Christmas week is usually an off-calendar lull for baseball, but since 1990 a handful of blockbuster trades and landmark signings have landed during the holidays. In a Dec. 23, 2025 roundup, ESPN MLB Insider Kiley McDaniel cataloged the 10 most consequential moves made during the week that included Dec. 25, highlighting everything from 12-year free-agent pacts to multi-player swaps that reshaped pennant races. The list spans high-risk, high-reward contracts (Yoshinobu Yamamoto, Barry Zito) and trades that produced MVP seasons and postseason runs (Ken Caminiti, Steve Finley). Those episodes show that front offices have, at times, used the holiday week to swing for impact rather than rest.
Key takeaways
- Yoshinobu Yamamoto signed a 12-year, $325 million contract with the Los Angeles Dodgers on Dec. 27, 2023, following an intense multi-team bidding contest.
- Barry Zito agreed to a seven-year, $126 million deal with the San Francisco Giants on Dec. 29, 2006; he produced 6.5 WAR across that seven-year tenure.
- On Dec. 28, 1994 the San Diego Padres acquired Steve Finley and Ken Caminiti (among others) from Houston; Caminiti later won the 1996 NL MVP with a 7.5-WAR season.
- Zack Greinke was traded from the Kansas City Royals to the Milwaukee Brewers on Dec. 19, 2010; Greinke had posted 17.8 WAR from 2008–2010 before the move.
- Mark McGwire re-signed with the Oakland A’s on Dec. 24, 1992 for five years and $28 million after compiling 26.2 WAR prior to free agency.
- The Atlanta Braves acquired Chris Sale from the Boston Red Sox (Dec. 20, 2023), a deal that preceded strong Cy Young–level performance with his new club.
- Mike Leake’s five-year, $80 million contract with the St. Louis Cardinals (Dec. 22, 2015) became a reference point for solid middle-of-the-rotation FA deals.
- Tim Raines was traded to the Chicago White Sox and signed a three-year, $10 million extension on Dec. 25, 1990, during a Hall of Fame–caliber run that began in Montreal.
Background
The winter transaction window in Major League Baseball runs broadly from the end of the World Series through spring training, and front offices often schedule major announcements around payroll calendars, posting deadlines and arbitration projections. Though many teams pause activity around the holidays, the last three decades have produced notable exceptions when clubs accelerated negotiations or closed deals amid the holiday week. Those exceptions frequently involved high-profile pitchers, long-term contracts and cross-market bidding—areas where teams with financial flexibility or urgent roster needs act decisively.
Several recurring themes explain why big moves sometimes fall in the Christmas window. First, clubs with payroll space or aggressive ownership can exploit quieter moments when competition might assume negotiations are dormant. Second, posting fees and international windows can compress timelines around year-end. Third, historical precedent matters: after past headline transactions delivered immediate roster impact, other clubs have felt pressure to act fast to avoid missing out. That context helps explain why teams as varied as the Dodgers, Giants, Yankees and Padres appear multiple times in holiday-week activity lists.
Main event
At the top of the list is Yoshinobu Yamamoto’s 12-year, $325 million agreement with the Los Angeles Dodgers on Dec. 27, 2023—a deal that followed a multipart bidding battle among big-market clubs. Yamamoto arrived with a pedigree that included international success and postseason performance; the contract represented both an investment in peak talent and a long-term financial commitment from a high-spending franchise. Industry observers at the time framed the signing as a statement that elite starting pitching remains a top premium in free agency.
By contrast, the Barry Zito signing on Dec. 29, 2006 (seven years, $126 million with San Francisco) is widely viewed in hindsight as a contract that failed to deliver commensurate on-field value: Zito compiled roughly 6.5 WAR during his seven Giant seasons. The contrast between Yamamoto and Zito illustrates two central risks of winter deals: projecting future performance from past peripherals, and absorbing long-term salary for pitchers with variable outcomes.
Other holiday-week transactions produced sustained competitive effects. The Padres–Astros trade on Dec. 28, 1994 brought Steve Finley and Ken Caminiti to San Diego, catalyzing the Padres’ late-1990s run that culminated in a 1998 World Series appearance; Caminiti’s 1996 MVP season (7.5 WAR) is an immediate example of how a single trade can reshape a club’s trajectory. Similarly, the Royals’ decision to trade Zack Greinke to Milwaukee on Dec. 19, 2010 moved an emergent ace into a new context while returning controllable pieces (Alcides Escobar, Lorenzo Cain, Jake Odorizzi, Jeremy Jeffress) who produced future value for Kansas City or elsewhere.
Analysis & implications
Holiday-week deals reveal different organizational approaches to risk. Long-term, large-dollar contracts (Yamamoto, Zito, McGwire’s 1992 extension) are bets on sustained peak performance; when they pay off, they anchor championship windows, but when they do not, they create roster inflexibility. Teams with deep pockets may be willing to accept that tradeoff as part of a win-now posture. Conversely, trades that exchange present talent for controllable younger players (Greinke trade returns; Padres–Astros swap) reflect a farm-system–first model aimed at building sustained depth.
From a competitive-balance angle, holiday-week signings and trades often advantage teams that can move quickly and offer payroll certainty. The Yankees’ repeated December and late-December investments in the 1990s–2000s—documented by multiple holiday deals—illustrate how ownership philosophy and market size influence timing. That dynamic continues to matter today: clubs in contention or with impending roster holes can convert quiet calendar moments into strategic gains if they are prepared operationally.
Looking forward to the 2025–26 offseason, the presence of multiple premium free agents means another busy winter is possible. Front offices must weigh short-term upgrades against long-term flexibility; decisions made in the holidays can create ripple effects across arbitration cycles, international signings, and trade-market valuations. For smaller-market clubs, the calculus leans toward creative trade construction and player development, while large-market clubs retain the option to deploy headline signings at any calendar moment, holidays included.
Comparison & data
| Year | Move | Terms / Notable figures | Noted impact (WAR or outcome) |
|---|---|---|---|
| 2023 | Yoshinobu Yamamoto → Dodgers | 12 yrs, $325M (Dec. 27) | Immediate rotation anchor; bidding war noted |
| 2006 | Barry Zito → Giants | 7 yrs, $126M (Dec. 29) | 6.5 WAR across contract; viewed as negative ROI |
| 1994 | Padres ← Finley, Caminiti (from Astros) | Dec. 28, 1994 (multi-player trade) | Caminiti: 7.5 WAR & 1996 NL MVP; helped 1998 WS run |
| 2010 | Greinke → Brewers | Five-player trade (Dec. 19) | Greinke had 17.8 WAR, 2008–2010; Royals received controllable talent |
| 1992 | Mark McGwire re-signs with A’s | 5 yrs, $28M (Dec. 24) | Prior 26.2 WAR before free agency |
| 1990 | Tim Raines → White Sox + extension | 3 yrs, $10M (Dec. 25) | Raines had 48.8 WAR in first 12 seasons |
The table above summarizes headline deals and the most commonly cited measures of impact; WAR figures shown are those reported in the historical record for the seasons cited. Using cross-era comparisons requires caution because player valuation metrics, arbitration rules and market inflation have evolved since 1990.
Reactions & quotes
Front-office observers framed Yamamoto’s signing as an aggressive allocation of resources to elite pitching that other clubs would have to match or counter in different ways.
ESPN analysis (Dec. 2023 roundup)
Baseball historians point to the Zito contract as an example of how peripheral metrics can be misread when long-term dollars are on the table.
Independent baseball historian
Fan response to holiday deals tends to be polarized: immediate optimism for headline acquisitions and second-guessing when long-term contracts underperform.
Contemporary fan and media commentary
Unconfirmed
- Specific internal bidder offers and final counteroffers in the Yamamoto free-agent process have not been publicly disclosed; reported ranges reflect industry reporting rather than full transparency.
- Some contemporaneous reports linked the Barry Zito signing to competitive signaling by ownership; internal decision memos have not been released to confirm that motive.
Bottom line
Christmas week has produced outsized baseball headlines across eras: long-term free-agent contracts, multi-player trades and unexpected extensions have all been completed while most of the sports world assumed front offices were on hiatus. The examples from 1990 through the present show both sides of high-stakes winter activity—transformative outcomes (Caminiti’s MVP season; Greinke’s pre-trade excellence) and costly misfires (Zito’s contract performance).
For the 2025–26 offseason, fans and front offices should expect the familiar pattern: marquee pitchers and top free agents will draw the most attention, but the actual competitive edge will often come from how clubs balance immediate roster need against long-term flexibility. Monitoring transaction timing—including moves that arrive around holidays—remains essential to understanding who is positioning for next season’s pennant races.