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Winter Meetings forecast: 10 bold predictions

@castrovince
December 8, 2019

Unlike a year ago, when Mariners general manager Jerry Dipoto literally had to make a trade from his hospital bed in order to spice up the Winter Meetings in Las Vegas, the Hot Stove market is hopping as the baseball industry convenes in San Diego on Monday. So, we could

Unlike a year ago, when Mariners general manager Jerry Dipoto literally had to make a trade from his hospital bed in order to spice up the Winter Meetings in Las Vegas, the Hot Stove market is hopping as the baseball industry convenes in San Diego on Monday.

So, we could see the oft-romanticized-but-too-rarely-realized scenario in which there are a bevy of blockbuster deals going down within the walls of the Manchester Grand Hyatt at the 2019 Winter Meetings.

What follows is an admittedly ambitious batch of predictions for the Winter Meetings. If even a few of the deals listed here were to actually go down, it would still qualify as a busy week. If none of them happen, well, at least the fish tacos are good.

1) Stephen Strasburg will sign with the Nationals

Cole Hamels is off the board, so, barring an Adam Jones or Trevor Cahill deal, this is our best chance for a San Diego native to sign a contract while the Winter Meetings are in San Diego.

Now, if Strasburg were signing with the Padres in San Diego, that would be a true narrative delight. But Strasburg returning to the Nats is still viewed by many as a fait accompli in the industry. And while his market could obviously linger for weeks if he lets it (and he could have tons of cash thrown his way as the backup plan for whatever team misses out on Gerrit Cole), the Nats have plenty of incentive to get this done in the midst of what is now a scorching starting-pitching market.

2) Madison Bumgarner will sign with the Twins

Bumgarner’s probably coming off the board before the Winter Meetings officially begin Monday. I know what some of you are thinking. He’s got to stay in the National League, right? Bumgarner can’t willingly take the bat out of his hands, can he?

Nah, money’s going to talk. The Twins seem like they are willing to spend it on a pitcher to finish off a stellar rotation after bringing back Jake Odorizzi and Michael Pineda. And their analytically savvy staff will get the most out of Bumgarner moving forward.

3) Anthony Rendon will sign with the Dodgers

There are conflicting opinions in front offices as to whether Rendon will come off the board quickly or drag into January. I’m going with the former because of the presence of the Josh Donaldson alternative and because the Nationals, who want to know what direction to go at third base, are asking for an answer from Rendon soon after the Winter Meetings wrap. We know Rendon has already met with the Dodgers and Rangers, both of whom are clear fits for his services.

The Rangers have made Rendon the focal point of their offseason efforts, and there’s reason to suspect they’ll get their man. But I predicted the Dodgers at the start of the offseason, and while they also are in the market for an impact pitching acquisition, there’s no reason to back off that prediction now. I still think they’ll give him a record-breaking average annual value on, say, a five-year deal.

4) Josh Donaldson will sign with the Rangers

This is getting really greedy at this point, but, if I’ve got Rendon as a done deal, then it is conceivable that the other big domino at the hot corner could fall soon thereafter. Because of the DH, American League teams are in a better position to go the extra mile (by offering the extra year) to land Donaldson, and no AL team would be more motivated to land him than a Rangers club that has fallen short in the Rendon pursuit.

Of course, that will leave the Braves, whose offensive plan largely revolves around re-signing Donaldson, in a scramble. It could compel them to make a trade for Yankees third baseman Miguel Andújar or sign free agent Nicholas Castellanos for the outfield. But we’ll leave those deals for another week.

5) The Padres will trade for Willson Contreras

All the motivation lines up. The Cubs are motivated to improve their long-term outlook with a trade that brings in cost-controlled talent. The Padres are motivated to contend in 2020, because the front office has been put on notice.

General manager A.J. Preller has already done a lot of heavy lifting this winter with trades for outfielders Tommy Pham and Trent Grisham and infielder Jurickson Profar, and the bold free-agent signing of reliever Drew Pomeranz. But Contreras, who has three seasons of arbitration control remaining, would take the lineup to another level and erase the defensive catching concerns the Padres are carrying with Francisco Mejía behind the plate.

The Cubs don’t necessarily have to get a catcher in a Contreras trade, because they like Victor Caratini. But the switch-hitting Mejía would be an attractive piece and worthwhile risk here. If he doesn’t stick behind the plate, he could be a corner-outfield option. He’s under control for five more seasons and not eligible for arbitration for two more years.

History tells us the Padres have to do something at a Winter Meetings in their home city. In 2014, they traded for Matt Kemp. In 1985, they took Bip Roberts in the Rule 5 Draft. In 1963 ... they didn’t have a team yet.

OK, so that’s only two instances, but that’s good enough to guide us.

6) We will waste our time talking about Mookie Betts

As they attempt to get under the Competitive Balance Tax threshold, the Red Sox are going to try like heck to unload some payroll obligations by moving David Price (three years, $96 million remaining) or Nathan Eovaldi (three years, $51 million) in the right deal, and, of the two, Eovaldi is more likely to move. It also sure feels like Jackie Bradley Jr., who will likely make eight figures in his last round of arbitration, could go.

What will definitely happen at the Winter Meetings, though, is a lot more public Betts discussion than is necessary. His trade market is too limited by his projected arbitration salary and his proximity to free agency (next winter). The payroll goal is not so pressing that it should compel Boston to make a bad baseball trade.

(Francisco Lindor won’t get dealt at these Winter Meetings, either. Sorry, folks.)

7) Marcell Ozuna will sign with the Reds

Cincinnati smells opportunity in the National League Central, and that has already prompted it to make a big -- and surprising -- splash for Mike Moustakas as a second baseman. The work of improving this offense is not over, however.

Moustakas might have been a slightly unconventional fit, but Ozuna slides into the Reds’ outfield seamlessly, perhaps making Jesse Winker or Aristides Aquino available in a trade for pitching depth.

8) Didi Gregorius will sign with the Phillies

This is very much going chalk at this point, especially after the Phils non-tendered César Hernández and Maikel Franco. But the fit is obvious. Jean Segura can slide to second, and Gregorius’ power will pair perfectly with Citizens Bank Park. Gregorius and new Phillies manager Joe Girardi will be reunited in pinstripes. Red ones.

9) No, silly, Gerrit Cole won’t sign yet

I’m willing to speculate that up to two prominent Scott Boras clients (Rendon and Strasburg) will break precedent and come to terms quickly, but let’s not go totally crazy. Cole is seeking to break Price’s record $217 million pitching pact. The good things take time.

Then again, we can't rule out Brian Cashman leaving the Winter Meetings premises to get a California-bred pitcher to sign a record contract with the Yankees. Maybe that sounds familiar.

10) There will be so much hot Rule 5 action

With rosters expanded to 26 players for 2020, go crazy, folks, go crazy. Teams -- especially those in the midst of a rebuild -- will have greater flexibility to take chances on raw talent in the hope that something sticks. Here’s a list of some intriguing Rule 5 prospects from each team.

Anthony Castrovince has been a reporter for MLB.com since 2004. Read his columns and follow him on Twitter at @Castrovince.