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Top 15 Absolute Worst Contracts In Baseball Today

Wealthy, long-term contracts are initially marketed triumphantly by the franchise’s front office and eagerly celebrated by its fan base, each believing the newly-signed superstar will create a winning atmosphere for years … and years … and years …

However, those same rich deals usually become downplayed by the team’s PR staff and lamented by the fans when the one-time star inevitably displays diminished bat speed, defensive range, and arm strength.

Big contracts often are negotiated by players looking to be paid for past performances, aging All-Stars who are beyond their athletic peak, but still remain among the game’s most attractive attractions.

Mammoth deals prove to produce short honeymoons.

Eight of this season’s 17 richest MLB contracts can, at best, be considered financially irresponsible, at worse, a constant albatross to constructing a balanced roster.

The surprising aspect of the following listing is it does not include Alex Rodriguez or Prince Fielder, two top-five candidates, for sure. But they both retired the past few weeks so they had to be cut. Sure was difficult cutting A-Rod, though, considering he was paid $3 million for being a suspended player in 2014 and GM Brian Cashman once said: “Alex should just shut the f%#! up.”

Other honourable mentions include Seattle Mariners second baseman Robinson Canó (10 years, $240 million), Yankees outfielder Jacoby Ellsbury (seven years, $153 million), and Cardinals pitcher Mike Leake (five years, $80 million).

The dual $28 million deals to Detroit Tigers’ Miguel Cabrera and Justin Verlander get a pass because both are still producing star-like statistics. So, too, does Boston Rex Sox pitcher Rick Porcello. In the first season of a four-year, $82.5 million deal, Porcello has elevated his back-end rotation status to an AL Cy Young candidate.

The ultimate bad deal? How about the New York Mets being on the hook to pay Bobby Bonilla annual payments of $1.19 million until 2035.

Here are the Top 15 Worst Contracts in Baseball for 2016:

15 Melvin Upton Jr.

Adam Hunger-USA TODAY Sports

Leading off, the elder Upton.

It seems the more he changes his name, the fewer extra base hits he produces. Is B.J., oops, I mean Melvin Upton Jr., trying to hide from his lack of big-money production?

In 2012, Upton clubbed a career-high 28 home runs. And during the 3.66 seasons since? He entered the week with 45 homers with three teams. Covering his first 23 appearances since being acquired by the Toronto Blue Jays, Upton had yet to connect on a double or triple.

For that, Upton is owned approximately $15 million this season and $16 million for 2017.

After his big 2012 campaign, Upton darted Tampa Bay for the big-money (five years, $72.25 million) the Atlanta Braves offered. He hit .184 the first season under the deal; .208 the next.

He’s certainly not the first, but Upton is following a prominent pattern. Numerous players are failing to play up to their contacts. Eventually – inevitably - the players can’t hide from their unworthy paychecks.

No matter how many times the player changes his name.

14 Justin Upton

Rick Osentoski-USA TODAY Sports

Batting second, lil’ Upton.

Just like big brother, Justin Upton is struggling to live up to a big contract.

The younger Upton signed a six-year, $132.75 million deal with the Detroit Tigers last offseason to add power behind Miguel Cabrera and Victor Martinez.

From Opening Day, the timing of his swing and mental approach to batting were, to say the least, off. Six weeks into the season, pitchers didn’t need to “pitch” to Upton. The scouting report read: Throw a fastball down the middle for strike one. Then, throw a fastball at the outer half to induce a foul tip, strike two. Finally, put him away with a slider down and away, strike three. It sure looked easy.

The Tigers dished out the contract last winter to fill a void in left field its barren farm system could not produce. Last week, Upton was given a “mental health break” and did not start for three games. At the time he was suffering through a 0-for-12 slump and had struck out 139 times, fourth most in all of baseball.

Upton returned to the starting lineup last Sunday and slugged two three-run home runs. Could he play himself off this list by season’s end?

He will need to for the Tigers to crawl back into playoff contention.

13 Ryan Zimmerman

Steve Mitchell-USA TODAY Sports

Ryan Zimmerman was the franchise’s initial marketing chip following its move from Montreal. He has proven to be a solid player, if not an unproven cheater, but do you think the Nationals’ brass believes the six-year, $100 million extension he signed during February 2012 was a bit ambitious? Like two or three years ambitious?

Zimmerman will earn $14 million during 2016 and the next two seasons, before ballooning to $18 million for 2019. The club owns the 2020 option for $18 million.

Zimmerman has devolved the past three seasons from a power-hitting third baseman to rehabilitating first baseman following a series of throwing deficiencies and injuries.

After averaging 22 home runs his first eight full MLB seasons, Zimmerman has connected on just 34 the past three injury-plagued seasons combined.

The good news? At least Zimmerman last Friday was “cleared” by the commissioner’s office of the investigation surrounding a recent Al Jazeera report linking him to a PED ring.

12 CC Sabathia

Adam Hunger-USA TODAY Sports

Let’s see what $25 million gets the Yankees? An aging, undependable fifth starter, it appears. Just think, a few years ago, $25 million covered the top-three of a top-tier rotation. Now, its pays for one past-his-prime left-hander.

A millennial star, CC Sabathia signed an eight-year, $186 million deal with the Yankees, after acquiring the 2007 AL Cy Young Award winner from the Milwaukee Brewers.

Aided by Sabathia earning the ALCS MVP and posting a 19-8 regular-season record, the Yankees claimed the 2009 World Series. Sabathia remained an All-Star from 2010 through 2012, but since has struggled to remain healthy and in the rotation.

The past three seasons, Sabathia has gone 16-24. He carried a 6.94 August ERA into Tuesday’s start at the Seattle Mariners. That’s what the Yankees are getting for $25 million.

Look for the front office to execute the $5 million buyout this offseason.

11 Shin-Soo Choo

Jim Cowsert-USA TODAY Sports

The accounting for Shin-Soo Choo’s season can be summed up in the number of times he spent on the disabled list this season: four. In terms of his 2016 salary, that’s $5 million per DL trip.

The latest venture was initiated when Choo was hit by a pitch and was scheduled to undergo season-ending surgery. The other injuries included a strained right calf, a left hamstring strain, and a lower back inflammation.

Since joining the Rangers in 2014, Choo initially struggled with a career-low .242 batting average and now a season in which he produced seven home runs and 17 RBIs.

With $82 million owned to Choo over the next four seasons, this deal can be compared to a stereotypical Trump supporter, full of excuses and without substance.

10 Jason Heyward

Caylor Arnold-USA TODAY Sports

He was 26-years-old and on the free-agent market. Defensively, few are better. Offensively, his power numbers were down, but he still consistently got on base.

Jason Heyward was ready to take the world to the bank and was soon ushered by the Chicago Cubs agreeing to an eight-year, $184 million contract.

Now 27, the three-time Gold Glove outfielder is only two-thirds through the first season of the deal and already is losing playing time to youngsters like Jorge Soler and Matt Szczur.

Where will Heyward be when he’s 34 and nearing the end of the contract? In Kodak, Tenn., with the AA Tennessee Smokies?

Through 409 at-bats with the Cubs, Heyward had produced a .225 batting average, five home runs, and 32 RBIs.

Much like the Detroit Tigers did with Justin Upton, Chicago Cubs manager Joe Maddon gave the struggling Heyward the weekend off while in Colorado to “chill out a bit.”

Well, Denver certainly was a cool place to do that.

9 Matt Kemp

Jake Roth-USA TODAY Sports

Big-market franchises are just lining up to pay Matt Kemp’s baggage.

Where’s the line in front of me?

First came the Dodgers’ decision in 2012 to agree on an eight-year, $160 million contract. Then, two unfulfilling seasons later, the Dodgers agreed to unload Kemp during December 2014 and pay the Padres $32 million of the $107 million left on the deal.

The Padres took on the biggest contract in team history, believing they were receiving something similar to the 2011 version that slugged 39 home runs and placed second in NL MVP voting. But what did they receive? After undergoing shoulder and ankle surgeries, a post-trade physical revealed Kemp had arthritis in both hips.

For $21.5 million in 2016 and signed through 2019, Kemp was traded to the Atlanta Braves at the deadline. To finalize the deal, however, the Padres had to include financial considerations. The deal addendum was necessary for the Braves to add Kemp and his recent pedestrian production.

8 Carl Crawford

Jake Roth-USA TODAY Sports

As solid as Carl Crawford appeared at the start of his career, it’s not difficult to determine what happened the past several seasons, apart from signing for big bucks?

The hunger, the drive. Deposited.

When Crawford signed his seven-year, $142 million contract, Crawford was projected as a perennial All-Star who would continue to provide gap power and steal 50 bases per season.

He was young. He was talented. He just didn’t continue to develop.

Since he signed the deal, which pays him $20.75 million this season, Crawford emerged from spring training as a bench player. In his first 87 at-bats this season, Crawford is hitting .185 with no homers and six RBIs.

Since the start of 2011, Crawford had 32 total homers and this season was caught during his lone stolen base attempt.

Next season is the final year of Crawford’s contract, certainly one of the worst scouted in major league history.

7 Zack Greinke

Bill Streicher-USA TODAY Sports

Off the mound he walked, his head down. After recording just five outs, Greinke on August 14 yielded nine earned runs off 10 hits to the Boston Red Sox.

At $31.8 million, Greinke is scheduled to make the second-highest salary this season, the first of a six-year, $206.5 million deal.

Last season, Greinke registered a major leagues-best 1.66 ERA in 32 contract-year starts with the Los Angeles Dodgers.

But with ex-Dodgers teammate Clayton Kershaw drawling the game’s highest paycheck, Greinke found his green pasture in Arizona. But he left his recent success in Tinsel Town, where he combined to win 51 of 66 decisions from 2013-15. During his opening 18 starts with the Diamondbacks, Greinke allowed 56 earned runs, more than he surrendered in 2013 and 2015.

Greinke entered Thursday with a 4.30 ERA, nearly a full run greater than his career total (3.40).

Based on salary, here's your ace for five more years, Diamondbacks fans.

6 Joe Mauer

Brad Rempel-USA TODAY Sports

His gap power has gone AWOL. The power stroke Joe Mauer displayed at the start of his eight-year, 184 million deal, is now virtually nonexistent.

When he signed in 2011, Mauer was awarded the largest deal ever for a catcher. Essentially, he stopped catching in 2013.

At about the same time, Mauer’s power fell flat as injuries mounted. As a first baseman/DH, Mauer is coming up short. He slammed 28 home runs during 2009, setting up the big payday, but over the last seven seasons, his annual homer average is eight.

The first player selected in the 2001 draft, Mauer was named the 2009 AL MVP and captured the 2006 AL batting title. For that service, Mauer is scheduled to be paid a combined $46 million, on a team that this season will be challenged to win 60 games.

Cool ballpark, at least.

5 Ryan Howard

Bill Streicher-USA TODAY Sports

What was the worry? Why the rush? Sure, the Philadelphia Phillies wanted to secure a hard-hitting, fan-favourite for the long-term, but history says the team rushed to the bargaining table.

Then 30-year-old and delivering power to the historically exasperated Philly fans, Howard was under team control for two more seasons, but the Phillies wanted more.

The slugger swung from his heels at the opportunity to ink the five-year, $125 million extension.

Since 2012, Howard has averaged 18 homers per season. From 2005-11, he nearly averaged 41. Over the past five seasons, Howard entered Thursday with 610 strike outs and just 420 hits.

Needless to say, the Phillies will not be exercising its $23 million club option for 2017, instead initiating a $10 million buyout.

Like Zimmerman, at least he was cleared from the PED investigation surrounding the Al Jazeera report on his connections to a doping ring.

4 David Price

Tommy Gilligan-USA TODAY Sports

New Boston Red Sox President of Baseball Operations Dave Dombrowski last offseason peered into the vast payroll vault the Boston Red Sox offered and jumped at the new front-office opportunity.

“I can spend how much?”

It didn’t take Dombrowski long to seize on the opportunity, negotiating a seven-year, $217 million contract with pitcher David Price.

The left-hander jumped at signing the largest deal ever signed by a major leaguer.

And he only is expected to work every fifth day.

One wonders: How does this deal make sense long-term? How can Price live up to such a deal?

Just examine how Yankees pitcher CC Sabathia is being handled at the end of his mega-deal. Have you read the recent stories or listened to the “talking teeth” on cable’s sports shows?

To at least compare to Sabathia's first two seasons in New York, Price will have to win more than 40 games and deliver a World Series title. Good luck, David.

3 Pablo Sandoval

Bob DeChiara-USA TODAY Sports

Are we looking at the top free-agent bust of all-time?

For playing himself into a bench player, Pablo Sandoval will get paid $95 million over the life of his five-year deal with the Boston Red Sox.

After signing the deal, Sandoval’s World Series success evaporated, floated away in the outfield midst of a damp morning at Fenway.

He stopped hitting. He stopped fielding. Didn’t stop eating, though.

During an early season at-bat, Sandoval executed a big, looping swing, snapping his belt buckle. Sure would have cool to be a Boston columnist that day.

This is the October wonderkind who led the San Francisco Giants to three Series titles?

2 Josh Hamilton

Jim Cowsert-USA TODAY Sports

Here is a story of redemption. A story of betrayal.

A story not yet fully written. Or has it?

The Rangers on August 23, placed Josh Hamilton on unconditional release waivers and after three knee surgeries since last September, the door remains open for Hamilton to return and compete for a job next spring training.

The weaving journey the 1999 first overall pick has taken has been well documented. The promise. The drugs. The redemption. The five All-Star Game appearances. The 2010 AL MVP. The big deals. The deceptions. The knee.

Next year will be the final season of the five-year, $125 contract Hamilton signed with the Angels. It was not a good marriage. Hamilton admitted to drug relapses and was traded back to the Rangers. The Angels were so eager to rid themselves of Hamilton, they agreed to pay all but $2 million of the $48 million in salary obligations.

Hamilton last appeared in 2015, suiting up 50 games and clubbing eight home runs.

Is Hamilton’s baseball story ending? Stay tuned.

1 Albert Pujols

Kelvin Kuo-USA TODAY Sports

In 2012, Albert Pujols abandoned the St. Louis Cardinals for a 10-year, $240 million deal with the Los Angeles of Anaheim.

Instead of electing to become a Cardinal icon, the future Hall of Famer chose to play out his declining years with a deal that will cripple the franchise for a generation.

Until clubbing 40 home runs last season, Pujols had suffered subpar power seasons since leaving St. Louis prior to the 2012 campaign. During his 11-year stint with the Cardinals, Pujols annually averaged 40 homers. In Los Angeles, he is averaging 27.

The nine-time All-Star’s marketing value will increase over the next few seasons as he chases career marks and his presence in the locker room is immeasurable, yet the deal will not end until 2021, when Pujols will be 41.

The Angels have the best player in baseball, Mike Trout, and former best player in baseball, Pujols.

And not much else.

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Top 15 Absolute Worst Contracts In Baseball Today