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Ranking the 5 Best Impact Moves of the MLB Offseason Thus Far

Jacob ShaferDec 21, 2014

The 2014 MLB offseason isn't over yet. We've still got another two months to slog through; more big-time contracts will be inked, and major trades will be consummated.

Still, we've cleared several significant hurdles, including the winter meetings, which means we can begin to take stock of where things stand.

With that in mind, here are the top five moves made so far—be they trades or free-agent signings—ranked according to how much they benefited the receiving team and who got the best deal and/or bargain.

Surely there's more moving and shaking on the horizon. For now, this is the stuff that has made the long, cold winter a little more tolerable—and made the hot stove crackle. 

Pittsburgh Pirates Re-Sign Francisco Liriano

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Before many of the big pitching dominoes fell, Francisco Liriano re-upped with the Pittsburgh Pirates for three years and $39 million, per CBSSports.com's Jon Heyman.

On the surface, it might seem like a secondary deal, but the 31-year-old Liriano, who posted a 3.38 ERA with 175 strikeouts in 162.1 innings last season, was among the more coveted arms on the market this offseason.

More than that, his signing signals a philosophical shift for the spendthrift Pirates.

According to Travis Sawchik of the Pittsburgh-Tribune Review, the Liriano contract is the largest in franchise history for a free agent and "should build some goodwill" with fans.

Most of all, it'll help Pittsburgh push toward a third straight postseason appearance (assuming Liriano stays healthy).

Los Angeles Dodgers Acquire Howie Kendrick

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After a quiet start to the offseason, the Los Angeles Dodgers have established themselves as legitimate players.

No move embodies general manager Andrew Friedman's philosophy more than the series of swaps that essentially exchanged Dee Gordon for Howie Kendrick.

Oh, it was more complicated than that. First, Los Angeles dealt Gordon to the Miami Marlins in a package that also included veteran pitcher Dan Haren and netted top Marlins pitching prospect Andrew Heaney.

Almost immediately, LA sent Heaney to the Los Angeles Angels for Kendrick.

In essence, the Dodgers turned second baseman Gordon and his 3.1 WAR into Kendrick and his 4.6 WAR, per FanGraphs

Of course, that's discounting the value of Heaney, who Steve Dilbeck of the Los Angeles Times thinks "could become a mainstay in the Angels rotation, if not next season, soon."

Meanwhile, Dilbeck notes, Kendrick has only one more year left on his contract. 

“There are a lot of different ways it can play out, but we’re excited to have him," Friedman told Dilbeck. "All of our focus right now is on the 2015 season. Assuming that things play out well and Howie likes it here, I’m sure those conversations will happen at some point."

Translation: Assuming he's the upgrade we think he is, we'll keep him around.

New York Yankees Re-Sign Chase Headley

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When the New York Yankees inked their incumbent third baseman to a four-year, $52 million pact, per Jon Heyman of CBS Sports, it was that rare animal in the Bronx: a (relative) bargain.

Headley posted a mediocre .229/.296/.355 slash line in 77 games with the San Diego Padres last year. But after a trade to New York and away from cavernous Petco Park, he hit .262 with six home runs and 17 RBI in 58 contests.

The 30-year-old switch-hitter won't likely repeat his 2012 campaign, when he bashed 31 home runs, drove in 115 and finished fifth in the MVP voting. But there's reason to assume his bat will benefit from a full season at Yankee Stadium.

There's also Headley's superlative defense. He won a Gold Glove in 2012, and the advanced statistics like him, too: His 28 Ultimate Zone Rating (UZR) was tops among all MLB position players in 2014, per FanGraphs

Compare Headley's contract to the one the Boston Red Sox handed Pablo Sandoval. Yes, Sandoval is two years younger than Headley, but he hit just three more home runs last season and finished with a slightly lower OBP, and don't forget Headley has the edge with the leather.

Yet Sandoval got five years and $95 million from Boston with a $17 million club option for a sixth year and a $5 million buyout (the buyout is factored into the $95 million total), per Alex Speier of WEEI.com. 

That's $95 million in guaranteed greenbacks, or nearly double the amount New York spent on Headley. Waistline aside, is Sandoval double the player?

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Chicago Cubs Sign Jon Lester

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Jon Lester was the prized catch in a deep free-agent sea, and he motivated numerous clubs to cast their lines.

Right up to the end, the Boston Red Sox, San Francisco Giants and Chicago Cubs were in on the 30-year-old left-hander, with the Dodgers also supposedly in the mix.

Finally, Lester elected to go with the Cubs. The six-year, $155 million deal, first detailed by Jon Heyman of CBSSports.com, may seem huge...and it is.

But Lester's track record speaks for itself. The southpaw posted a 2.46 ERA and 1.102 WHIP in 219.2 innings with the A's and Boston Red Sox last year.

He's also a playoff-tested stud who owns a 2.57 ERA in 84 postseason innings, along with a pair of rings.

That last bit is especially important to the Cubs, who are trying to break their century-and-counting curse. President of baseball operations Theo Epstein, who was Lester's general manager in Boston, helped lure the ace to the Windy City with that lofty goal in mind.

San Diego Padres Acquire Justin Upton

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Once the forgotten club in the National League West, the San Diego Padres are suddenly a factor.

That's thanks to the aggressive wheelings and dealings of general manager A.J. Preller, who appears determined to propel the Pads back toward relevance.

The latest salvo in San Diego's war for respect was the trade that netted outfielder Justin Upton from the Atlanta Braves, per Fox Sports' Ken Rosenthal

That followed a flurry of moves that sent slugging outfielder Matt Kemp, 2013 American League Rookie of the Year Wil Myers and All-Star catcher Derek Norris to San Diego, among others.

It's all a roll of the dice, as The New York Times' Benjamin Hoffman spells out:

"

Rather than waiting to see how much better the team would be if some of his players had more typical seasons, however, A. J. Preller, San Diego’s general manager, reshaped the roster, trading a huge chunk of the farm system for Justin Upton, Matt Kemp, Wil Myers and Derek Norris.

Suddenly, a team of little-known underperformers had a group of household names with excellent credentials: five All-Star appearances, two Gold Gloves, four Silver Sluggers, a rookie of the year award and two top-10 finishes in Most Valuable Player award voting.

"

Whether the Padres will dominate a division that features the World Series champion San Francisco Giants and the free-spending Los Angeles Dodgers remains to be seen.

What's clear for now is that the Friars are a factor.

Honorable Mention: Miami Marlins Extend Giancarlo Stanton

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Giancarlo Stanton's 13-year, $325 million mega-contract with the Miami Marlins ranks as the biggest deal of the offseason in a literal sense.

And certainly it has the potential to be the most significant move as well. We're listing it here as an honorable mention, but really it deserves an "incomplete."

If Stanton stays in South Florida for a decade-plus and Miami manages to build a consistent winner around him, we'll look back on this as a watershed moment for the franchise.

Remember, though, the contract is structured with some significant caveats, as FoxSports.com's Dave Cameron explains:

"

The $325 million figure might end up being nothing more than a mirage. Because of the leverage he commanded, and potentially some lingering distrust of the franchise after its last spend-a-bunch-of-money-then-trade-everyone fake out, Stanton's representatives were able to negotiate an opt-out clause into the deal, meaning that he can choose to void the deal after the 2020 season.

"

So it's wait-and-see in Miami, as usual. Maybe Stanton, arguably the best power hitter in the game, will be the cornerstone of a perennial contender. Or maybe he'll see the writing on the wall and look for a payday elsewhere. 

That's a discussion for another offseason. 

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