MLB Winter Meetings 2019: Dates, Schedule, Rumors and Predictions

Tim Daniels@TimDanielsBRFeatured ColumnistDecember 8, 2019

FILE - In this Nov. 21, 2019, file photo, baseball commissioner Rob Manfred speaks to the media at the owners meeting in Arlington, Texas. Major League Baseball is pushing a proposal to whack 42 teams _ and several entire leagues _ from its vast network of minor-league affiliates that bring the game to every corner of country. (AP Photo/LM Otero)
LM Otero/Associated Press

The 2019 baseball winter meetings kicked off Sunday as MLB executives descended on San Diego, allowing general managers face-to-face chance to discuss trades and meet with representatives for free agents.

Although the signings and trades are usually the highlights of the annual event, there's also the Rule 5 draft and a multitude of other activities throughout the week. It's a chance for people seeking their big break in the baseball industry to rub elbows with plenty of high-profile individuals.

Let's check out all of the details for the offseason showcase. That's followed by a look at some of the early rumors and speculation from the proverbial hot stove.


Key Information

Where: San Diego

When: Sunday through Thursday


Notable Events (all times Pacific)

Sunday: PBEO job fair (7 a.m.), Business of Baseball Workshop Series (8 a.m.), banquet (6:30 p.m.)

Monday: Opening session (9 a.m.), awards luncheon (12:15 p.m.)

Tuesday: Trade show (10 a.m.), presidential election (4 p.m.)

Wednesday: Closing session (4 p.m.), gala (7 p.m.)

Thursday: Rule 5 draft (9 a.m.)

Full list of events available on the winter meetings' official website.


Rumors and Predictions

New York Yankees Showing Interest in Gerrit Cole, Stephen Strasburg

The Yankees are on the fringe of championship contention, especially if they can avoid the rash of injuries they dealt with in 2019. A true ace is the one asset they lack, but it appears they're making a strong effort to change that via free agency.

Ken Rosenthal of The Athletic reported New York held sit-down meetings with Cole and Strasburg before the winter meetings, though it's far from alone in making a push to sign the elite right-handers.

The good news for the Yanks is they only need to convince one of them to don pinstripes. James Paxton was terrific in the second half of last season, and they feature plenty of rotation depth in the likes of Masahiro Tanaka, Luis Severino and Jordan Montgomery.

So the Yankees only need a commitment from one of Cole and Strasburg to potentially push themselves atop the World Series odds for next season. Right now, that honor belongs to the Houston Astros as +500 favorites (bet $100 to win $500), with the Yanks and Los Angeles Dodgers (both +600) close behind, per Caesars Sportsbook.

Since New York's front office likely reads the situation the same as most outside observers—the roster is probably a top-tier starter away from being complete—the club should go all-in on making one of the winter's top signings.

Predictions: Cole to Angels, Strasburg to Yankees


Anthony Rendon Could Sign Soon with Multiple Teams Involved

Rendon has been one of MLB's most overlooked superstars in recent years. That anonymity came to an end as he helped lead the Washington Nationals to a World Series triumph with a 1.003 OPS, three home runs and 15 runs batted in across 17 playoff games in 2019.

That postseason success, paired with another monster regular season highlighted by a career-high 34 homers, allowed him to hit free agency at the perfect time.

ESPN's Buster Olney reported the 29-year-old could become the first of the big-dollar free agents to sign amid interest from the Nationals, Dodgers and Texas Rangers. The Philadelphia Phillies are another team to watch, per Bob Nightengale of USA Today.

A battle between the Nats, Dodgers and Phillies for him could shift the balance of power in the National League. If he chooses L.A., that would make it the undisputed favorite in the senior circuit.

The Rangers are an interesting sleeper since the third baseman is a Texas native and the club is getting ready to open Globe Life Field, their new home park, in 2020. He could be the type of massive draw the front office would like to add to help attract fans after a 78-84 season.

That said, getting a taste of World Series baseball might convince Rendon to remain with a contender.

Prediction: Rendon to Phillies


Will the Boston Red Sox Trade Mookie Betts?

The idea of trading Betts would have seemed absurd one year ago. The Red Sox were coming off winning the 2018 World Series, and the outfielder had been named the 2018 AL MVP.

Boston failed to qualify for the playoffs in 2019, however, and owner John Henry made it clear in September the team wants to trim payroll for next year.

"We need to be under the [competitive balance tax]," Henry told reporters about the $208 million tax threshold. "That was something we've known for more than a year now."

In turn, Betts' name has popped up in the rumor mill.

ESPN's Jeff Passan reported a blockbuster deal involving the superstar five-tool player is "unlikely to happen," with the club first looking to move a pitcher to solve its payroll quandary.

The Red Sox must also consider the fan backlash that could arise from moving a player with Betts' ability and history with the team for purely financial reasons. It likely shifts trading him into the last-resort category, but it's still impossible to rule out at this stage of the offseason.

Prediction: Betts stays with Boston