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This conversation may or may not involve the Chris Sale trade.
This conversation may or may not involve the Chris Sale trade.Michael Ivins/Boston Red Sox/Getty Images

Biggest Winners and Losers of the 2016 MLB Winter Meetings

Zachary D. RymerDec 8, 2016

The party in National Harbor, Maryland, is over. Major League Baseball's winter meetings have come and gone, leaving us to pick up the pieces.

Tell you one thing: It's not hard to see who made out well and who didn't.

Let's get into that by looking at the six winners and four losers of the winter meetings. They're a nice balance of teams and individual players who are walking away from Gaylord National Resort and Convention Center with either smiles or scowls.

We'll go in no particular order, but we'll start by assessing by far the biggest move of the week...

Winner: Boston Red Sox

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Leave it to Dave Dombrowski, Master of the Blockbuster, to pull off the biggest trade of the week.

The Boston Red Sox's president of baseball operations added another doozy to his collection when he acquired Chris Sale from the Chicago White Sox on Tuesday. A starting rotation that already had reigning American League Cy Young winner Rick Porcello and former Cy Young winner David Price now has a left-hander who's finished in the top six of the Cy Young voting five seasons in a row.

Overkill? Maybe a little bit.

"Pretty much Sale or nothing," Dombrowski said of his approach to his rotation this winter, per Ian Browne of MLB.com. "We didn't have any other conversations taking place because we like our rotation as it is. I really didn't think it was a big need for us." 

However, there's no rule that says teams must only use the offseason to patch holes. They can also make strengths even stronger. That's what the Sale trade does for the Red Sox. They now have arguably the American League's best rotation, not to mention one that could own a short postseason series.

Besides, adding Sale didn't stop Dombrowski from conducting other business.

He also acquired reliever Tyler Thornburg, who's fresh off a 2.15 ERA, from the Milwaukee Brewers. Mitch Moreland, a Gold Glove winner with pop, signed to a one-year deal to pad the club's first base and designated hitter depth.

After Boston's 93 wins and AL East title in 2016, FanGraphs' projections have the Red Sox entrenched as the team to beat in the American League in 2017. Anyone care to argue?

Winner: Chicago White Sox

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The Red Sox made out well in the Sale trade, but the White Sox also did well in that deal and another.

Absent from the previous slide is the price the Red Sox paid to pry Sale from Chicago. It included four prospects, headlined by infielder Yoan Moncada and rounded out by right-handers Michael Kopech and Victor Diaz and outfielder Luis Alexander Basabe.

As I covered more extensively Tuesday, Moncada is as good a centerpiece as the White Sox could have asked for. The 21-year-old Cuba native is a bundle of power and speed who's torn up the minor leagues en route to the top overall spot in assorted prospect rankings, including MLB.com's.

"I'm not going to put any big league names on him in terms of who he's similar to, but a little Google search will show you who he is compared to," said White Sox general manager Rick Hahn, per Scott Merkin of MLB.com. "We shared that kind of view of his future. That was an important piece."

Kopech is emerging as one of the top power arms in the minors and is No. 3 in MLB.com's rankings of the White Sox's prospects. Basabe (No. 9) also ranks among their best.

A day later, Hahn pulled off a similar score when he traded outfielder Adam Eaton to the Washington Nationals. That brought back right-handers Lucas Giolito, Reynaldo Lopez and Dane Dunning. Giolito and Lopez are elite pitching prospects, and Dunning is good enough to crack Chicago's top 10.

The White Sox may not be done trading. They still have Jose Quintana, Todd Frazier, Jose Abreu, David Robertson and Melky Cabrera to run up the ol' flag pole. 

But even as things stand, they've done enough. Jonathan Mayo of MLB.com wrote there's "no question" the White Sox now have a top-10 farm system.

Loser: Pittsburgh Pirates

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So much for the seemingly inevitable Andrew McCutchen blockbuster we heard so much about going into the winter meetings. Nothing happened, and nothing's likely to happen.

The Nationals probably won't take McCutchen. Today's Knuckleball's Jon Heyman reported the Nats were focused on swinging a deal for the veteran center fielder after missing out on the Sale sweepstakes. But then came the Eaton trade. 

Another possibility for McCutchen was the Texas Rangers. Ken Rosenthal of Fox Sports reported Monday that they were in "frequent contact" with the Pirates. 

Instead, the Rangers brought back Carlos Gomez on a one-year contract. With him set to play center field every day, that's another fit for McCutchen off the board.

That leaves...who, exactly?

Buster Olney of ESPN.com mentioned the Los Angeles Dodgers, but Joc Pederson's presence gives them little incentive to meet a high asking price for the former MVP. Jon Morosi of MLB Network mentioned the Seattle Mariners, but they're short on the impact talent it would take to acquire McCutchen.

With no clear suitors left in play, it's damage-control time for the Pirates and McCutchen.

General manager Neal Huntington told Travis Sawchik of the Pittsburgh Tribune-Review that the team is looking forward to having McCutchen in the lineup in 2017. For his part, the outfielder is engaging in cryptic, seemingly passive-aggressive tweeting.

Suffice it to say things are awkward. That's never a fun platform from which to move forward.

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Loser: New York Yankees

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Good job, New York Yankees. You just dropped a record contract on a guy you don't need.

The contract in question is the five-year, $86 million deal the Yankees gave lefty closer Aroldis Chapman on Wednesday, per Bryan Hoch of MLB.com. That's $24 million more than the San Francisco Giants gave Mark Melancon.

This pact is somewhat defensible. Chapman has done nothing but dominate since 2012, compiling a 1.84 ERA and using his triple-digit heat to strike out 15.7 batters per nine innings. And as Yankees general manager Brian Cashman pointed out, he only costs money.

"There's an attractiveness to his availability in the marketplace because he didn't have a draft pick attached to him," he told Hoch on Thursday. 

However, there are good reasons why this deal is being panned in just about every direction you look. 

The Yankees only won 84 games in 2016. Adding a pitcher who'll only give them 60-odd innings won't boost that number much. They won't come close to the juggernaut Red Sox.

The Yankees' hopes rest more on their robust collection of young talent, which is likely a couple of years away from maturing into a backbone for a contender. By then, the soon-to-be 29-year-old Chapman may no longer have the fastball that's made him famous. 

There's also no ignoring the public-relations aspect of this deal. The Yankees pride themselves on being classy, yet here they are handing a truckload of money to a guy who was suspended 30 games in 2016 for an alleged domestic violence incident. This will leave a bad taste in the mouths of some fans.

This doesn't feel like the Yankees are spending money because they should. It feels like they're spending money because they can.

Winner: Rich Hill

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We all love a good comeback story. Rich Hill's continues to be the best baseball has going.

The most recent chapter came Monday. In a deal that didn't exactly come out of nowhere, Hill re-signed with the Los Angeles Dodgers for three years and $48 million.

This is far from the biggest contract ever given to a starting pitcher. Heck, it even pales in comparison to what the best relievers are getting on this winter's market.

And yet it's a fitting reward for Hill after all he's been through. After a promising breakthrough with the Chicago Cubs in the mid-2000s, he boarded a roller-coaster ride beset by injuries, ineffectiveness and accompanying job instability. Off the field, Hill's newborn son died in 2014.

Hill reached his low point on the field when he signed with the independent Long Island Ducks in the summer of 2015. Or, so it seemed. It was the start of a reinvention process that carried him to a 2.00 ERA across 24 major league starts in 2015 and 2016.

This made Hill, now 36, the best pitcher available on the open market. And now he has a contract worth more than five times his career earnings to date.

"It's been an incredible journey, but I never felt like packing it all in. You fail, you learn. When you fail, you learn," he said, per Ken Gurnick of MLB.com. "I don't think you really know what failure is—or I didn't know what failure was until I got older and understood that that was experience. Baseball teaches us to deal with things off the field that are far greater than what you deal with on the field."

Everyone, give the guy a hand.

Winner: Ian Desmond

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Two years ago, Ian Desmond gambled on himself and lost. He's since made up for that.

The two-time All-Star found a new home Wednesday, signing with the Colorado Rockies for five years and $70 million. The deal also includes a sixth-year option for $15 million.

This puts Desmond in a very different spot from the one he was in last winter.

He was reeling from a disastrous 2015 season that included a .674 OPS and bad defense at shortstop. That may have been the result of pressure he put on himself after rejecting a nine-figure contract offer from the Washington Nationals in 2013.

The offseason market forced Desmond to settle for a one-year, $8 million deal with the Texas Rangers. He promptly rebuilt his value with an All-Star season highlighted by a .782 OPS, 22 home runs and 21 stolen bases. He also made a smooth transition from shortstop to the outfield.

Between the money he made in 2016 and the money he could make in his deal with the Rockies, Desmond has avoided the ultimate catastrophe from rejecting that nine-figure offer. It would have bought out five free-agent years at $89.5 million. He could make $93 million between 2016 and 2022.

Not quite tit for tat, but it's close enough to end discussions about what might have been for Desmond.

Loser: Colorado Rockies

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To Ian Desmond I say, "Well done." To the Rockies I say, "Is your head on straight?"

It's one thing that the Rockies may have reached a little too far in giving Desmond $70 million. That's more than MLB Trade Rumors and Jon Heyman projected he would get.

It's another thing that the Rockies gave up a draft pick to sign Desmond. This is even worse, as for them that meant sacrificing the No. 11 selection in the 2017 draft. Per Matthew Murphy's 2014 article for The Hardball Times, that pick carries a net value of over $20 million.

This would be easier swallow if the Rockies were in win-now mode. But after Colorado won 75 games in 2016, it's only projected to win 79 in 2017, per FanGraphs. Desmond does lengthen out an already formidable lineup, but the most you can say about the team is that it's interesting.

Then there's the matter of Desmond's role.

Rather than at shortstop or in the outfield, Ken Rosenthal reports the Rockies are eyeing Desmond for first base. He's never played there before, nor does he profile well at the not-so-hot corner. It will waste his excellent throwing arm and isn't a good place to stash his good-not-great bat.

The perception of this deal can change if the Rockies use their outfield depth to acquire an arm that could help put them over the edge. But for now, this doesn't look like money well spent.

Loser: Edwin Encarnacion

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Anybody want Edwin Encarnacion? Anyone? Bueller?

Welcome to Encarnacion's offseason nightmare, in which he's bouncing from one rejection to the next. It started with one of his own when, as Jon Heyman reported, he passed on an $80 million offer to remain with the Toronto Blue Jays. Since then, it's been other teams doing the passing.

The Blue Jays have moved on, signing Kendrys Morales and Steve Pearce. The Houston Astros went for Carlos Beltran to fill their slugger need. The Yankees went for Matt Holliday. Despite David Ortiz's blessing, the Red Sox effectively said no to Encarnacion when they signed Mitch Moreland. The Rockies may have been able to afford him but opted for Desmond instead.

That's a lot of potential suitors off the board, and Encarnacion's market started feeling the effects during the winter meetings. According to Jeff Passan of Yahoo Sports, no team will even do three years and $60 million at this juncture.

This raises the question of whether Encarnacion overplayed his hand. The thing to keep in mind is that such questions are often answered in the negative. That could be the case here, too.

"Teams shouldn't overplay their hands with him, either. He's too good for the price to go much lower," one GM told Passan.

But with so many doors now closed to Encarnacion, it's also fair to wonder how high he can go. He set off thinking he could at least do better than $80 million. That may now be a fool's hope.

Winner: San Francisco Giants

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We discussed a team that paid too much money for a closer it didn't need. Now we discuss the opposite.

Oh, sure. The Giants didn't sign Mark Melancon for nothing Monday. At the time, it was his four-year, $62 million contract that was the new standard-bearer for relief pitchers. It easily topped the $50 million Jonathan Papelbon got from the Philadelphia Phillies in 2011.

But after Aroldis Chapman took the bar and raised it up above the clouds, suddenly $62 million for Melancon doesn't sound so outrageous.

He's been just as good as Chapman in recent years, after all. Melancon's 1.80 ERA since 2013 is the best of any relief pitcher, and it comes with a sparkling 5.96 strikeout-to-walk rate. And since he does this with movement and location rather than velocity, the 31-year-old may avoid the usual effects of aging.

And boy, did the Giants need Melancon.

They only won 87 games and settled for a wild-card spot in 2016. But looking back, that feels like a small miracle given what their bullpen did to them. Giants relievers blew a league-high 30 saves and were about as reliable as a tissue paper flak jacket by the end of the year.

"It gives the club peace of mind, with so many close games that we play, that we have a lockdown guy for the ninth inning," Giants general manager Bobby Evans said, per Chris Haft of MLB.com.

With plenty of talent elsewhere, Melancon is a finishing touch for the team. Look for it to contend in an odd year for once.

Winner: Chicago Cubs

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The Chicago Cubs also needed to find a closer this winter. They could have easily re-signed Aroldis Chapman or gone for Mark Melancon or Kenley Jansen.

But why spend that much money when you can skip the free-agent market for something just as good?

That's what they did in trading for Kansas City Royals closer Wade Davis on Wednesday. All he's done since 2014 is compile a 1.18 ERA and hold hitters to a .456 OPS. That's not counting his postseason work, in which he's allowed one earned run in 25 innings.

The right-hander does come with health questions after forearm trouble limited him to 45 appearances in 2016. But the Cubs aren't too worried about that.

"[Davis] had a terrific September, and we watched every outing and he looked really good," general manager Jed Hoyer said, per Carrie Muskat of MLB.com. "We felt really comfortable with the [medical] file and the examination and the way he threw in September."

The $10 million the Cubs owe Davis for 2017 isn't cheap, but it's fine relative to the going rate for elite relief pitching on the open market. And in giving up Jorge Soler to get him, the Cubs didn't part with a piece they're likely to miss. The powerful right fielder was an odd man out in their outfield.

So, what we have here is a team that just won 103 games and the World Series making a smart move for a top-notch relief pitcher. It's almost as if they like winning so much they figure they'll keep trying it.

Stats courtesy of Baseball-Reference.com and FanGraphs unless otherwise noted/linked.

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