Maybe it’s wishful thinking, but with the American League East seemingly in an arms race and everybody trying to catch up with the Los Angeles Dodgers and stop a three-peat, the Winter Meetings could finally be exciting again. Several major-market clubs are preparing for one of the busiest early-December baseball seasons in years. League insiders expect both New York franchises to set the tone of the week, while the San Francisco Giants and Houston Astros are viewed as teams that could surprise the industry with how aggressive they are once executives gather in Orlando, according to former MLB GMs Jim Bowden and Jim Duquette.
Talking on their Sunday morning MLB Network Radio show, The Front Office, they predicted a busy Winter Meetings, beginning Dec. 8 in Orlando.
The Yankees are widely viewed as the most motivated team heading into the Meetings. After an uneven 2025 season that exposed holes in their rotation, bench depth and left-handed balance, they are positioned to make multiple moves. New York needs at least one proven starter, a multi-position hitter and bullpen stability after relying heavily on inexperienced arms. Bowden said he could see them making two or three transactions during the event as they attempt to build a more flexible roster around their core stars.
Across town, the Mets are seen as a potential disruptor.
They finished 2025 with one of the thinnest rotations among contenders, and their offseason priorities reflect that reality. New York needs starting pitching more than any team entering the Meetings and has also explored adding an outfielder who controls the strike zone and a late-inning reliever. Some rival executives believe the Mets could be the most active team of the week if the pitching market breaks in their favor.
The Giants are also expected to be involved early.
San Francisco has made rotation stability a priority after back-to-back seasons defined by injuries and inconsistency. They are in the market for one or two mid-to-upper-tier starting pitchers and have been connected to multiple free-agent arms. Buster Posey has already shown how aggressive he wants to be when he pulled the trigger on a deal for Rafael Devers last season.
One of the more intriguing clubs to watch is Houston. Despite signaling they are shedding salaries, the Astros are still trying to compete and their needs are significant, including rotation depth, at least one outfield bat, and additional relief help after injuries thinned their roster in 2025. Some evaluators believe they could leave the Meetings with multiple additions.
If expectations hold, this year’s Winter Meetings could deliver something the sport hasn’t had in a while — multiple big-market clubs pushing at the same time, and a frenzy that starts long before the final day.
