MLB’s Winter Meetings begin Monday, and this offseason the anticipation is a bit higher than the past few years. Many in the industry believe the top free agents, who have been garnering offers for weeks, are close to making decisions. A flurry of signings and trades are expected at the beginning of next week.
As much fun as star free-agent signings can be, there’s nothing better than blockbuster trades and everything that comes with them, as big names and prospects change teams and sometimes money changes hands just to get a deal done.
Most people love to talk trades. From those in the industry to media members to fans, it’s fun to think about the possibilities. I appreciate how trade ideas, big and small, generate such dramatic reactions. When people hate a trade idea, I always ask them, do you like it from the other team’s point of view? I mean, you have to like it from one side or the other, or you have to like it because you think it’s fair for both sides.
A real trade should work for both teams — and often it does. For example, the recent Reds-Royals trade in which Cincinnati sent Jonathan India and Joey Wiemer to Kansas City for Brady Singer looks fair for both sides. However, we’ll probably view the deal more favorably for one side or the other a year from now; that’s how it works.
To set the stage for the big deals that could materialize next week (and beyond), I came up with some trade ideas for you to discuss, debate and analyze. Please use the comments section to weigh in — rip the trades you don’t like (and tell me how you’d change them), tell me which ones you do like, and share your own trade proposals.
Here are seven trades I’d like to see happen next week at the Winter Meetings in Dallas.
1. Red Sox land Garrett Crochet from White Sox
The rebuilding White Sox are committed to trading Crochet in an effort to acquire controllable everyday players who improve their offense for both the short term and long term. They match up well with teams like the Orioles and Dodgers but maybe match up the best with the Red Sox. A package led by Gold Glove-winning right fielder Wilyer Abreu, first baseman Triston Casas and catcher Connor Wong is probably close to what would work for both teams. The Red Sox have top prospect Roman Anthony as their long-term solution in right field, top prospect Kyle Teel as their future catcher, and they could move Rafael Devers from third to first base and replace him at third in free agency with Alex Bregman, Willy Adames or someone else. Crochet, who is under team control for two more seasons, posted a 3.58 ERA and 1.068 WHIP with 209 strikeouts in 146 innings (32 starts) last season.
2. Phillies add Ryan Helsley from Cardinals
The Cardinals are focused on rebuilding and the Phillies need a hard-throwing, impact reliever. The Phillies lost two key high-leverage relievers to free agency — Jeff Hoffman and Carlos Estévez — and have made it a priority to address that area this offseason. Helsley won the Trevor Hoffman Award winner this year as the best closer/reliever in the National League, logging a 2.04 ERA with 49 saves and 79 strikeouts in 66 1/3 innings. The Cardinals wouldn’t be able to get top pitching prospect Andrew Painter or the Phillies’ top position player prospect, third baseman Aidan Miller, in a deal. But they are trying to move Nolan Arenado and his contract, so perhaps if they package him with Helsley they could get third baseman Alec Bohm from the Phillies, which would be a much better long-term situation for St. Louis. (Bohm is 28 and under team control for two more years.) If the Cardinals significantly paid down Arenado’s contract — he’s owed $32 million in 2025, $27 million in 2026 and $15 million in 2027 — they also could probably get another prospect back in the deal, like outfielder Dante Nori perhaps. (Nori, 20, was the Phillies’ first-round pick this year.) Helsley and Arenado for Bohm and Nori?
3. Reds get Luis Robert Jr. from White Sox
The Reds could use one more bat for the middle of their lineup and Robert, who comes with three years of team control, would be the perfect fit. He would solve center field long term for Cincinnati and his power would play in the small confines of Great American Ball Park. Robert is coming off a subpar year in which he dealt with nagging injuries and there was no reason for opposing teams to pitch to him because he had no protection in the White Sox lineup. At his best, in 2023, he hit .264/.315/.542 with 36 doubles, 38 home runs, 80 RBIs and 20 stolen bases in 24 attempts. This year he batted just .224 but hit 14 home runs and stole 23 bags in only 100 games (393 at-bats). An outfield of Spencer Steer in left, Robert in center and TJ Friedl in right would be a huge upgrade for the Reds on both sides of the ball. In return for Robert, the White Sox would want some of the Reds’ top prospects, including third baseman Cam Collier (one of my favorites), shortstop Tyson Lewis and right-hander Luke Holman. The Reds have enough infield prospect depth with Edwin Arroyo and Sal Stewart to include both Collier and Lewis in the deal. The White Sox need to start getting more pitching back in the trades they make.
4. Orioles get a promising young starter, Bryce Miller, in trade with Mariners
If the Orioles aren’t able to re-sign Corbin Burnes and aren’t able to land Max Fried or Roki Sasaski in free agency, trading for a starting pitcher becomes a necessity. And if they can’t swing a deal with the White Sox for Crochet, then a trade for a young, controllable starter such as Miller, 26, makes sense. In 2024, his second season in the majors, Miller went 12-8 with a 2.94 ERA and 0.976 WHIP over 31 starts; he was worth 3.4 bWAR. Meanwhile, the Mariners desperately need a corner infield impact bat. Top prospect Coby Mayo can play either corner, with first base being his best long-term position. Last season he slashed .293/.372/.592 with 25 home runs and 73 RBIs at two minor-league levels but did most of his damage at Triple A. Mayo, 26, is major-league-ready and could win the Rookie of the Year award in 2025. I know it would be painful for the Orioles to trade one of their top prospect bats, but they need a young starting pitcher more. I know the Mariners don’t want to trade from their elite rotation, but they have no choice if they can’t — or won’t — sign an impact bat or two.
5. Astros acquire Cody Bellinger from Cubs
The Astros have needs at first base and in center field and Bellinger would solve either position for them, depending on where they decide to play him. He has Gold Glove-caliber potential at first base and is a plus defender in center field. Bellinger is coming off a down year in which he hit .266/.325/.426 with 18 homers and a 111 OPS+. He was worth 2.2 WAR a year after his 4.4-WAR first season in Chicago. He exercised his $27.5 million option for 2025 and has a $25 million player option for 2026 (or a $5 million buyout). The Cubs have Michael Busch at first base and Pete Crow-Armstrong (2.3 WAR last season with 10 home runs in 123 games) as their long-term center fielder. If the Cubs can move Bellinger’s contract it would free up money to spend elsewhere and the two-time All-Star could also bring back a couple of solid prospects, such as power-hitting third baseman Zach Dezenzo and right-hander Ryan Forcucci, a third-round pick in this year’s draft.
6. Dodgers pick up Devin Williams from Brewers
After landing another ace for their rotation in Blake Snell, it’s time for the Dodgers to address the back end of their bullpen. After missing the first four months of last season with stress fractures in his back, Williams returned in late July and dominated. He posted a 1.25 ERA and 0.969 WHIP in 22 appearances with 14 saves and 38 strikeouts over 21 2/3 innings. His arsenal includes arguably the best changeup in the sport. In return for an impact closer like Williams, the Brewers could get shortstop Gavin Lux, who would replace Willy Adames at shortstop and allow Joey Ortiz to play third base. They would also need to get a pitcher back in the deal and perhaps Justin Wrobleski, a 24-year-old lefty who posted a 3.76 ERA in 20 appearances (18 starts) between Double A and Triple A last season, would work for both teams. Williams has one more year of team control while Lux has two. Even if the Dodgers got Williams, they could still re-sign Blake Treinen; as Andrew Friedman, Brandon Gomes and company learned last year, you can never have enough pitching. And to replace Lux, the Dodgers could sign Adames to play shortstop. The rich get richer.
7. Yankees make a move for Rays’ Yandy Díaz
The Yankees have moved on from veteran first baseman Anthony Rizzo. They recognize that injuries and age have caught up with DJ LeMahieu, whom they can’t count on to be an everyday player in 2025. Therefore, if they can’t sign free agent Christian Walker, perhaps a smaller deal, like a trade with the Rays for Díaz, could make sense. Díaz will make $10 million in 2025 and has a $12 million club option for 2026 with no buyout. He turned 33 in August and last season slashed .281/.341/.414 (116 OPS+) with 14 home runs and 65 RBIs. In 2023, he led the American League with a .330 batting average and had a career-high 22 homers. He’s a professional hitter who would bat in the bottom-third of the Yankees’ lineup. In return, the Rays might be able to land two prospects such as speedy center fielder Brando Mayea and righty Zach Messinger, who could develop into a back-of-the-rotation starter. Messinger is a bit on the older side at 25 after pitching this year in Double A, but he posted a 3.06 ERA while soaking up 150 innings. He has control issues, but working in the Rays’ pitching program, he might be able to make adjustments. Mayea, a 19-year-old from Cuba, would be the key to this trade for Tampa Bay.
(Top photo of Garrett Crochet: Steph Chambers / Getty Images)
