The Winter Meetings have always represented one of my favorite stops on the MLB calendar because I’ve always been enamored with player transactions — whether it be trades, free-agent signings, the Rule 5 draft, the Contemporary Baseball Era Committee voting in members of the Hall of Fame and, yes, even the draft lottery. There are just so many exciting events, surprises and disappointments at the Winter Meetings.
It’s also great to see all the front offices and on-field leaders for the 30 teams in the same place at the same time because it’s the only time of year that it happens in person.
There are high expectations for this year’s Winter Meetings with so many top free agents still on the market like star hitters Kyle Tucker, Kyle Schwarber, Pete Alonso, Alex Bregman, Bo Bichette and Cody Bellinger and star pitchers like Framber Valdez, Ranger Suárez, Tatsuya Imai, Zac Gallen, Edwin Díaz and Robert Suarez.
Then there is the possibility of big names being traded like the Tigers’ Tarik Skubal, the Brewers’ Freddy Peralta, the Twins’ Joe Ryan, the Red Sox’ Jarren Duran, the Phillies’ Alec Bohm, the Marlins’ Sandy Alcantara, the Rays’ Yandy Díaz and Drew Rasmussen, and the Mets’ Jeff McNeil.
So while some are filling out their holiday lists with presents they’d like to receive, I do something different and put together my wish list of what I’d like to see happen at the Winter Meetings. While you check my list twice, let me know if it’s naughty or nice, and give me your own Winter Meetings wish lists in the comments below.
12 major free-agent signings I’d like to see happen
Kyle Tucker to the New York Yankees for 10 years, $427 million
As long as Tucker is willing to play left field, I think he’d be the perfect fit at Yankee Stadium for the next decade. He’s a five-tool player who does everything above average. He’s not a face of the franchise type but they don’t need him to be because they already have Aaron Judge. That contract may seem like a lot of money, but think about it this way — it’s a savings of $338 million over what Juan Soto was paid last offseason.
Kyle Schwarber signs with the Cincinnati Reds for 5 years, $160 million
Signing Schwarber, who grew up in Middletown, Ohio, would shock baseball and be a game-changer for the Reds’ offense and their clubhouse. I think he probably returns to the Phillies, but I can wish this for Reds fans, can’t I?
Pete Alonso brings his 40-home run bat to Fenway Park, becomes the Boston Red Sox everyday first baseman
Alonso’s leadership, power and willingness to play every day would rub off on all the young Red Sox players and he’d take the pressure off rising star Roman Anthony. The Red Sox might need to refurbish the Green Monster with all the dings Alonso would put in it over the next several years.
Framber Valdez to the New York Mets for 7 years, $218 million
The Mets need an ace at the top of the rotation and Valdez can be just that. His high ground-ball rate and ability to miss bats, combined with his ability to pitch in big games, bode well for him pitching in Queens.
Bo Bichette staying in Toronto makes too much sense not to happen. (Andy Lyons / Getty Images)
Bo Bichette returns to the Toronto Blue Jays on a 7-year, $189 million contract
A Bichette reunion would allow the Blue Jays to run it back and keep the Vladimir Guerrero Jr./Bichette combination for years to come. Bichette wants to be there and they want him there — let’s get it done.
Alex Bregman signs with the Detroit Tigers on a 6-year, $182 million pact
The Tigers just missed on Bregman last winter but they won’t this time around. Bregman would bring his leadership, mentoring abilities and winning qualities to the Tigers’ clubhouse. Fun fact: The Tigers haven’t had a team captain since George Moriarty, who had the role from 1912-15. If they sign Bregman, would he become the first in over 100 years?
Ranger Suárez signs with the Baltimore Orioles on a 6-year, $164 million contract
The Orioles learned the hard way in 2025 what happens when you neglect the pitching market in the offseason. They can’t waste the primes of players like Gunnar Henderson and Jackson Holliday by failing to build a strong rotation.
Tatsuya Imai signs with the Detroit Tigers on a 7-year, $154 million contract
The Tigers might lose Skubal (see below) and are waiting on the return of Jackson Jobe from Tommy John surgery, but they get a top-shelf arm to help them make another run at a World Series.
Cody Bellinger surprises and signs a 6-year, $168 million deal with the Pittsburgh Pirates
The deal will shock everyone, because the Pirates would actually be spending money and Bellinger would be willing to go there. The deal won’t include a no-trade clause, which will make Bellinger a main character in the trade rumor mill for the life of the contract.
Edwin Díaz leaves the Mets but stays in New York, joining the Yankees on a 5-year, $88 million pact with escalators that take the deal to $100 million
The Subway Series gets a new twist, as the New York teams swap closers. The Yankees take a risk with a five-year deal for a reliever but the immediate boost to the back end of their bullpen will be significant.
Zac Gallen inks a 5-year, $135 million deal with the Atlanta Braves
Once Gallen joins the Braves, their pitching room immediately makes adjustments with his mechanics and gets him back on track.
Robert Suarez signs with Los Angeles Dodgers on a 5-year, $80 million pact
Suarez stays in the NL West and becomes the Dodgers’ closer with Roki Sasaki moving to the rotation.
10 major trades I’d like to see
The Tigers trade Tarik Skubal to the Dodgers for starting pitchers Tyler Glasnow and Emmet Sheehan and outfielder Zyhir Hope
The Dodgers’ rotation goes from special to legendary with the addition of Skubal and his back-to-back Cy Young Awards. The Tigers say goodbye to their ace but add another top-of-the-rotation arm who is signed for three seasons, a young starter they can slide right into the rotation and a high ceiling prospect who eventually could form a dynamic outfield with Riley Greene and Max Clark.
The Brewers trade Freddy Peralta to the Yankees for right-handed pitcher Will Warren and shortstop/utility player José Caballero
Peralta helps the Yankees weather the beginning of the season while some of their returning starters recover from surgeries, and then gives them a dangerous arm down the stretch to pair with Gerrit Cole, Carlos Rodón and others. The Brewers get a young, controllable starter and a shortstop who can give them better offensive production than they received from Joey Ortiz in 2025.
The Twins trade Joe Ryan to the Mets for pitcher Brandon Sproat, infielder Luisangel Acuña and catcher Yovanny Rodriguez
The Twins’ teardown continues, though they add a nice trio of young players to build on. The Mets get a reliable arm for the top of their rotation.
Adding Hunter Greene would give the Red Sox a powerhouse rotation. (Dylan Buell / Getty Images)
The Reds trade Hunter Greene to the Red Sox for outfielder Jarren Duran and pitchers Payton Tolle and Jedixson Paez
Boston continues to add to their starting rotation cabinet, giving them an intimidating top three with Garrett Crochet, Sonny Gray and Greene. The Reds get a dynamic table-setter for the top of their lineup, one pitcher who can step into the rotation immediately and another for the development group to work with.
The Padres acquire starting pitchers Drew Rasmussen and Shane Baz from the Rays for catcher Ethan Salas and right-handed pitchers Miguel Mendez, Humberto Cruz and Bradgley Rodriguez
With the status of Yu Darvish up in the air and Michael King testing free agency, the Padres need to rebuild their rotation quickly. Rasmussen and Baz give them two arms to slot in right away, while the Rays get the high-upside catcher Salas, as well as young pitching talent to develop.
The Cardinals trade second baseman Brendan Donovan and outfielder Jordan Walker to the Royals for left-handed pitcher Kris Bubic and right-hander Ben Kudrna
A cross-Missouri trade gives Donovan and Walker a chance to compete for an AL Central title, while the rebuilding Cardinals add two pitchers with team control remaining. Donovan will pair with Bobby Witt Jr. to give the Royals an elite middle infield and Kansas City will get a shot at unlocking Walker’s immense potential.
The Marlins trade right-handed pitcher Sandy Alcantara to the Yankees for outfielder Spencer Jones and shortstop Kaeden Kent
The trade comes immediately after the Yankees sign either Kyle Tucker or re-sign Cody Bellinger (assuming the Pirates deal doesn’t come to pass) and Alcantara can join Peralta in a revamped Yankees rotation. The Marlins get one of the most intriguing power-speed prospects in the game and a prospect in Kent who was a third-round pick in 2025 and is the son of a potential Hall of Famer (Jeff Kent; see below).
The Guardians trade left fielder Steven Kwan to the Dodgers for outfielder Josue De Paula
The Dodgers will love the Gold Glove-winning Kwan, who at the plate also provides them more traffic for the dangerous middle of their lineup, while the Guardians win the deal in the long run by gaining a potential middle-of-the-order star in De Paula.
Yankees acquire second baseman Ketel Marte from the Diamondbacks for right-handed pitcher Elmer Rodríguez and second baseman Roderick Arias
New York then moves Jazz Chisolm to third base and plays Marte at second. Marte reached base at a .376 clip last year with 28 homers. Imagine what he’d do at Yankee Stadium. The D-Backs get back two top prospects and open a spot for Jordan Lawlar on their infield.
Nationals deal left-handed starter MacKenzie Gore to the Giants for left-handed pitchers Jacob Bresnahan and Carson Whisenhunt
The Giants are looking for moderately priced starting pitchers with upside and no long-term commitment, and the Nationals are seeking controllable young starting pitchers in return, making this trade a good fit.
My wish list for the Hall of Fame and some special awards
Hall of Fame vote
The Contemporary Baseball Era Committee will vote on adding new players to the Baseball Hall of Fame on Sunday. There are eight players up for voting but each voter can only pick up to three players for inclusion (to get in, a player needs to be on at least 75 percent of the ballots). Although I do wish all eight players get in at some point, I realize it’s mathematically impossible that they all get in this Sunday. A best-case scenario is that three of them get elected (more likely, it will be two or fewer).
Therefore, despite my readers’ disgust, I’m going to wish that Barry Bonds, Roger Clemens and Gary Sheffield are voted in. All three have the numbers for the Hall of Fame, but none were elected via the writers’ ballot primarily because of allegations of PED usage. I understand that argument. However, I am also pretty certain that multiple players already in the Hall of Fame were users; there just were never any public allegations against them. I am of the belief that the best players should get into the Hall of Fame since it’s a museum and the Hall should also include with the player display all of the information that links them to PED usage to be transparent about it. MLB never suspended any of these players due to a failed PED test.
The on-field cases for Bonds, Clemens and Sheffield speak for themselves. Bonds is the second-best player I’ve seen in my lifetime, behind Shohei Ohtani, and the best hitter with power I’ve seen in person. He had a career bWAR of 162.8 with 762 home runs, 514 stolen bases and an OPS+ of 182. Clemens won 354 games with a staggering 4,672 strikeouts, a career ERA of 3.12 and bWAR of 139.2. Sheffield had some of the best bat speed I ever witnessed in my years as an evaluator, and he also put up 509 homers, 253 stolen bases, a career OPS of .907 and a career bWAR of 60.6. He had a special, clutch bat and was a winning player.
To be clear, I’m wishing for the three to get in because they were the three best players I personally witnessed during my career and I don’t think we’ll ever know which players in that era used PEDs and which ones didn’t.
In terms of the other candidates, Jeff Kent, who has no link to PEDs, is the most likely to be voted in by this committee. It’s hard to argue with a 55.4 career bWAR and 377 homers while playing mostly second and third base.
Don Mattingly had a Hall of Fame career, but thanks to a balky back, his peak as a player was over a shorter period of time than most Hall of Famers, which impacted his overall counting stats. It wasn’t his fault he had injuries, but that’s why he hasn’t gotten in. Perhaps the committee will give him a pass for that.
Dale Murphy should be in the Hall since Harold Baines is in. Murphy played 18 years with a 46.5 bWAR and 398 homers with a 121 OPS+.
Carlos Delgado fell short of 500 homers by only 27 and still had a career bWAR of 44.4 with an OPS+ of 138, which makes him a close miss for me, as well as Fernando Valenzuela, who had 2,074 strikeouts, a career 3.54 ERA and brought Fernandomania to baseball but doesn’t quite stack up with the pitchers in Cooperstown.
Ultimately, I’d rank the eight candidates this way:
- Barry Bonds
- Roger Clemens
- Gary Sheffield
- Jeff Kent
- Don Mattingly
- Dale Murphy
- Carlos Delgado
- Fernando Valenzuela
Career achievement awards
Ford C. Frick Award
I hope this award goes to Dan Shulman, the former ESPN Sunday night TV play-by-play announcer who now does play-by-play for the Blue Jays. I got to call a playoff series with him during my ESPN Radio days, and it was one of the highlights of my career. He has the voice, knowledge and passion like no other, and he sets his analysts up to be stars. It’s his time to shine and I hope he gets it this year and doesn’t have to wait. It’s only a matter of time before he gets in, so let’s make it happen now!
BBWAA Career Excellence Award
I wish for this award to go to Ken Rosenthal of The Athletic for his tireless and meritorious contributions to the field. No one works harder, is more connected and is a bigger team player than Ken.
MLB Draft lottery
The 2026 MLB Draft lottery will take place at the Winter Meetings on Tuesday, Dec. 9, and here is how I wish the lottery to unfold:
The No. 1 pick would go to the Athletics, who have only a 6.55 percent chance of securing the top pick. They’ve lost out in the lottery in past years, but my wish is that the luck turns their way this year as they get ready to move to Las Vegas in a few years.
The Pirates, Twins and White Sox land picks two-three-four, which works well since they had the best odds of getting the No. 1 pick.
The two Florida teams — the Marlins and Rays — grab picks five and six and celebrate by drinking Florida orange juice.
The two mid-Atlantic teams — the Braves and Orioles — get picks seven and eight.
Finally, the two Missouri teams — the Cardinals and Royals — round out the top 10.