Winter Meetings preview: What to watch for in MLB off-season's busiest week

From the ramifications of the new CBA to two superstars on the trade block to the market's biggest bat seeking a new team, here's everything you need to know for this year's Winter Meetings.

Baseball’s annual Winter Meetings kicked off on Sunday at the Gaylord National Resort and Convention Center in National Harbor, Md., and will run through Thursday, Dec. 8. Beyond the bookends of Sunday’s Today’s Game Era Committee Hall of Fame vote and Thursday’s Rule 5 draft, there’s no telling ahead of time exactly what will happen over the next five days, but here’s a quick guide as to a few things to watch for.

Teams dealing with the ramifications of the new Collective Bargaining Agreement

Last Wednesday, the owners and the Major League Baseball Players Association reached a deal on a new CBA that will govern the sport for the next five years. Beyond the simple continuation of business—as opposed to the owners locking out the players, or any other kind of work stoppage—teams are still digging into the fine print to understand how this this will affect their plans going forward, which could slow down the pace of business. Said Yankees general manager Brian Cashman on Friday: "Until we know what the facts of the CBA are and accurately assess it, I don't think we can strategize past that.... I don't want to make a misstep and move forward with assumptions that aren't accurate, so at the end of the day, we just have to wait to understand what the new world order is going to be, and do our best to adjust accordingly."

For the Yankees, Dodgers, Tigers and Red Sox—the four teams that exceeded the $189 million luxury tax threshold in 2016—that means accounting not just for the new thresholds ($195 million in 2017, then $197M in '18, $206M in '19, $208M in '20 and $210M in '21) but also for the graduated surtaxes based on how far over the threshold a team is and how high a percentage they'll pay for being a repeat offender. For example, via ESPN's Jayson Stark: "If the Dodgers don't get their 2017 payroll under $235 million, it appears as if their tax rate would rise to an astounding 92 (yes, ninety-two) percent as a third-time offender subject to a 50 percent tax plus a 42 percent ‘surtax’ for being $40 million over the threshold." For teams as diverse as the Yankees and Athletics, the new CBA also requires understanding changes to the revenue-sharing system: Oakland will see the phaseout of its $35 million annual take by 2020, and New York will no longer have to pay a 15% multiplier on its contribution.

What MLB’s new CBA means for the league and its players

Meanwhile, the Royals—who have Lorenzo Cain, Wade Davis, Jarrod Dyson, Eric Hosmer and Mike Moustakas all entering their final year under contract—and every other team with key players facing free agency after the 2017 season need to reconsider their plans. In the new deal, only players who decline qualifying offers and sign contracts guaranteeing at least $50 million will net a compensation pick after the first round, which could change the calculus as to whether to hold onto such players or deal them now. The new deal also sets a hard cap on international spending and even doubles the cost of Rule 5 picks. If you're dizzy trying to digest all of this, you're not the only one.

An Andrew McCutchen trade

It appears increasingly likely that the Pirates will deal their 30-year-old former MVP, even though he's coming off the worst year of his career, having hit .256/.336/.430 with career lows in OPS+ (103), Defensive Runs Saved (-28, the result of an unsuccessful strategy to position him shallower) and Wins Above Replacement (-0.7). Even so, a strong late-season rebound with the bat (.284/.381/.471 after July 31), a good track record and a reasonable price tag ($14 million in 2017, with a club option for $14.5 million and a $1 million buyout for '18), make him a desirable acquisition. The Pirates missed the playoffs in 2016 after three straight wild-card appearances, so the opportunity to stockpile multiple club-controlled young players in exchange is one they can't pass up, and they have top outfield prospect Austin Meadows nearly ready after splitting the season between Double and Triple A; he would take over in rightfield, with Gregory Polanco shifting to left and Starling Marte to center.

So far, the Nationals, Mariners, and Rangers have been most closely connected to McCutchen, though the Braves and Dodgers have entered the picture as well. Given McCutchen's age and dramatic falloff, there's no telling exactly what he'll fetch in return, except that it won't be Dansby Swanson, Trea Turner, Nomar Mazara or anyone else quite that prized. But whatever it is, the Pirates could pull the trigger this week.

Mets show willingness to spend by giving Yoenis Cespedes premium deal

Lots of talk about a Chris Sale trade … but perhaps no deal

With no aces available on the free-agent market and the White Sox signaling a desire to rebuild, the top focus of any team in need of frontline pitching is Sale, a five-time All-Star who will turn 28 next season and is under control for the next three years at just $39.5 million. While at least half a dozen teams have been connected to Sale as suitors, the White Sox are apparently asking so much in return that Fox Sports' Ken Rosenthal has reported that the Red Sox, Astros and Rangers are out at the current asking price.

Other connected teams have other irons in the fire. Based on other reports, the Dodgers are more focused on closing a deal with Rich Hill, the top free agent pitcher. The Braves, who again won't part with Swanson (but may consider doing moving top prospect Ozzie Albies, a shortstop who just split his age-19 season between Double and Triple A), may be more likely to land Rays ace Chris Archer. The Nationals are also in the mix for McCutchen, raising the question of whether they have the prospects to make both deals.

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An Edwin Encarnacion signing

With Yoenis Cespedes having re-signed with the Mets earlier this week, Encarnacion is the biggest bat remaining on the market; he matched his career high with 42 homers last year and led the AL with 127 RBIs, hitting .263/.357/.529 for a 133 OPS+. Agent Paul Kinzer expects him to sign during the winter meetings, but lately, he's seen his market narrow, at least with respect to his goal for a $100 million deal.

Encarnacion's old team, the Blue Jays, signed another designated hitter/first baseman, Kendrys Morales, to a three-year, $33 million deal before Encarnacion could even reject his qualifying offer. While Kinzer said a few days ago that the Jays—who offered Encarnacion a four-year, $80 million contract—"are showing Edwin the most love,” the team has also reportedly added first baseman/outfielder Steven Pearce via a two-year, $12.5 million deal on Monday morning, further clouding the situation.

Things aren't any clearer with other teams. The Red Sox, who need to replace David Ortiz, reportedly don't want to make a long-term commitment at the DH position. The Astros, who a couple of days ago were said to be close to signing Encarnacion, agreed to a one-year, $16 million deal with Carlos Beltran on Saturday. The Yankees have shown interest, but even before their addition of Matt Holliday via a one-year, $13 million deal, the new luxury tax changes don't bode well for them adding another nine-figure contract for a player in his mid-30s (Encarnacion turns 34 on Jan. 7). Via FanRag Sports' Jon Heyman, "a couple others" besides the Astros, Yankees and Blue Jays are in on EE as well, and Rosenthal has suggested that the Rangers (who lost Beltran) and Rockies could be interested.

The Reiter 50: Cespedes, Chapman lead list of MLB free agents

The closer carousel

Of the three top free-agent closers, Mark Melancon is getting the most play at the moment, with Rosenthal reporting that he's received multiple offers of four years and at least $60 million; the Giants, Nationals and perhaps one other team are in the mix. Both Aroldis Chapman and Kenley Jansen will get even bigger deals (and cost their new teams a first-round pick), though there's been less movement on either so far. The Yankees have been connected to the former (whom they traded to the Cubs in late July) and are considered the favorites to land him. The Marlins are reported to be interested in the latter, though it's difficult to envision them winning a bidding war against the Dodgers or another big-spending team.

Those three likely aren't the only closers who will be available this week (or winter). David Robertson, who saved 37 games last year and has two years and $25 million left on his contract, is among the players the White Sox are apparently willing to move. Davis, who will make $10 million in his final season before free agency, has been a highly-sought target since last summer.

More trade activity than usual

With the free-agent market so barren, expect a relatively heavy volume of trades as teams work together to find fits. Based on recent rumors, the Brewers' Ryan Braun, the Mets' Jay Bruce or Curtis Granderson, the Twins' Brian Dozer, the White Sox' Todd Frazer, the Tigers' J.D. Martinez and the Dodgers' Yasiel Puig are just some of the players who could be on the move.