Tom Verducci: The Brewers will be active in free agency at an unprecedented level. They need an established starter, which puts them in the mix for Jake Arrieta, Lance Lynn and Alex Cobb, and a second baseman, which might include Neil Walker. The Brewers never have spent more than $50 million on a free agent (Matt Garza for four years, signed four years ago).
Jay Jaffe: Jake Arrieta back to the Cubs. They couldn’t sign him to an extension when his value was at its peak, but now that he’s come back to earth a bit and been dinged up by minor injuries, I think the two sides find a way to get a deal done.
Stephanie Apstein: The Arizona Diamondbacks will sign Lorenzo Cain en route to a World Series title in 2018.
Jack Dickey: Ohtani eventually starts thinking “Why stop at baseball?”, and looks for a team that will allow him to start, DH, and run for governor. Because California has no long-term residency requirements for its gubernatorial candidates, Ohtani, once naturalized as a U.S. citizen, will immediately be able to join the scrum to succeed a term-limited Jerry Brown, should he sign with the Angels.
Jon Tayler: The free-agent market is a bust, we already have a good idea of where the two biggest available players will end up, and there are no teams ready to hold a fire sale. My bold prediction is that this year’s Winter Meetings will be busy but unsurprising, devoid of the wild twists and turns that previous years have given us.
Gabriel Baumgaertner: The Twins will make their biggest splash in recent memory by splurging on Jake Arrieta, a second starter and a marquee reliever. With enough young talent to make another playoff run in 2018, the Twins may as well spend now while the Tigers, White Sox and Royals all either begin or continue rebuilding.
Connor Grossman: This is an easy one based on the current climate of the hot stove season: Giancarlo Stanton and Shohei Ohtani will end up on the same team. That pretty much leaves the Giants and the Dodgers. Los Angeles would have to stitch together an 11th-hour deal with the Marlins to make it happen, but they have the prospects and financial backing to do so. Crazier things have happened.