Tom Verducci: Giancarlo Stanton. The Marlins must move him for their entire business strategy to work.
Jay Jaffe: Josh Donaldson. I think the Blue Jays have to swallow hard and face the fact that it's time to move on from the 2015–16 nucleus, which has now lost Jose Bautista and Edward Encarnacion and just has so many other question marks, not the least of which is the trial balloon Rogers Communications just sent out about selling the team. If they can lock in Donaldson, a third-year arbitration-eligible player who made $17 million last year and will still be underpaid with a raise, via a reasonable a long-term extension, they should. But assuming they can't, he’ll fetch a significant return, as he's a better player than any available free agent hitter.
Stephanie Apstein: This offseason? Stanton. During the season, if the Orioles get off to a bad enough start, I could see them shopping Manny Machado at the deadline. He’s free-agent eligible after this season and could bring back a lot.
Jack Dickey: Stanton, for sure. But keep an eye on the Cubs’ position players, too. With John Lackey and Jake Arrieta both free agents, Chicago may seize a chance to turn one of their quasi-misfits (Javier Baez? Addison Russell? Kyle Schwarber? Ian Happ?) into a young arm.
Jon Tayler: They don’t come much bigger—literally—than Stanton, whose awkward and unnecessary time on the market should come to a close at some point in Orlando. Beyond that, there’s no team out there like last year’s White Sox, embracing a rebuild by selling off its best assets. Unless the Pirates decide to punt on Andrew McCutchen, the only trades I expect beyond Stanton are teams getting rid of bad contracts. Maybe Brian Cashman will use his Jedi mind trick to foist Jacoby Ellsbury and his awful deal on some team in need of a centerfielder.
Gabriel Baumgaertner: The Rays aren't in any position to win the AL East in 2018, but they don't need a full rebuild to be competitive. By trading Evan Longoria, Tampa Bay can recoup some excellent value for their star third basemen. If Longoria moves, the Rays can start molding a potential contender for 2019 while the trading partner gets one of the trustiest bats and best gloves in the American League.
Connor Grossman: Sticking with Giancarlo Stanton here, but it wouldn’t be a surprise if the Cubs flipped Kyle Schwarber. His future home is somewhere in the American League—far, far away from outfield.