Here are 7 can't-miss Winter Meetings predictions

December 5th, 2022

The Winter Meetings return Sunday to the place they last left, just as the Hot Stove gets hopping.

San Diego will be the scene of the 2022 Winter Meetings, same as it was when this event was last held, pre-pandemic, in 2019. That year, the Meetings were especially active, with Stephen Strasburg (Nationals) and Gerrit Cole (Yankees) agreeing to record-setting pitching contracts on consecutive days, the Angels signing Anthony Rendon and the Phillies signing Zack Wheeler, among other moves.

This winter, with Jacob deGrom now off the board in a blockbuster deal with the Rangers, we could see a similar spree of activity at the Meetings. (Let’s hope so, anyway.) So here are some attempts to guess what deals and developments might go down.

(Just to get ahead of the back-tracking I am about to unleash upon you, yes, I am the same fool who wrote these earth-shaking predictions at the onset of the offseason. And, yes, I am going to pivot away from a few of them here, because, as I warned at the time, none of those were especially likely to happen, anyway! Plus, what fun is reading the same thing twice?)

Aaron Judge will make his decision

The American League single-season home run record-holder signing what looks to be, at minimum, a $300 million contract less than a year after boldly turning down a $230 million extension offer is just the sort of whopper the Winter Meetings are made for. It sure looks probable, because Judge’s destination is a spark that can set off so much other movement in this market, and it’s not as if there are a ton of teams involved here.

So … which team will it be? Though we love our mystery teams (and it would be fun to see one swoop in late), the market for Judge has basically developed as expected -- Yankees vs. Giants. It’s going to be difficult (though not impossible) for the Giants to field an obvious contender in 2023 while still paying Judge his market value. So he’ll stay with the Yankees and become their new captain (or perhaps the title should be “Chief Justice”).

Update: The Mets did indeed land Justin Verlander, per a source: the defending AL Cy Young Award winner is said to have agreed to a two-year contract with a vesting option for a third season.

The Mets will make their post-deGrom move

And it’s going to be Justin Verlander. They did the mega short-term deal for Max Scherzer a year ago, and they’re going to do the same with another likely future Hall of Famer.

Verlander and his wife Kate Upton sold their home in Beverly Hills and bought a home in Jupiter, Fla. You think they want to criss-cross the country again to sign with the Dodgers? Nah, that’s too much hassle. Verlander will stay on the Treasure Coast for Spring Training, and his three-year deal -- while huge -- won’t crush a Mets team that also has to find a way to add power to the lineup. Yet again, he will pitch for a team that wears orange. It’s fate.

(The Astros have the pitching depth to allocate their financial resources elsewhere, and they’ve already begun to do that with the José Abreu deal.)

Jameson Taillon will sign, too

In this free-agent class, Taillon is in that next tier behind deGrom, Verlander and Carlos Rodón. Once Verlander gets his big Mets contract, there’s going to be serious sticker shock with Rodón, dragging his market out a tad.

But the Orioles -- a team ready to announce its presence in the marketplace and a team in need of more stable starting pitching -- is going to recognize that Taillon, after all the injuries and the illness, still has more in the tank -- in terms of overall performance and consistency -- than what we’ve seen, to date, and can help guide them where they’re trying to go.

Editor's note: Trea Turner has agreed to an 11-year, $300 million deal with the Phillies, according to a source. The club has not confirmed.

The Phillies will sign a shortstop

Another winter, another excellent shortstop market. Things can change -- especially once Judge makes up his mind -- but the Phillies are the team at the forefront of it right now. They know they’ll be without Bryce Harper at the start of the season, they can easily slide Bryson Stott to second to replace free agent Jean Segura, they have an owner in John Middleton who loved that taste of the World Series, and they have a president of baseball operations in Dave Dombrowski who is good at talking people into spending large amounts of money.

It's chalk to suggest Trea Turner will go to Philly, given his history with Harper, his wife being from nearby New Jersey and his desire to train in Florida. The fit just makes too much sense not to happen … and it will happen at the Winter Meetings.

But it’s going to take just a little more time for the Carlos Correa, Dansby Swanson and Xander Bogaerts contracts to come together. We’ve got time.

A team that has never picked at No. 1 will win the Draft lottery

A nice, new wrinkle to these Winter Meetings will be the first-ever lottery to decide the order of the top six picks in next year’s amateur Draft. All 18 non-playoff teams from 2022 have a shot at No. 1, with their percentage odds based on the final standings.

So who will land that coveted No. 1 pick? Look, if I were capable of telling you lottery results before they happen, I wouldn’t have to speculate on where baseball players would sign, because I’d be the one signing them.

But here’s a fun -- and certainly foolproof -- way of solving this riddle.

Just a few weeks ago, the largest lottery prize in history -- the $2.04 billion Powerball -- was won. The winning ticket was sold in Altadena, Calif. The best baseball player to hail from Altadena was left-handed pitcher Jim Merritt. And Merritt’s best season was in 1970, when he was a 20-game winner and All-Star for … drumroll please … the Cincinnati Reds!

Combine that super scientific breakdown with the fact that the Reds have decent odds of winning this lottery (13.2 percent, fourth best among the 18 participants), and it all makes sense. The Reds have never had the No. 1 overall pick, so they’re due.

The catcher trade market will begin to move

There is no reason a catching free-agent market fronted by Willson Contreras (who might not even be a full-time catcher wherever he winds up) and Christian Vázquez should hold back an interesting trade market in which the A’s (Sean Murphy) and Blue Jays (Alejandro Kirk, Danny Jansen or Gabriel Moreno) have valuable commodities to offer.

This is going to get started at the Meetings, with the Guardians completing a deal for Murphy. The two teams got far down the road in discussions last summer, and they ought to be able to finish the job now. Cleveland is reluctant to part with any of its top starting pitching prospects (Daniel Espino, Gavin Williams or Tanner Bibee) but should have enough prospect capital to get a deal done with or without one of those arms.

The rest will mostly be relievers

Andrew Chafin to the D-backs, Taylor Rogers to the Phillies, Carlos Estévez to the Cubs, David Robertson to the Rockies. That kind of stuff.

Yes, the above would still leave us with a LOT of unfinished business in this offseason, but would nevertheless qualify as one heck of a week. A Winter Meetings that was worth the wait!