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David Price was all smiles at his introductory press conference in Boston.
David Price was all smiles at his introductory press conference in Boston.Associated Press

Ranking the 2015-16 MLB Offseason's 15 Largest Contracts from Worst to Best

Karl BuscheckJan 8, 2016

It's good to be David Price and Jason Heyward.

During the 2015-2016 MLB offseason, the lefty ace and defensive whiz raked in contracts worth slightly more than $400 million combined.

The big question moving forward is just how well those megadeals will work out for their new employers, the Boston Red Sox (Price) and Chicago Cubs (Heyward).

In the process of ranking the 15 largest contracts (in terms of overall value) from worst to best, we considered two key factors.

The first factor was how well the specific move addressed both the short- and long-term needs of the given team. The second factor was how the individual contract compared to deals for similar players. Did Club X wildly overpay for a headliner, or does the price tag match up with other spending around the league?

Starting at No. 15—the worst deal of all—let's count down to No. 1—the best deal of the offseason. As it turns out, the same club bookends these rankings.

15. Jason Heyward, CF/RF, Chicago Cubs

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Jason Heyward certainly brings his glove to work.
Jason Heyward certainly brings his glove to work.

Contract Terms: Eight years, $184 million

2016 Opening Day Age: 26

There's no debating Jason Heyward's genius in the field. Per ESPN Stats & Info, he has saved more runs than any other outfielder since the start of 2011.

The debate here is whether the Chicago Cubs overpaid for the 26-year-old.

Right now, the answer to that question is a resounding "yes." Just look at the rest of the market. Alex Gordon, who is an older version of Heyward, signed for $72 million over four seasons. Meanwhile, guys like Yoenis Cespedes and Justin Upton still don't have any reported offers.

According to Bob Nightengale of USA Today, the Cubs weren't the only team that misread the market for big-name outfielders. As Nightengale reported, both the St. Louis Cardinals and the Washington Nationals were willing to give Heyward $200 over 10 years, which still works out to less than his annual average value with the Cubs.

But Heyward said no. And now the Cubs will be paying $23 million per year to a guy who profiles best as the No. 7 hitter at Wrigley Field.

14. Jeff Samardzija, SP, San Francisco Giants

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San Francisco doesn't seem to be overly concerned with Jeff Samardzija's dismal 2015.
San Francisco doesn't seem to be overly concerned with Jeff Samardzija's dismal 2015.

Contract Terms: Five years, $90 million

2016 Opening Day Age: 31

Pick any stat you want: Jeff Samardzija was brutal in 2015.

The Shark posted the third-worst ERA (4.96) among qualified starters and gave up more hits, runs and earned runs than any pitcher in the bigs.

Even after that dud of a contract season, the San Francisco Giants made a splash with a five-year, $90 million deal to bring Samardzija to the Bay Area.

Maybe Brian Sabean knows something the rest of the baseball word doesn't. After all, the executive vice president of baseball operations has one of the best eyes for talent in the game. Maybe Sabean and Co. think cavernous AT&T Park will be an ideal fit.

But giving $90 million to a guy who's posted a sub-4.00 ERA in only two of his seasons as a starter? Now that's a gamble.

13. Mike Leake, SP, St. Louis Cardinals

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In signing Mike Leake, St. Louis paid a premium price for a mid-rotation arm.
In signing Mike Leake, St. Louis paid a premium price for a mid-rotation arm.

Contract Terms: Five years, $80 million

2016 Opening Day Age: 28

It's not wise to question the decisions of John Mozeliak, the erudite general manager of the St. Louis Cardinals.

Still, his five-year, $80 million deal for Mike Leake is difficult to comprehend.

Simply put, Leake is just a guy. He's a durable guy—he's pitched at least 179 innings in each of the past four seasons—but just a guy nonetheless. As one scout put it to Jerry Crasnick of ESPN.com, he's a "No. 3½-type" starting pitcher.

Eighty million dollars for a No. 3½ type? That does not make sense.

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12. David Price, SP, Boston Red Sox

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According to one report, Boston was not David Price's top choice.
According to one report, Boston was not David Price's top choice.

Contract Terms: Seven years, $217 million

2016 Opening Day Age: 30

The Boston Red Sox finally reeled in that elusive ace by inking David Price to a seven-year, $217 million contract. As Bob Nightengale of USA Today reported, it took every last penny to convince Price to head to Fenway Park.

"Price, a native of Murfreesboro, Tennessee, was enamored with joining the [St. Louis] Cardinals, who have reached the postseason the last five seasons, with two pennants and a World Series title," Nightengale wrote. "Yet, the Red Sox's offer simply was too strong for him to refuse."

As Nightengale noted, Boston's offer included at least $30 million more than what the Redbirds were willing to pay. That's one serious overreach.

11. Zack Greinke, SP, Arizona Diamondbacks

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Zack Greinke is the star of Arizona's wild winter.
Zack Greinke is the star of Arizona's wild winter.

Contract Terms: Six years, $206.5 million

2016 Opening Day Age: 32

Yes, $206.5 million.

That's a ton of loot to give to anyone—especially a 32-year-old starting pitcher. To be fair, there aren't many 32-year-old starters like Zack Greinke, who posted a shiny 1.66 ERA in 2015.

Rick Honeycutt, his former pitching coach with the Los Angeles Dodgers, believes there's still plenty more to come for the righty ace. Here's Honeycutt's take from an interview on SportsNet L.A., via FoxSports.com:

"

You've seen him each year we've had him, and each year he gets better as the season goes on. He's in great shape, he adds and subtracts to his pitches when he wants to. He can continue to pitch just like [Greg] Maddux into his 40s. He has that ability, because he has the pitches already and makes the adjustments with the pitches he has.

"

That comparison is lofty praise. And it's worth noting that the Arizona Diamondbacks won't be worried about Greinke's 40s, but rather his age-32 to age-37 seasons. If the club's new pitching star ages like the Mad Dog, this deal will be a shrewd one for Arizona.

10. J.A. Happ, SP, Toronto Blue Jays

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J.A. Happ will be looking for better results in his second go-around with Toronto.
J.A. Happ will be looking for better results in his second go-around with Toronto.

Contract Terms: Three years, $36 million

2016 Opening Day Age: 33

The question here is simple: Just which J.A. Happ will show up for the Toronto Blue Jays in 2016?

Last year, he had one strange season.

In 21 outings with the Seattle Mariners, the left-hander posted a 4.64 ERA and allowed the opposition to tee off to the tune of a .279 average. But following a summer swap to the Pittsburgh Pirates, Happ was a totally different pitcher. In 11 starts, he compiled a 1.85 ERA and a .221 opponents' average.

Now, the starter is headed back to the American League with the Blue Jays, for whom he was less than stellar in his previous stint. Over parts of three seasons from 2012 to 2014, Happ tallied a 19-20 record and a 4.39 ERA for Toronto.

At a price tag of $36 million over three seasons, this deal isn't a major liability for the Jays. Then again, it doesn't look nearly as team-friendly as the two-year, $26 million deal the club gave Marco Estrada.

9. Denard Span, CF, San Francisco Giants

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Denard Span is looking for a big bounce-back after an injury-riddled campaign.
Denard Span is looking for a big bounce-back after an injury-riddled campaign.

Contract Terms: Three years, $31 million

2016 Opening Day Age: 32

After injuries wrecked his 2015, Denard Span had the look of an intriguing buy-low candidate.

But handing a three-year deal to a guy who had hip surgery at the end of last season isn't exactly buying low. Per Jon Heyman of MLB Network and WFAN, Span's new deal is worth $31 million with $5 million in incentives.

There's no question about it—Span provides the San Francisco Giants with some much-needed cover in left and center field, where Gregor Blanco and Angel Pagan were the top in-house options.

But a one-year deal with an option would have been a far safer play. What makes the move even more puzzling is that the Giants could have had a comparable player in Nori Aoki for $5.5 million in 2016, but they declined his option at the beginning of the offseason.

8. Daniel Murphy, 2B, Washington Nationals

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Daniel Murphy provides Washington with a much-needed lefty bat.
Daniel Murphy provides Washington with a much-needed lefty bat.

Contract Terms: Three years, $37.5 million

2016 Opening Day Age: 31

It's not easy to find quality second basemen.

Mike Rizzo, the general manager of the Washington Nationals, knows that firsthand. As James Wagner of the Washington Post wrote, the Nats turned to Daniel Murphy after whiffing on Ben Zobrist and Brandon Phillips.

The owner of a .288 average across seven seasons, the left-handed hitter can definitely swing it. But his seven-home run outburst in October was a mirage, not a sign of what is to come. In 903 regular-season contests, Murphy has gone yard 62 times.

His glove also looms as a serious concern. Last season, Murphy cost the New York Mets six runs at second base in just 69 games. From 2012 to 2014, he never cost the team fewer than 10 runs.

7. Ben Zobrist, UTL, Chicago Cubs

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Ben Zobrist is once again playing for his old boss, Joe Maddon.
Ben Zobrist is once again playing for his old boss, Joe Maddon.

Contract Terms: Four years, $56 million

2016 Opening Day Age: 34

Joe Maddon, the skipper of the Chicago Cubs, loves versatility. That's why a reunion with the switch-hitting Ben Zobrist makes so much sense for Maddon and the Cubs.

Zobrist will spend most of his time at second base, but his true position will be super-utility man.

"It's a position, it's an absolute position, just like second base or left field is," Maddon explained to Joe Lemire for USA Today. "A real legitimate SU guy is a position, and it permits you to do so many different things with your lineup daily and so many different things to get progress daily."

With Zobrist in the mix, Maddon will have the flexibility to start the veteran at second and then shift him to one of the outfield corners in the late innings to cover for a guy like Kyle Schwarber.

Really, the only downside—and it's not an insubstantial one—is Zobrist's age, as he'll be 38 when this four-year agreement ends.

6. Johnny Cueto, SP, San Francisco Giants

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Johnny Cueto brings one heck of a track record to AT&T Park.
Johnny Cueto brings one heck of a track record to AT&T Park.

Contract Terms: Six years, $130 million

2016 Opening Day Age: 30

The major concern here relates to Johnny Cueto's ugly second half in 2015.

Following his trade to the Kansas City Royals in July, the right-hander posted a 4.76 ERA and .307 opponents' average in 13 starts. Those numbers are bad—really bad.

But even with that bummer of a second half, Cueto has still been impressive over the past five campaigns.

As Aaron Gleeman of NBCSports.com noted, the Dominican's 2.71 ERA since the start of 2011 is second only to that of Clayton Kershaw (2.11). By that measure, the San Francisco Giants just acquired the best pitcher not named Kershaw.

And the brass in San Francisco also deserves some credit for how it structured Cueto's deal. He has the ability to opt out after the 2017 season, when he'll still be just 31 years old. As a result, Cueto has extra incentive to pitch well for the Giants over the next two seasons.

5. Scott Kazmir, SP, Los Angeles Dodgers

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Scott Kazmir will make his National League debut in 2016.
Scott Kazmir will make his National League debut in 2016.

Contract Terms: Three years, $48 million (Kazmir can opt out after the first year)

2016 Opening Day Age: 32

For the big-money Los Angeles Dodgers, this is a low-risk, high-reward move.

Sure, Scott Kazmir isn't going to do a Zack Greinke impression as the Dodgers' No. 2 starter, but he's far from a slouch. In 2015, the lefty sported a 3.10 ERA, which was the fourth-best mark in the American League. Now, he gets to pitch in the Senior Circuit, where he won't have to worry about designated hitters.

Los Angeles also structured the deal in a way that gives Kazmir extra incentive to shine in 2016. Per the terms of his contract, he can opt out after the 2016 season.

"From a business perspective, I think it's always good to have options," Kazmir told Steve Dilbeck of the Los Angeles Times.

But the Dodgers have options, too. As Bill Shaikin of the Times reported, if Kazmir does leave, L.A. could end up snagging a draft pick via the qualifying-offer process.

4. Darren O'Day, RP, Baltimore Orioles

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Darren O'Day has been lights out since arriving at Camden Yards in 2012.
Darren O'Day has been lights out since arriving at Camden Yards in 2012.

Contract Terms: Four years, $31 million

2016 Opening Day Age: 33

As the Kansas City Royals have demonstrated, electric relievers are valuable.

While the New York Yankees have received the most attention for trying to copy that formula, the Baltimore Orioles are quietly assembling another nasty late-innings punch.

Closer Zach Britton is under team control for the next three seasons, and setup man Darren O'Day will be around for the next four campaigns.

Last summer, O'Day earned his first All-Star nod, but the 33-year-old has been one of the filthiest relievers in the game since joining the O's back in 2012. Over the stretch, the sidearmer has posted a 1.92 ERA and racked up 283 punchouts in 263 frames.

If he keeps delivering those kinds of numbers, O'Day will be a great buy for the Orioles on an average annual salary of $7.75 million over the next four seasons.

3. Alex Gordon, LF, Kansas City Royals

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Alex Gordon isn't leaving Kansas City after all.
Alex Gordon isn't leaving Kansas City after all.

Contract Terms: Four years, $72 million

2016 Opening Day Age: 32

As recent history has made clear, Kansas City Royals general manager Dayton Moore is one savvy team builder.

The exec's latest stroke of brilliance was taking a deliberate approach to negotiations with Alex Gordon before keeping the veteran anchored in left field at Kauffman Stadium with a four-year, $72 million pact.

The reigning World Series winners stand to get a healthy return on that investment. Per ESPN Stats & Info, Gordon ranks third among all outfielders in WAR over the past five seasons. The two guys ahead of him? Mike Trout and Andrew McCutchen. That's some pretty good company.

2. Jordan Zimmermann, SP, Detroit Tigers

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Jordan Zimmermann will fit like a glove in Motown.
Jordan Zimmermann will fit like a glove in Motown.

Contract Terms: Five years, $110 million

2016 Opening Day Age: 29

Importing a big-time starting pitcher made all sorts of sense for the Detroit Tigers after their rotation ran up the fourth-worst ERA in the bigs in 2015.

Knowing that stat all too well, general manager Al Avila didn't waste any time diving into the pitching market, and he scooped up Jordan Zimmermann on Dec. 1.

"The Tigers' quick-strike signing of ... Zimmermann—for the vast but strangely economical sum of five years and $110 million—was very much an indication that the Tigers remain in it to win it," Gabe Lacques of USA Today wrote.

Vast but strangely economical sum, indeed.

While $110 million is a ton of money, it's actually not that much when considering the free-agent market for high-end starters. Zack Greinke and David Price, who are admittedly a tier above Zimmermann, each easily eclipsed the $200 million plateau. Johnny Cueto, who is Zimmermann's closest comp this winter, ended up reeling in six years and $130 million.

In this case, the swift action of Avila should end up paying major dividends for Detroit.

1. John Lackey, SP, Chicago Cubs

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John Lackey will remain in the NL Central in 2016.
John Lackey will remain in the NL Central in 2016.

Contract Terms: Two years, $32 million

2016 Opening Day Age: 37

There's so much to like about this deal.

Let's begin by pointing out that front-line free-agent starters aren't supposed to be available on two-year deals. And that's exactly who the Chicago Cubs are getting in John Lackey. Last season, he worked 218 innings and spun a 2.77 ERA, which ranked seventh in the National League—ahead of Max Scherzer and Madison Bumgarner.

The kicker is that as a result of Lackey swapping Busch Stadium for Wrigley Field, the St. Louis Cardinals ended up having to spring for another right-hander (Mike Leake) who can't touch the wily vet.

Note: All stats courtesy of Baseball-Reference.com and MLB.com. All salary information courtesy of Cot's Baseball Contracts on BaseballProspectus.com.

If you want to talk baseball, find me on Twitter @KarlBuscheck.

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