Christmas Week in Baseball: A Time for Surprising Moves
Christmas week is often thought of as a time when Major League Baseball (MLB) executives take a break from the trades and signings of the baseball offseason. However, this 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 took a look back and found 10 times that the MLB hot stove lit up and added some additional reason for cheer (or jeer) for fans everywhere.
These moves, made since 1990 during the week that included Christmas, showcase that the MLB offseason is always full of surprises. From blockbuster trades to massive free agent signings, Christmas week has seen its fair share of exciting moves. Let’s take a look at some of the most notable ones.
1. Los Angeles Dodgers sign RHP Yoshinobu Yamamoto for 12 years, $325 million (Dec. 27, 2023)
This deal tops our list because Yamamoto is one of the best pitchers in the game, with two rings and an especially strong playoff run. The contract was a result of a multipart bidding battle with several big-market teams offering similar deals. Although the number was higher than expected, signing Yamamoto was seen as a great investment at the time of signing.
2. San Francisco Giants sign LHP Barry Zito for seven years, $126 million (Dec. 29, 2006)
Zito’s contract was the biggest deal for a pitcher at the time, but in hindsight, it was a disaster. With peripherals like 6.2 K/9 and 4.0 BB/9 in 2006, it’s clear why some thought it was too much money even then. Zito posted only 6.5 WAR in his seven seasons with the Giants and made just three more big league appearances after the deal ended.
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)
This huge trade affected pennant races and included a future MVP. Finley continued to be a good player, posting 5.4 WAR in 1996, while Caminiti took a step forward, winning the NL MVP award in 1996 with 7.5 WAR and 40 homers. The Padres made the 1998 World Series in the wake of this deal.
Notable Trades and Signings
Other notable moves during Christmas week include:
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. The future Hall of Famer posted 17.8 WAR in 2008-10, with a 3.25 ERA in 98 starts. The four-player package Kansas City received included Alcides Escobar, Lorenzo Cain, Jake Odorizzi, and Jeremy Jeffress, all of whom became solid players.
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. He posted 26.2 WAR before free agency, which is among the best in recent memory. McGwire opted to return to the A’s, eventually being traded to the Cardinals during the last year of this extension.
6. Atlanta Braves acquire LHP Chris Sale and cash from the Boston Red Sox for IF Vaughn Grissom (Dec. 20, 2023)
Sale had made 31 starts over the previous three seasons combined and then made 29 starts his first year with the Braves, winning the 2024 NL Cy Young Award. This trade significantly changed his Hall of Fame case, as he posted 10.0 WAR in two seasons with the Braves.
More Notable Moves
Other notable Christmas week moves include:
7. Mike Leake signs five-year, $80 million deal with St. Louis Cardinals (Dec. 22, 2015)
Leake’s deal was used as a contract comparable for several good-but-not-great pitchers in the years that followed. It was the spiritual successor to the Gil Meche deal (five years, $55 million with the Royals) before the 2007 season.
