Kiley McDaniel covers MLB prospects, the MLB Draft and more, including trades and free agency.
Has worked for three MLB teams.
Co-author of Author of ‘Future Value’
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)
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)
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.
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.
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)
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.
Members of the Professional Hockey Players’ Association are on the verge of staging a strike in the ECHL if the union and the league cannot come to an agreement on a new collective bargaining agreement.
The PHPA announced Monday that its ECHL membership has served a strike notice that would be effective Friday, when play is scheduled to resume following the holiday break. Players voted Friday to authorize their bargaining committee to call for a strike, executive director Brian Ramsay said Monday.
“Our members have made it very clear that they’ve had enough,” Ramsay said on a video call with reporters. “Unfortunately, this is a league that would rather bully us than bargain.”
The sides appeared no closer to a resolution Tuesday based on an update from Ramsay, even after he said the PHPA offered the option of reaching a settlement through mediation or arbitration.
“The ECHL responded within minutes, rejecting any interest in this solution and demanding ‘significant movement’ and concessions from the players,” Ramsay said in a released statement. “This approach continues to align with the increased threats our membership has faced over the past 18 hours.”
CBA talks began in January, with Ramsay accusing the league of unfair bargaining practices, including most recently contacting players directly with proposals, which have been reported to the National Labor Relations Board.
“This is a league that has taken almost a year to concede that we should be entitled to choose helmets that properly fit us and are safe,” Ramsay said. “This is the league that still supplies our members with used equipment. This is a league that shows no concern for players’ travels and in fact has said the nine-hour bus trip home should be considered your day off. We have had members this year spend 28 hours-plus on a bus to play back-to-back games on a Friday and Saturday night, only to be paid less than the referees who work those very same games.”
The ECHL posted details of its latest proposal on its website Monday, saying it calls to raise the salary cap 16.4% this season, with retroactive pay upon ratification, and increases in total player salaries in future years to pay players nearly 27% more than the current cap. The league said it has also offered larger per diems, mandatory day-off requirements and a 325-mile limit for travel between back-to-back games.
“Our approach will continue to balance the need to best support our players and maintain a sustainable business model that helps ensure the long-term success of our league so it remains affordable and accessible to fans,” the ECHL said, adding that the average ticket price is $21. “Negotiations have been progressing but not as quickly as we would like.
“We have reached a number of tentative agreements and remain focused on reaching a comprehensive new agreement that supports our players and the long-term health of every team in our league.”
Taking issue with the ECHL’s offer numbers, Ramsay said inflation would have players making less than the equivalent amount in 2018, prior to the pandemic. The league said a work stoppage would result in some games being postponed and players not being paid and losing housing and medical benefits that it pays for.
Ramsay called threats of players losing their housing if there’s a strike an unfair labor practice in itself.
“Consistently in the last six or eight weeks, teams trying to intimidate and bully our members, threaten our members with their jobs, with their housing, with their work visas if they’re from out of country — different tactics like that,” Ramsay said.
Jimmy Mazza, who played several seasons in the ECHL and is now on the negotiating committee, argued that owners do not know what it’s like to travel 29 hours in a bus or to be given a used helmet.
“The top level, you know that those players aren’t being treated that way, so why are they treating us that way?” Mazza said. “To us, it’s a little bit of a slap in the face with the way these negotiations have gone for a year, when only five days ago, we get a little bit of movement on a helmet issue when it should have been done a year ago.”
The ECHL, formerly known as the East Coast Hockey League and now going just by the acronym, is a North American developmental league that is two levels below the NHL, with the American Hockey League in between. There are 30 teams, 29 of which are in the U.S. and one in Canada in Trois-Rivières, Quebec.
The AHL and PHPA have been working under the terms of their most recent CBA, which expired Aug. 31. An AHL spokesperson said the sides are very close to a new agreement.
The NHL and the NHL Players’ Association earlier this year ratified a deal that ensures labor peace through 2030.
TORONTO — Max Domi scored the winner with 8:25 remaining to snap a 23-game goalless streak and added an assist to end the Toronto Maple Leafs‘ three-game slide with a 6-3 win against the Pittsburgh Penguins on Tuesday.
Domi danced around Pittsburgh newcomer Brett Kulak for the deciding goal, a few hours after Toronto general manager Brad Treliving gave coach Craig Berube a vote of confidence for the second time this season.
“I support Craig fully. When you go through rough stretches, that’s part of the business,” he said. “There isn’t a disconnect. We all need to be better, we all recognize that, but I think we got a really good coach.”
Treliving spoke a day after the club fired assistant coach Marc Savard following two losses in two days over the weekend.
“The players have responsibility and this doesn’t absolve anybody. This is not we throw somebody out and blame that person,” he said. “It’s a change that we could make to change the dynamic, change maybe a little bit of the play.”
Nylander scored the icebreaker for his first in 11 games, midway through the first period. But Rust drew the Penguins even 44 seconds later, getting behind Nicolas Roy and Chris Tanev for a successful breakaway.
Tanev returned after a 23-game absence. He was stretchered off the ice after a collision on Nov. 1 in Philadelphia.
Toronto fired 31 shots on goal while the Penguins registered 32, with Joseph Woll picking up his sixth win in 11 starts. Pittsburgh goalie Stuart Skinner has yet to win in three starts, with 12 goals against since being traded by the Edmonton Oilers on Dec. 15.
Savard steered the Maple Leafs to the NHL’s worst power play (12 for 90 with four short-handed goals against), and on Tuesday, Toronto went 0 for 2 against Pittsburgh. Assistant coach Derek Lalonde has been tasked with fixing the team’s power-play struggles.
A federal judge has denied a motion by former Michigan co-offensive coordinator and quarterbacks coach Matt Weiss to have 10 aggravated identity theft counts against him dismissed.
Weiss, 42, was indicted in March for allegedly stealing private videos and photos of more than 3,300 student-athletes — mostly women — from over 100 universities across the country. Federal documents allege that Weiss hacked into the accounts to view and download personal or intimate photographs and videos and took notes commenting on the students’ bodies and sexual preferences.
His attorneys tried to argue that Weiss using stolen passwords is like using a stolen key to unlock a door and doesn’t equate to aggravated identity thefts. But U.S. District Court Judge Nancy G. Edmunds disagreed.
“The fact that using a house key is not identity theft only reflects that the statute was not written to cover house keys — it does not show that using another person’s login credentials without permission cannot be part of an identity-theft crime,” Edmunds wrote in her ruling.
The 10 aggravated identity theft counts carry the most federal prison time if Weiss is convicted. He also faces 14 counts of unauthorized access and is being sued in a separate case by more than 70 women who claim that he illegally hacked into their private accounts and stole their personal photos.
Weiss was fired by Michigan in January 2023, after spending the previous two seasons on Jim Harbaugh’s staff as an assistant. The former co-offensive coordinator’s alleged crimes also date back to his time with the Baltimore Ravens, where he coached for more than a decade.
Weiss faces more than 70 years in prison if convicted.