MLB Winter Meetings 2014: Dates, Schedule, Rumors and Predictions

Expect the unexpected.

There are no truer words to live by during the annual baseball winter meetings. The 113th meeting of MLB executives will take place this week in San Diego. Anything can happen when representatives from all 30 teams get together in one place.

Not every move that happens comes without warning. We'll likely get some sort of resolution when it comes to free-agent ace Jon Lester, while some trades involving heavily shopped players will likely come to fruition.

But then there are the blockbusters that nobody can predict. A casual conversation between general managers can lead to something that shakes up the entire landscape of the respective teams involved.

Because the winter meetings are filled with so much excitement, you'd be foolish not to stay informed about the dates, schedule of events and the hottest rumors. You can read up on all that information below.

Event	Time
Sunday, December 7
Business of Baseball Workshop	8 a.m. - 3:30 p.m.
Banquet	7 p.m. - 9 p.m.
Monday, December 8
Bob Freitas Business Seminar & Workshop Series	8:30 a.m. - 4:15 p.m.
PBEO Job Fair	9 a.m. - 6 p.m.
Opening Session	11 a.m. - Noon
Awards Luncheon	12:15 p.m. - 2:30 p.m.
Opening Night at the Baseball Trade Show*	5 p.m. - 8 p.m.
Tuesday, December 9
PBEO Job Fair	9 a.m. - 6 p.m.
Baseball Trade Show	10 a.m. - 5 p.m.
Bob Freitas Workshop Series	10:30 a.m. - 4:30 p.m.
Wednesday, December 10
PBEO Job Fair	9 a.m. - 6 p.m.
Baseball Trade Show	10 a.m. - 4 p.m.
Bob Freitas Workshop Series	10:30 a.m. - 12:30 p.m.
Closing Session	5 p.m. - 6 p.m.
Gala at Petco Park	7 p.m. - 10 p.m.
Thursday, December 11
Rule 5 Draft	9 a.m. - 11 a.m.

Rumors and Predictions

Lester Should Sign Soon

Jeff Chiu/Associated Press

The free-agent pitching market has largely been tied to the fate of one starter—Jon Lester.

The 30-year-old ace is widely considered the top starting pitcher on the market, ahead of both James Shields and Max Scherzer. As such, many teams are waiting to heavily engage Shields and Scherzer until Lester signs.

ESPN's Jayson Stark reports that several executives told him that Lester could ink a new contract during the winter meetings.

"Obviously, he’s nearing a decision," Stark writes. "So in the decade I’ve been doing this, I’ve never had such unanimous agreement on when any free agent would sign. Not only was next Wednesday the average of these picks [on when Lester would sign], it was the exact date selected by nearly half the group."

The executives Stark spoke to listed the Boston Red Sox, Chicago Cubs, Los Angeles Dodgers and the San Francisco Giants as the likeliest suitors. There's always room for a mystery team, though. That's a phrase you'll hear often during the next week.

Boston and Chicago aren't surprises here, but the interest of both National League West clubs is interesting.

The Giants already have a big-time lefty ace, and ESPN Stats & Info posted this image detailing Lester's and Madison Bumgarner's postseason success:

As the reigning World Series champs, the Giants would be adding to a position of strength by signing Lester.

That could explain why the Dodgers are involved in the bidding. Peter Gammons tweeted that they are serious in their pursuit:

The Dodgers could very well be interested in Lester, but there is also a chance they are simply attempting to drive the price up and effectively price the Giants out. The Dodgers certainly have the funds to make Lester work, especially as an insurance policy for Zack Greinke, who can opt out of his deal after the upcoming season.

The Giants and Dodgers don't necessarily need Lester. Both teams have aces in place. That could lead a team with a real need for one—the Cubs—to pony up the cash necessary to sign him.

Ryan Dempster, recently retired and hired as a member of the Cubs front office, is helping the recruitment process, according to ESPN's Jesse Rogers: "Jon and I have talked about how great it is to play here. He knows that."

With Dempster helping the recruitment process, Chicago will be the winner in the Lester sweepstakes.

Prediction: Cubs

Will Matt Kemp Be Dealt?

Mark J. Terrill/Associated Press

The Dodgers have significant depth in the outfield. Carl Crawford, Yasiel Puig, Scott Van Slyke, Andre Ethier and Matt Kemp will continue to compete for playing time until the organization makes a deal. A deal should have been made prior to last season, but it wasn't.

Now, it appears as if Kemp and Ethier are being dangled in the days leading up to the winter meetings. Stark tweeted an update on both players:

Ethier is the more attractive trade option given his contract ($53.5 million over the next three years including an $17.5 million vesting option for 2015). Kemp is owed $107 million over the next five years, for comparison.

That dollar amount isn't scaring away the San Diego Padres, as Fox Sports' Ken Rosenthal reports that the team is in discussions with Los Angeles:

San Diego has been linked to a few of the offseason's biggest bats since its season ended. Before Pablo Sandoval signed with the Red Sox, the Padres showed interest. They even held private workouts with Yasmany Tomas before he ultimately signed with the Arizona Diamondbacks. Most recently, Justin Upton is on their radar.

It's clear that the organization wants to upgrade its lackluster lineup. If the Dodgers are willing to pay some of Kemp's salary, San Diego is a fit.

Kemp isn't the player he was before signing his megadeal, however, so the Padres shouldn't be roped into giving up top prospects. Los Angeles does have some negotiating power given Kemp's strong second half. After posting an OPS of .760 prior to the All-Star break, he turned it on with an OPS of .971.

San Diego has been unsuccessful in its pursuit of top bats up to this point. Will this influence the team to be more aggressive and willing to deal top talent in exchange for someone who has largely disappointed since his near-MVP season in 2011?

Crazier things have happened. Don't be surprised if these two NL West foes strike a deal.

Prediction: Kemp is dealt to San Diego

Seattle Mariners Interested in Another Top Bat

Elise Amendola/Associated Press

The Mariners have shown a commitment to recruiting top bats in the past two offseasons. It's a smart strategy given their deep pitching staff.

Last season's top prize was Robinson Cano. Nelson Cruz was one of the top bats available this winter, and they locked him up just last week. Cruz, famous for his PED use, still earned a four-year, $58 million contract following a 40-homer campaign.

Seattle is now reportedly looking to add another bat associated with PEDs, according to CBS Sports' Jon Heyman: "The Mariners, seeking a top outfielder after bolstering their offense with DH Nelson Cruz, are talking to Melky Cabrera, who they apparently view as an ideal No. 2 hitter."

An offseason in which the Mariners add Cruz and Cabrera would be huge for the franchise. After making noticeable strides last season, adding a powerful right-handed bat and a versatile switch-hitter to the lineup would make the Mariners a playoff-worthy team.

Nothing is imminent yet, so anything can happen. Cabrera reportedly wants five years, so that's something that could hold up a potential deal.

Cano will certainly help in the recruitment process, as he and Cabrera were best friends while with the New York Yankees from 2005 to 2009.

Because Seattle has a clear need for more hitting, it could potentially go to great lengths to sign Cabrera. His contract shouldn't exceed Cruz's average annual value of $14.5 million. A five-year, $60 million contract could make sense.

Prediction: Mariners

Follow Kenny DeJohn on Twitter: @kennydejohn