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A Justin Upton trade would seem to be inevitable.
A Justin Upton trade would seem to be inevitable.Al Behrman/Associated Press

10 Impact Deals to Watch for During MLB Winter Meetings

Zachary D. RymerDec 5, 2014

Put a whole bunch of Major League Baseball executives and player agents in one place for a few days, and there's bound to be action.

Yup, it's time to start looking forward to the winter meetings. The offseason has already produced its share of impact trades and free-agent signings, and there ought to be a few more in San Diego next week.

Naturally, that's our cue to see if we can predict some of them.

Ahead of you are 10 impact deals that could be pulled off next week. Note that "during" is the key word here, as a few deals are more likely to happen after or before the winter meetings.

For example, Max Scherzer is probably going to sign well after the winter meetings, while there's strong speculation that Andrew Miller and Jon Lester could sign before. Assuming they do, the fallout of their signings is a good place to start the predictions...

Signing: Francisco Liriano to the Boston Red Sox

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With Jon Heyman of CBSSports.com reporting the Chicago Cubs have the high offer out to Jon Lester and Rob Bradford and Alex Speier of WEEI.com reporting the Los Angeles Dodgers are making a charge, it's a safe bet that the Boston Red Sox aren't signing Lester again.

If they are indeed forced to turn to other options for rebuilding their starting rotation, it wouldn't be the least bit surprising if the first guy on their list is Francisco Liriano.

In early October, Peter Abraham of The Boston Globe wrote that the Red Sox "seem infatuated" with the 31-year-old lefty. Rightfully so. Liriano may come with control issues, but his time in Pittsburgh has turned him into a strikeout pitcher (9.4 K/9) who keeps the ball on the ground (52.4 GB%, per FanGraphs).

To boot, Liriano's cost wouldn't be outrageous. He's tied to draft-pick compensation, but Boston's first-round pick is protected. And if a report from Bill Brink of the Pittsburgh Post-Gazette about Liriano only wanting $12 million per year over three or four years is accurate, the Red Sox can definitely afford that.

The Red Sox's signing of Liriano would be a solid start, but they'd need more after missing out on Lester. Don't be surprised if another move at the winter meetings sees them trade for...

Trade: Jeff Samardzija to the Boston Red Sox

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...Jeff Samardzija.

The trade of Josh Donaldson made it clear enough that Oakland A's general manager Billy Beane is in a selling mood, and Samardzija is now his best trade chip. Ken Rosenthal of FoxSports.com figures he'll be dealt sooner rather than later, and Nick Cafardo of The Boston Globe says the Red Sox are in on him.

If so, that's not surprising. The 29-year-old right-hander is not unlike Liriano in that he's a strikeout pitcher (8.8 K/9 since 2012) who keeps the ball on the ground (50.2 GB% in 2014, per FanGraphs), and his control has drastically improved as he's gained experience as a starter.

One catch with Samardzija is that he's due for free agency after 2015, but that makes him relatively affordable in a trade. The A's could go for on-base machine Daniel Nava, spare center fielder Jackie Bradley Jr. and/or top prospect Deven Marrero, who's blocked by Pablo Sandoval and Xander Bogaerts.

If a trade for Samardzija and a deal for Liriano are worked out, the Red Sox will have responded well to losing Lester. Another team that will likely be looking to respond to missing out on Lester, meanwhile, is...

Signing: Chase Headley to the San Francisco Giants

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...the San Francisco Giants.

If the Giants miss out on Lester after also failing to re-sign Sandoval, they'll be looking for other ways to spend a whole bunch of available money. Here's thinking that could lead them to Chase Headley.

Giants assistant GM Bobby Evans confirmed to Henry Schulman of the San Francisco Chronicle that the team is in on the 30-year-old third baseman, and understandably so. He would fill Sandoval's shoes at third and arguably be an upgrade.

Though Headley isn't the standout hitter he teased himself as in 2012, he's at least above-average. He's also a solid baserunner for a corner infielder and an elite defender at third. With this kind of skill set, it's no surprise WAR favors him over Sandoval the last two years, per FanGraphs.

Headley won't come cheap, but the Giants can definitely afford him if they were prepared to spend $100 million or so on either Sandoval or Lester. Headley might go for half that much.

The Red Sox signing Liriano and trading for Samardzija and the Giants signing Headley would do it for the fallout from Lester signing before the winter meetings. As for the fallout from Andrew Miller signing early, look for fellow relief ace David Robertson to end up with...

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Signing: David Robertson to the Toronto Blue Jays

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...the Toronto Blue Jays.

Robertson was last seen closing games for the New York Yankees, but there's a lot of sense to the Yankees being heavily involved with Miller, according to Jon Heyman. Signing him while letting Robertson go could mean a discount and, if Robertson were to leave, a much-needed draft pick.

So let's assume the Yankees sign Miller. That would leave Robertson looking for a new home, and that's when the Blue Jays could ramp up the interest that Heyman says they have in him.

With Casey Janssen gone, the Blue Jays need a closer. Signing Robertson would be a massive upgrade in that regard, as his production dwarfed Janssen's in virtually every category in 2014.

The 29-year-old right-hander would cost a lot, but it helps that the Jays just saved a few million bucks in swapping J.A. Happ for Michael Saunders. And while signing Robertson would require surrendering a draft pick, the Jays already surrendered their first-rounder when they signed Russell Martin.

If the Jays do sign Robertson, it would all but be official that they're moving on from Melky Cabrera. But that's OK, because there's another possible home for him in the AL East with...

Signing: Melky Cabrera to the Baltimore Orioles

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...the Baltimore Orioles.

You've probably noticed that the Orioles have been hit hard by free agency. First, they lost a bunch of right-handed power when Nelson Cruz signed with the Seattle Mariners, and then they lost a steady right fielder and top-of-the-lineup presence when Nick Markakis signed with the Atlanta Braves.

That the Orioles made attempts to keep both Cruz and Markakis suggests they have some money to spend. Given that they now have one massive hole in their outfield and two holes in their lineup, they're candidates to pick up one of the outfield bats still available.

And that basically means Cabrera.

The 30-year-old switch-hitter wouldn't be a natural fit as a replacement for Markakis, but he'd be a needed upgrade in left field. His bat, meanwhile, would definitely be an upgrade over Markakis'. Cabrera is a .309 hitter since 2011, with solid power to boot.

If Cabrera signs with Baltimore, it's Nori Aoki who would stand out as the best top-of-the-order hitter available. And you could look for him to sign with...

Signing: Nori Aoki to the Detroit Tigers

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...the Detroit Tigers.

Aoki ending up in Detroit is an idea Ben Reiter of Sports Illustrated proposed at the start of the winter: "The Tigers' outfielders, as a group, were among the league's worst fielding units, and they could generally stand to get a bit more athletic and, for lack of a better word, pesky. Aoki would amount to a peskiness infusion."

With Torii Hunter having left for the Minnesota Twins, we now know that Aoki would fill a hole in right field. His defense would indeed be an upgrade over the statuesque defense that Hunter played in 2014, and his contact-oriented style would be a welcome addition to the top of Detroit's batting order.

Aoki also shouldn't be too expensive. That's good news for a Tigers team that's loaded with big contracts and already committed to $125 million worth of guaranteed money in 2015.

With Cabrera and Aoki off the market, the most intriguing outfielder still available would be Colby Rasmus. Don't be surprised if he ends up with...

Signing: Colby Rasmus to the San Diego Padres

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...the San Diego Padres. 

I'm going out on a limb with this one, as there hasn't been much buzz (if any, really) linking Rasmus to San Diego. But we do know the Padres had the worst offense in baseball by a mile in 2014, and we also know from ESPN's Buster Olney that new GM A.J. Preller is aggressively seeking hitters.

Rasmus is one of the more powerful center fielders around, and the Padres are coming off a season in which they got just a .334 slugging percentage out of center field. He also shouldn't be too frightened of Petco Park, as it was a solid haven for lefty power hitters in 2014.

Also of note is that Rasmus is affordable, as he's a classic candidate for a one-year pillow contract. Giving him one of those would be a way for Preller to show he's at least making an effort, and the contract could easily be moved over the summer if San Diego's 2015 season were to go south.

Mind you, it's a good bet the Padres wouldn't be done even if they do add Rasmus. They'd still need offense, and they could get some by dealing for...

Trade: Yoenis Cespedes to the San Diego Padres

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...Yoenis Cespedes.

While Rasmus makes sense for the Padres, the word from Corey Brock of MLB.com is that San Diego's main focus is on the trade market. That's where they are "believed" to have discussed Cespedes with the Red Sox, and they definitely have the pieces to get him.

The one thing the Padres have to deal is the one thing the Red Sox will still need even if they acquire Liriano and Samardzija: pitching. Brock suggested Ian Kennedy as a possible option, and I wrote the other day why he might be the most sensible trade target linked to Cespedes so far.

Kennedy would give the Red Sox a solid innings-eater at worst and a strikeout-happy No. 2 at best. For the Padres, Cespedes would be another power bat to pair with Rasmus and Jedd Gyorko.

And since Cespedes is a free agent after 2015, he, like Rasmus, could also be moved over the summer if San Diego's season were to go south.

If Cespedes is traded, the most attainable right-handed power bat on the trade market would be the one belonging to Justin Upton. Look for him to end up with...

Trade: Justin Upton to the Seattle Mariners

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...the Seattle Mariners.

Braves boss John Hart told Jim Duquette of MLB Network Radio that it's "not out of the realm of possibility" Upton will be extended before he hits free agency after 2015, but his cost is likely beyond Atlanta's grasp. It's more likely Hart will get what he can for Upton like he did with Jason Heyward.

It's also noteworthy that Upton is a bit more expendable now that the Braves have Markakis. As for the Mariners, they need a right fielder now that Saunders is gone and just added Happ to their rotation, which may not leave room for Taijuan Walker. As Dave Cameron of FanGraphs opined, "Those two things seem related."

Indeed, and this wouldn't be the first time Seattle dangled Walker for Upton. He was to be the centerpiece of a deal between the Mariners and Arizona Diamondbacks a couple of winters ago that Upton shot down.

The Braves, meanwhile, should be interested in a swap for Walker. The 22-year-old right-hander's upside is through the roof, and he's controllable through 2020. He would give the Braves a potential ace to control for years, and the Mariners would get a right fielder who would complete a dangerous lineup.

If it happens, though, the Braves would be signing up for a potentially rocky 2015. That could be the Miami Marlins' cue to get aggressive and go after...

Trade: Brandon Moss to the Miami Marlins

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...Brandon Moss.

The left-handed slugger is yet another valuable trade chip at Beane's disposal, and ESPN's Jayson Stark has heard from one executive that he is "going to trade Brandon Moss."

John Hickey of the Bay Area News Group says the Cleveland Indians are interested, but the Marlins need him more. Joe Frisario of MLB.com wrote in late November that the Marlins want a slugger to pair with Giancarlo Stanton and listed Moss as a potential fit.

The lefty-swinging Moss, who has 76 home runs since 2012, would be a fine complement for Stanton. He'd also be an easy upgrade at first base over Garrett Jones, who had just a .720 OPS in 2014.

The Marlins also work pretty well as a trade partner for the A's. A guy like Brad Hand fits the mold of pitcher the A's tend to prefer, and Derek Dietrich is controllable property who has power the A's could use at second base.

At any rate, that'll do it for my predictions. Maybe all of them will come true. Maybe only some will. Maybe none will.

But one way or another, I guarantee you this: We're going to have a lot to talk about next week.

Note: Stats courtesy of Baseball-Reference.com unless otherwise noted/linked. Contract and payroll information courtesy of Cot's Baseball Contracts.

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