Major League Baseball

Winter Meetings should offer endless intrigue, possibilities

Published Dec. 7, 2014 1:17 p.m. ET

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Ken Rosenthal

Here are 10 things to watch:

1. Jon Lester

The Red Sox probably could have signed Lester for something like five years, $110 million last spring. Now the price figures to be at least six years, $150 million.

The Cubs, Dodgers and Giants are the other teams known to be seriously pursuing Lester. A decision is expected at the meetings, and after that the other pitching dominoes — both with trades and free agents — will start to fall.

2. Trades involving pitchers

A number of pitchers entering their free-agent years are in play, including the Nationals' Jordan Zimmermann and Doug Fister, the Tigers' David Price and Rick Porcello, the Athletics' Jeff Samardzija and the Reds' Johnny Cueto, Mat Latos and Mike Leake.

Of those, Porcello, Samardzija and one or more of the Reds' pitchers are perhaps the most likely to be moved, if not at the meetings, then later. The Nats are expected to make another run at extending Zimmermann, and it seems unlikely the Tigers would trade Price unless they knew that they could re-sign free-agent righty Max Scherzer.

The Red Sox, according to sources, like Porcello, who is from New Jersey, owns a house in Vermont and might be inclined to sign with Boston long term. The much-rumored Porcello for Yoenis Cespedes swap? Probably not a fair exchange. Porcello is 26 and trending upward. Cespedes is three years older and his on-base percentage the past two seasons is .298.

3. Trades involving right-handed hitters

Three big ones are attracting heavy discussion — Cespedes, Justin Upton and Matt Kemp.

The signing of free agent Nick Markakis enables the Braves to move Upton and go with an outfield of Evan Gattis in left, B.J. Upton in center and Markakis in right.

The Braves could also trade Gattis, who has four years of control remaining as opposed to Upton's one. They then could keep Upton and collect a draft pick if they are unable to re-sign him a free agent. That, however, seems the less likely scenario.

As for Kemp, the Dodgers are not certain to move him — they are also talking to clubs about their two other high-priced outfielders, Andre Ethier and Carl Crawford.

4. The Padres

Remember the 2000 meetings in Dallas, when the Rangers signed Alex Rodriguez for $252 million? The Padres, under new GM A.J. Preller and a relatively new ownership, would love to make the same type of splash with the meetings in San Diego. Heck, they've been itching to make a splash the entire offseason.

They struck out on free-agent third baseman Pablo Sandoval with a bid reported to be in the $100 million range. They struck out on Cuban free agent Yasmany Tomas, who went to the Diamondbacks for six years, $68.5 million.

A trade for one of the right-handed bats seems the most logical play; the Padres have been talking to the Dodgers about Kemp for weeks. If the Pads land, say, Kemp or Upton, they likely will pull back from discussions on their starting pitchers and attempt to contend in 2015.

5. The Dodgers

When Andrew Friedman was Rays' GM, he routinely performed due diligence on virtually every player available, even ones that seemed unattainable. A number of other GMs follow the same practice, so it often seems like they're on everyone and no one at the same time.

Well, now Friedman is the Dodgers' new president of baseball operations, blessed with the financial resources to acquire virtually any player he wants. Agents want the Dodgers to pursue their players. Teams want the Dodgers to include money in trades.

Friedman is in an interesting spot, trying to streamline the team's bloated payroll while improving the club. How serious are the Dodgers on Lester? Which outfielder will they trade? The meetings will start to provide answers.

6. The Reds

General manager Walt Jocketty is in a difficult spot. The Reds, according to sources, want to reduce their payroll from $114 million last Opening Day to about $100 million. But Jocketty and owner Bob Castellini are too competitive to retrench completely.

So, the Reds are looking at all options — trades involving their starting pitchers and outfielder Jay Bruce as well as possible additions to fill their opening in left field.

7. The Phillies

They want to retool. But it might not happen at these meetings.

A trade of left-hander Cole Hamels is unlikely to occur until after free agents Lester, James Shields and possibly Scherzer find new teams. A trade of first baseman Ryan Howard and his massive contract is also something that might need to wait.

Shortstop Jimmy Rollins could be attractive for the Dodgers if he is willing to waive his no-trade clause. Outfielder Marlon Byrd is reasonably priced for one of the Kemp/Upton/Cespedes losers — he's earning $8 million next season with an $8 million vesting option for 2016.

8. Scott Boras

Scherzer is his big prize, and the common assumption is that Boras will hold him out until January, as he often does with his top free agents.

Boras, though, also has been known to strike in December. Three of his most stunning signings — A-Rod to the Rangers, Kevin Brown to the Dodgers, Jayson Werth to the Nationals — came at the Winter Meetings. Of course, they were all market-setting deals.

Both of Boras' big signings last offseason — Jacoby Ellsbury to the Yankees and Shin-Soo Choo to the Rangers — also came in December. Which isn't to say that Scherzer will sign at the meetings, or shortly thereafter. But it's not out of the question.

9. Remaining free-agent bats

Outfielder Melky Cabrera, thought to be attracting interest from the Mariners, Royals, Giants and other clubs, could sign at these meetings. So could third baseman Chase Headley, who has been a target of the Yankees and Giants.

After those two come off the board, the best hitters will be nearly all gone — and the conversation will turn to players such as Mike Morse, Colby Rasmus and Asdrubal Cabrera.

10. The relief market

Now that left-hander Andrew Miller has signed a four-year, $36 million contract with the Yankees, other free-agent relievers could reach agreements quickly.

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