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MLB Winter Meetings Preview

What to expect when you’re expecting baseball’s Winter Meetings.

MLB: Winter Meetings Jim Brown-USA TODAY Sports

Baseball’s annual Winter Meetings start Monday at the Gaylord National Resort and Convention Center in National Harbor, Maryland, which is just south of Washington, DC. Technically the convention gets underway today, but in truth, nothing really happens until Monday. Sunday night is for checking into your hotel suite.

So what are the Winter Meetings? They’re a convention put on every year by Minor League Baseball. Its main events are a job fair for people mostly looking for entry-level positions, mostly in minor league baseball, and a trade show where vendors show off their wares to teams as well as retailers and sporting goods distributors. There’s also an awards ceremony for things like “Minor League Executive of the Year” and “Trainer of the Year.”

Two pieces of baseball business is scheduled for the Winter Meetings. On Monday, the Hall of Fame Committee-Formerly-Known-As-The-Veterans-Committee will announce the new inductees from the “Today’s Game” list of candidates. You should expect former commissioner Bud Selig to be inducted. Longtime Braves executive John Schuerholz has a chance. Anyone else getting inducted would be a surprise.

The other bit of baseball business takes place on Thursday morning just before everyone leaves town, and that’s the Rule 5 draft.

Officially, that’s the Winter Meetings. But of course, that’s mostly of little interest to any of you and it’s not why it gets four days of around-the-clock coverage, both here and elsewhere. The reason why we pay attention to the Winter Meetings is that every major league team sends a full delegation of front office personnel to the convention. Every major player agent is there as well. Traditionally, this is the week when deals get done: both trades and free agent signings. In reality, there’s no reason that a deal needs to get made at the Winter Meetings that can’t be done over the phone. (No, Brad Pitt does not fly to Cleveland to try to broker a trade between the Indians and Athletics in person. Ever.)

But here at the Winter Meetings, trades really can be made between general managers sitting face-to-fact in a hotel suite over drinks. Agents (and occasionally even players themselves!) do go from suite to suite, knocking on doors and try to make a deal for their client. Sure, usually the preliminary stuff is done over the phone first, but deals do get finalized in person.

That’s why we follow the Winter Meetings so closely. It’s because we know that deals will be made here.

So what can we expect this winter?

Free Agents

This is one of the weakest free agent classes in recent memory and some free agents, like Yoenis Cespedes and Carlos Beltran, have already signed. (And Rich Hill is reportedly close to re-signing with the Dodgers as I write this.) But there are some free agents who are going to get big contracts nonetheless


The big prizes could be the three free-agent relief aces: Aroldis Chapman, Kenley Jansen and Mark Melancon. I’d expect Melancon to be the first one to come off the board (either to the Giants or remaining in Washington) and Chapman could return to the Yankees. Jansen is the big wild card. The Dodgers would like to keep him, but they may not be able and cut their payroll, as they reportedly are planning on doing.

I’d expect the Cubs to kick the tires on Jansen, but ultimately he probably goes elsewhere. Your guess is as good as mine as to where that is.

I do think the Cubs will look to sign or trade for a reliever, whether it is the much-rumored Daniel Hudson or someone else.


When Rich Hill is the top free agent pitcher, then you know it’s a weak class. Teams will probably turn to the trade market more than the free agent market. But beyond Hill, reportedly close to going back to the Dodgers, the best starters still on the market are guys like Ivan Nova and former Cub Jason Hammel. Also expect Tyson Ross to receive a lot of attention. Ross was released by the Padres because of some serious medical issues that will cause him to miss at least the first half of 2017, But he’s not far removed from being one of the better pitchers in the National League.

I doubt the Cubs will get involved here, although they will likely try to trade for a starting pitcher. Whether they can get a deal done is a different matter.


The two big names here are Ian Desmond and former Cub Dexter Fowler (although let’s be honest. No matter which team Dex plays for, he’s always going to be considered a Cub for life). The Cardinals, Giants and Blue Jays are reportedly interested in Fowler, and I’d guess the teams that don’t sign him will give Desmond a look. Carlos Gomez is waiting for teams that are still looking for an outfielder after the Winter Meetings.


The only real impact infielder in the free agent market is Justin Turner, who at age 31 has metamorphosed from a utility infielder who can’t play shortstop to an all-star third baseman. The Dodgers would like to keep Turner but again, they may not be able to. There are conflicting reports on the Cardinals interest, but he would be a nice fit in St. Louis.


These guys technically have a position, but really, they’re just hitters. Jose Bautista, Edwin Encarnacion and Mark Trumbo can all hit the ball a long way and all would be a nice pickup for American League teams looking for a DH. The Rockies are reportedly interested in Trumbo, and that would be interesting signing.


It’s impossible to know who is going to get dealt this week, but it certainly looks like the Pirates will deal Andrew McCutchen and the White Sox will trade Chris Sale. McCutchen is coming off a down year, but the Pirates can’t stand still in the NL Central and would like to open up a spot for top prospect Austin Meadows. The Nationals are reportedly most interested.

Sale’s strikeout numbers were down in 2016, but otherwise he’s been the same monster of the mound that he’s always been. The White Sox will probably see what they can get this week for him from 28 different teams and then move on to the rebuilding process. And no, I’m not bitter because the White Sox are being petty and refusing to trade him to the Cubs.

A third big name that may get dealt is Ryan Braun as the Brewers would love to trade him to kickstart their rebuilding efforts. But his contract and reputation may keep him in Milwaukee.

Teams that can be expected to be active on the trade front:

—-White Sox

Beyond Sale, the White Sox front office seems to understand that they need to start the rebuilding process. The White Sox will probably hang on to Jose Abreu, Adam Eaton and Jose Quintana. Everyone else who is post-arb eligible is likely available, including David Robertson, Todd Frazier and Brett Lawrie.


There has been a lot of talk that the Tigers also need to start over, but it remains to be seen if they can find trade partners for their big contracts like Miguel Cabrera, Ian Kinsler and Justin Verlander. Expect J.D. Martinez to be wearing a different uniform by the end of the week though.


The Nats are buyers, not sellers, and they do have the young prospects to interest teams. They’re reportedly in on both McCutchen and Sale. They’ve already picked up catcher Derek Norris from the Padres.


The Rays know that they can’t afford to wait to deal their veterans and they need a steady supply of young, cheap players coming up through their system to keep themselves above water in the AL East. Most of the speculation revolves around Chris Archer, and I’d expect the Cubs to be very interested in bringing Archer back to the organization if he comes on the market. But the Rays may hold on to Archer until the trade deadline.

Even if the Rays don’t trade Archer this week, look for them to deal at least one veteran pitcher such as Jake Odorizzi or Drew Smyly. The need for starting pitching in the majors will make Rays president Matthew Silverman very popular in Maryland.


Could the Braves be this year’s Diamondbacks? Last winter, Arizona felt they were just a couple players away from contending and made some big moves to add Zack Greinke, Shelby Miller and Jean Segura. They still only managed to win 69 games in 2016.

Atlanta is moving into a new stadium this year and wants to put a winning team on the field. They’ve already traded for Jaime Garcia and signed free agent pitchers Bartolo Colon and R.A. Dickey . Could they cash in some of the chips they’ve gotten for trading away everyone not named Freddie Freeman and go for it in 2017? Will they suffer the same fate as the Diamondbacks?


I don’t really expect the Cubs to be super-active this week, but I mention them because this is a Cubs blog. I do think Epstein, Hoyer and Associates will try to add some bullpen arms and as I wrote above, if Chris Archer becomes available, they’re interested. They’ll dangle Jorge Soler and try very hard to change the subject when other teams ask for Javier Baez and Kyle Schwarber.

It would be in their M.O. to go after Tyson Ross.

Rule 5 Draft:

The Winter Meetings end with the Rule 5 draft on Thursday, In truth, the Rule 5 draft gets way more attention than it deserves. I doubt the Cubs will make a pick in the Rule 5 draft. They may lose someone like Ryan McNeil or Jose Paulino, but even if they do, there’s a good chance the team that picks one of them ends up sending him back to the Cubs.

If you’re interested in learning the top names in the Rule 5 draft, check out Baseball America’s coverage.

In any case, we’ll cover every Cubs move this week. I’m sure you’re all hoping that Al and I are very busy over the next few days.