers). For years thereafter Leake’s deal was used as a comparable contract for many good-not-great pitchers, a spiritual successor to the Gil Meche deal (five years, $55 million with the Royals) prior to the 2007 season.
8. New York Mets Acquisition of Mike Hampton and Derek Bell from the Houston Astros for Octavio Dotel, Roger Cedeno, and Kyle Kessel (December 23, 1999)
Hampton was coming off a second-place NL Cy Young finish (behind Randy Johnson) and a 4.9 WAR season heading into a walk year. He then posted 4.6 WAR for the Mets before leaving in free agency and signing an eight-year, $121 million deal with the Rockies before his initial drop-off. Bale was near the end of his career, a few years away “operation shutdown.” Dotel was a hot prospect who performed well as an ace reliever after this until he became more famous for playing on 13 big league teams.
9. Tim Reigns traded chicago white sox Five-player deal from the Montreal Expos, then a three-year, $10 million extension (December 25, 1990)
Hall of Famer Tim Raines spent an impressive dozen years with the Expos to begin his career, posting 48.8 WAR, which was 14th best in baseball during that span. He was traded to the White Sox and also signed a three-year extension for $10 million on Christmas Day 1990. He posted 11.5 WAR during that stretch, then declined to a role-player status until his retirement after the 2002 season. Outfielder Iván Calderón was the main return to Montreal in the trade, and he was a good player for the second season after joining the Expos.
10. The San Diego Padres acquired Ryan Klesko, Brett Boone and Jason Scheel from the Atlanta Braves for Reggie Sanders, Quilvio Veras and Wally Joyner (December 22, 1999)
Klesko and Sanders were the principals here, but after a year Boone turned into a different man, posting a 7.8 WAR season and 19.1 WAR in three seasons for the Mariners. After this, Verus also remained a solid player for the next year or two.
Honorable Mention (aka George Steinbrenner living up to the action during the holidays)
Kenny Rogers, four years/$19.5 million with Yankees (December 30, 1995)
David Wells, three years/$13.5 million with Yankees (December 24, 1996)
Carl Pavano, four years with the Yankees/$39.95 million (December 22, 2004)
Kei Igawa, five years/$20 million with Yankees (plus $26 million posting fee) (December 27, 2006)
Javier Vazquez traded from Braves to Yankees (December 22, 2009)
The Yankees liked to spend money on pitchers around Christmas and they got mixed results from this team. Recalling some of these names may give longtime New York fans ulcers.
