Last week’s general managers’ meetings marked the beginning of trade talks throughout the league. Although free agency typically dominates the major-league transactions in November and early December, a blockbuster trade or two always seems to occur. This year, a lot of big names are being discussed in trade talks, but that doesn’t mean those players will be dealt. Trade talks are part of the offseason process for front offices, even though most usually don’t result in a deal.
This free-agent class is loaded with starting pitchers and power bats, but some teams won’t compete with the biggest markets in free agency — in part because of a decline in local television and streaming revenue — and instead would prefer to trade to fill their most pressing needs.
To set the stage for trade season, here are 15 notable players who could get traded this winter, along with my thoughts on them and what I’m hearing in my conversations with people across the game.
1. Vladimir Guerrero Jr., 1B, Blue Jays
The Blue Jays have given no indication they’re going to trade Vladimir Guerrero Jr. this offseason, but one National League general manager told me he believes they’ll change their mind when they realize they have little chance of extending him; after free-agent first basemen Pete Alonso and Christian Walker sign, this GM thinks the Blue Jays will be enticed by the franchise-changing trade offers they could receive for Guerrero, because their farm system needs an infusion of prospects. Guerrero is coming off a banner season in which he slashed .323/.396/.544 (166 OPS+) with 30 home runs, 98 runs scored and 103 RBIs. He’s under team control for one more season. His trade value is sky high and the Blue Jays have many areas of need. Trading Guerrero is imperative if they can’t sign him to a long-term deal this offseason.
2. Garrett Crochet, LHP, White Sox
Every front office executive I’ve talked with believes Garrett Crochet will be traded before the end of this year, and they mention the Red Sox, Orioles and Dodgers as the most likely landing spots because all three have the young, everyday position players the White Sox want in return for the 25-year-old lefty, who has two more years of team control. Crochet finished last season with a 3.58 ERA and 209 strikeouts over 146 innings. He made his first of many All-Star teams as well.
3. Zac Gallen, RHP, Diamondbacks
The Diamondbacks deny that Zac Gallen is on the trade market or that they’re looking to deal him, but the righty is eligible for free agency after next season. If they haven’t extended him and receive a strong trade offer, they have no choice but to consider it. Gallen is Arizona’s ace and he went 14-6 this year with a 3.65 ERA. However, once free-agent starters Corbin Burnes, Max Fried, Blake Snell and Nathan Eovaldi sign, the big-market teams that lose out might be willing to offer significant prospect packages for Gallen, who has finished in the top 10 of the NL Cy Young Award voting three times over the past five seasons. Gallen, who would reach free agency at just 30 years old, stands to be in a similar price range to Burnes and Fried a year from now. It’s unlikely he gets moved, but remember, every general manager has coveted prospects they wouldn’t turn down.
4. Ryan Helsley, Closer, Cardinals
Ryan Helsley was arguably the best closer in the NL this year and his trade value will never be higher. The Cardinals are rebuilding and shopping their veterans and they’d be foolish not to see what they could get in return for the two-time All-Star. Once free-agent reliever Tanner Scott signs, Helsley’s market will shoot through the roof, with the Orioles and Red Sox being among the logical fits. Helsley logged a 2.04 ERA over 65 appearances last season with 49 saves. He was worth 3.0 WAR, according to Baseball Reference.
5. Luis Robert Jr., CF, White Sox
The White Sox claim they want to build around him, but let’s be realistic: Luis Robert Jr. will turn 28 next August, he’s already halfway through his prime years and will be a free agent after the 2027 season. His trade value is high and the White Sox need to take advantage of it. If they can get seven solid-to-great prospects for both Crochet and Robert, their rebuild timeline could be expedited by two to three years. The Phillies, Red Sox and Astros make a lot of sense as trade partners for Chicago.
6. Devin Williams, Closer, Brewers
After missing the first four months of the season with stress fractures in his back, Devin 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. Batters hit .111 against his four-seamer and .162 against his changeup, which is arguably the best in baseball. He will be a free agent after the 2025 season and the Brewers’ modus operandi is to trade these types of players at least a year ahead of time. With many contending teams looking to bolster their bullpens, Milwaukee could do very well in a Williams trade if his medical reports check out OK.
7. Wilyer Abreu, OF, Red Sox
Wilyer Abreu had a special rookie season, slashing .253/.322/.459 (114 OPS+) with 15 homers. He won a Gold Glove Award in right field and was worth 3.4 WAR. So why would the Red Sox deal a player like that who has five more years of team control? Because they have another young right fielder, 20-year-old Roman Anthony, who is an even better prospect than Abreu. If Boston can put together a trade to land a strong pitcher such as Garrett Crochet, they can afford to move Abreu despite his stellar debut.
8. Sonny Gray, RHP, Cardinals
When the Cardinals signed Sonny Gray last November to a three-year, $75 million deal, they backloaded it in case they decided to trade him this offseason. He made $10 million this year but is due $25 million in 2025 and $35 million in 2026 (and his deal includes a $30 million team option for 2027 with a $5 million buyout). It’s not the type of contract that’s easy to move. The Cardinals will have to pay down the contract to find a suitor, but a trade is possible with so many teams looking for starting pitching. Gray went 13-9 this year with a 3.84 ERA and 203 strikeouts in 166 1/3 innings.
9. Yandy Díaz, 1B, Rays
The Rays hold a team option on Yandy Díaz for 2026 and are in no rush to trade him. That said, when Alonso and Walker sign, the teams that miss out on them could try to convince Tampa Bay to part with him. The Rays are looking for a left-handed hitter and if they could find the right one in a Díaz deal, they’d consider it. Díaz batted .281/.341/.414 (116 OPS+) this year with 14 homers and 65 RBIs.
10. Ryan Pressly, Closer, Astros
It’s only a matter of time before the Astros move Ryan Pressly to a team where he can once again be a closer. He lost his closing gig last offseason when Houston signed Josh Hader to a long-term contract. He filled whatever role the Astros wanted this past season, posting a 3.49 ERA over 59 appearances. But next year he will make $14 million, money that they could put toward Alex Bregman’s new contract. With a strong market for both closers and relievers, it may take time for the Astros to find the best trade for Pressly, who will turn 36 in December.
11. Nolan Arenado, 3B, Cardinals
Nolan Arenado is one of, if not the best defensive third baseman I’ve ever seen. He’s a future Hall of Famer, in my opinion. However, he’s in serious decline and will turn 34 next April. Over the past three seasons, his slugging percentage dropped from .533 to .459 to .394 and his home run output fell from 30 to 26 to just 16 this year. The 10-time Gold Glover, five-time Silver Slugger and eight-time All-Star is a shell of his former self. He is due to make $32 million this year, $27 million in 2026 and $15 million in 2027. St. Louis should trade him this offseason, or if not, at the next trade deadline if he gets off to a good start. The rebuilding Cardinals would have to pay down his salary (the Rockies are on the hook for $5 million in both 2025 and 2026) and find a taker — perhaps a team that loses out on Bregman and Willy Adames in free agency might take a chance on Arenado for the right trade and contract price.
12. Chris Bassitt, RHP, Blue Jays
The Blue Jays are not going to extend Chris Bassitt, who is signed through next season, so they should move the 35-year-old righty now while he still has trade value. Bassitt went 10-14 this year with a 4.16 ERA over 31 starts. He posted an inflated WHIP of 1.462 and was worth -0.1 WAR. However, he’s pitched at least 170 innings each of the past three seasons, and plenty of teams would take a starter who can provide those innings to save their bullpens.
13. LaMonte Wade Jr., 1B, Giants
In a departure from the previous administration, the Giants’ new front office leadership, led by president of baseball operations Buster Posey, appears to want to emphasize everyday players more than platoon types, which means they could move on from LaMonte Wade Jr., who batted .260/.380/.381 (121 OPS+) last season over 331 at-bats. He was worth 2.1 WAR. The Giants might find a fit with the Tigers, who could have Wade share playing time with Spencer Torkelson, or with the Mariners, who are trying to improve at both of their infield corner positions.
14. Jordan Montgomery, LHP, Diamondbacks
Jordan Montgomery signed in late March, reported to the Diamondbacks’ facility out of shape and never hit his stride this year. He had such a disastrous season that Arizona owner Ken Kendrick took the blame for the signing and called it the “biggest mistake” of Diamondbacks’ season. Montgomery had been one of the more consistent starters in baseball over the previous three years, but he fell apart in 2024, posting a 6.34 ERA, 1.650 WHIP and -1.4 WAR. He exercised his $22.5 million player option after the season. The Diamondbacks will try to trade him this offseason, knowing they’ll probably have to pay down his salary by about $10 million to $12 million to find a taker, but in that range, there’s a chance a team will bite. If not, Arizona could look to move Montgomery at the beginning of next season if he pitches well.
15. Mike Yastrzemski, OF, Giants
As mentioned, the Giants will look to upgrade from platoon types to more everyday position players. Yastrzemski slashed .231/.302/.437 (110 OPS+) last season with 18 home runs and 57 RBIs over 140 games and 474 plate appearances. He’s hit 15 or more homers in four straight seasons but his best role is as a fourth or fifth outfielder. I’d love to see the Giants trade Yastrzemski to Boston, where his grandfather was a Hall of Famer. He’d be a solid 25th or 26th player for the Red Sox.
(Top image: Vladimir Guerrero Jr.: Sam Hodde / Getty Images; Garrett Crochet: Jeff Curry / Imagn Images)
