MLB Winter Meetings: Five big questions heading into the busiest week of baseball's offseason

Major League Baseball's annual Winter Meetings will kick off this week, live from the Hilton Bayfront hotel in San Diego. The Winter Meetings are, essentially, an industry-wide meetup where a fair amount of business tends to get done—be it in the form of trades or free-agent signings. The meetings will, per usual, conclude on Thursday with this year's Rule 5 draft.

In advance of the meetings, we decided to provide a preview of sorts by taking a look at five questions that will dictate this week in baseball.

1. Will any of the other big dominoes fall?

Stephen Strasburg has already agreed to stay in D.C., which leaves us with Anthony Rendon and Gerrit Cole. Strasburg and Zack Wheeler have already agreed to a pact worth nine figures, which only helps Cole's market, who who might have a record contract on the table from the Yankees. 

As a reminder, Rendon's top suitors appear to be the Rangers, Phillies, and Nationals -- though industry sources indicated to CBS Sports the Nationals seem highly unlikely to retain Rendon. As for Cole, he's being pursued by, among others, the Yankees, Angels, and Dodgers. In other words, big-market powerhouses.

2. What about Donaldson or Bumgarner?

While the three mentioned above are undoubtedly the top free agents in the class, it's important to remember that there are other high-quality free agents still available, like Josh Donaldson and Madison Bumgarner. Both Donaldson and Bumgarner seem likely to find homes sooner than later. After all, Bumgarner is closer in value to Wheeler than Cole or Strasburg, which should hasten his negotiating process. Meanwhile, Donaldson should attract those who are ducking out of the Rendon sweepstakes.

3. Could the winter's first blockbuster trade happen?

This offseason could see a number of big-name players change hands through trades—be it Boston's Mookie Betts, Cleveland's Francisco Lindor or Corey Kluber, or even a member of the Cubs' core. (The Cubs, for their part, are supposedly telling free agents they can't negotiate deals until they clear salary, suggesting a trade might be imminent, if only so they can get on to other business.) Eventually, one of those teams will have to make the first move. The meetings tend to inspire trade activity because all the executives are stuck in the same building for most of a work week. As such, it's at least possible that the first big domino falls over the ensuing few days. At minimum, teams should be able to lay the groundwork for future deals.

4. Will the Astros' punishments be announced?

MLB's investigation into the Astros' sign-stealing scandal is ongoing. At some point—presumably before the season begins—commissioner Rob Manfred figures to hand down punishment in some form or another. Whether that's a fine, a suspension, draft-pick stripping, or whatever else is to be determined. The Winter Meetings would seem like the first logical occasion for Manfred and crew to divulge more about the investigation and/or the forthcoming punishments. 

5. Who are the names to know in the Rule 5 draft?

We'll have a full Rule 5 draft preview later in the week. For now, we'll note that some of the names worth knowing include Rangers reliever Joe Barlow, Braves reliever Thomas Burrows, Twins starter Griffin Jax, and Mets shortstop Shervyen Newton. Again, we'll have more on those players (and others) soon.

CBS Sports Staff

R.J. Anderson joined CBS Sports in 2016. He previously wrote for Baseball Prospectus, where he contributed to five of the New York Times bestselling annuals. His work has also appeared in Newsweek and... Full Bio

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