Tom Verducci: This question has more to do with the market than the player, and Lance Lynn is likely to find a very good market as a second-tier starter. He fits in on so many staffs (Rangers, Phillies, Twins, Orioles, Mariners, Brewers, etc.), that Lynn’s price is likely to go up and beyond his true value. The red flags: Lynn is coming off a season with career worsts in strikeout rate, walk rate and FIP.
Jay Jaffe: Particularly if he goes to Boston, I think Hosmer stands to be the biggest overpay. Hosmer’s been worth a modest 8.6 WAR over the last three years, but the popular perception of him is inflated by those World Series appearances with the Royals, so much so that Scott Boras is talking about a $200 million deal, Even anything north of $100 million could be way out of line. With Pablo Sandoval gone and Hanley Ramriez heading into the final year of his contract (unless, of course, his 2020 option vests), the Red Sox seem due for a deal like this.
Stephanie Apstein: Jake Arrieta. He is still an excellent pitcher, but whoever gets him will be paying for past performance and getting future decline.
Jack Dickey: Mike Moustakas. He plays a premium defensive position well enough and is hitting the market at age 29 fresh off a 38-homer season. This is the kind of profile that prompts teams to open their wallets. Here’s the thing: He has a career on-base percentage of .305, and the ball was juiced in 2017. What happens if his fly balls start falling short and his defense continues to tail off with age? He’s less of a looming disaster than Hosmer, his longtime Royals teammate, but there are more teams hunting for third basemen than first basemen, which could spell a bidding war.
Jon Tayler: Eric Hosmer’s contract is going to feel too big by at least $30 or $40 million and a handful of years, even given his age and pedigree. And whichever team ends up paying Wade Davis like the All-Star closer he once was instead of the increasingly shaky reliever he looked like in the second half with the Cubs will want to keep that receipt handy. But the real winner of the desperation sweepstakes that is Winter Meetings will be Lance Lynn, who is going to reap the benefits of one of the worst and most scarce starting pitcher markets in the history of free agency by inking a deal far above his mid-rotation station.
Gabriel Baumgaertner: Don't pay relievers for more than three years (Kenley Jansen and Craig Kimbrel excluded). Wade Davis still has occasionally electric stuff, but some team will dramatically overpay him thinking that their bullpen is the next one to rule October.
Connor Grossman: Paying big money for a thirty-something center fielder that relies heavily on their legs is a risky gamble. That’s why Lorenzo Cain is a scary commitment. He deserves to get paid after collecting a career-best 175 hits last season hitting .300 on the nose. But he doesn’t hit for much power, doesn’t steal that many bases and will be turning 32 just after Opening Day.
He’s bound to sign for four or five years and it’s difficult to imagine he’ll still be a productive top-of-the-order hitter playing centerfield every day.