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Top 15 Worst MLB Free Agent Signings Since 2000

Let’s face it…while free agency is exciting and much fairer for the players, it comes with multiple faux pas. Most times a ball player isn’t worth the money he’s given. It feels like a rare occurrence, when a free agent contract works out. Because of this, most teams in baseball stay out of bidding wars.

By this list, you’ll notice, it’s only four or five teams who engage said bidding wars. Why? Because they have the money. If a contract with a new player falls flat, the impact on their team is felt far less.

The best of these big bidders, mix timely signings with a strong farm system. This creates and fosters a healthy environment between owner and organization. The team gets to “bring up” young stars, while solidified stars, act as the mentors to these players.

But again…often, a deal with one of those more “solidified” stars, goes real sour. Judging by this list of the fifteen worst signings since 2000, you’ll soon agree.

*Other cruddy, but not listed signings: Barry Zito, Oliver Perez, Carl Crawford, B.J Upton, Jason Schmidt, Pablo Sandoval, Hanley Ramirez, Jayson Werth.

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15 C.J. Wilson: 5 years, $77.5 million (Angels)

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The Winter of 2011, was a big one for the Angels. They’d wrapped up a contract for Albert Pujols, but weren’t finished. That same day, they locked up Rangers ace, C.J. Wilson, to a 5-year, $77.5 million deal. Wilson, by all measurements, was not going to wow you, but he was a rare lefty, eating up innings and accruing quite a bit of strike outs.

The two years prior, Wilson posted a 31-15 record with a 3.18 earned run average. He finished top five in strike outs, and twice voted top six in Cy Young voting. But I remember, clearly, how little the Rangers tried to keep him. It was as if they knew, something was soon going to go wrong; like Wilson was overrated, overhyped, cashing in at a time post-prime.

And boy were they right! Wilson was nowhere near the player he’d been in Texas. His command fell apart, injuries riddled him; he looked shaky and insecure. With the Angels, Wilson led the league in walks, once. The other four years, finished top three, twice. The lone blight coming in 2013, when Wilson finished 17-7, and top five in strike outs. He didn’t play the final year and a half of his contract because of a foot injury, an injury chronically in question, by teammates and ownership.

14 Albert Pujols: 10 years, $240 million (Angels)

Rick Scuteri-USA TODAY Sports
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I’m being kind, ranking Pujols so low on this list. One could argue his contract is the worst in baseball history.

The Pujols contract is interesting. It proves, arguably the greatest player of his generation, can be a bad pick up. I mean, think about it this way: Before Pujols joined the Angels, he was already a Hall of Famer. Over eleven years with the Cardinals, Pujols went to nine All-Star games, won three MVPs, two World Series, five Silver Sluggers, two Gold Gloves, mashed 445 home runs and hit .328. He was, by all standards, the greatest player in Cardinals history, the reason “the shift” was created, to take away line drives to left.

The fall off, has been painful. Fans have watched a legend deteriorate quickly, becoming a limited DH, with dwindling power. But, even then, Pujols hasn’t been horrible. Over five years with the Angels, he’s averaged 30 home runs and nearly 100 runs batted in. He’s made one All-Star team. He's also been crucial in the mentorship and development of Mike Trout.

12-million a year, sure. But that fat 24, is a hard number to swallow.

13 Manny Ramirez: 2 years, $45 million (Dodgers)

Jayne Kamin-Oncea-USA TODAY Sports

Traded the Summer of 2008, from the Red Sox to the Dodgers, Manny went bananas. In 53 games, he hit .396, with 17 home runs, 53 runs batted in and a .489 OBP. Dodger fans were chanting his name. He was adored. It made total sense to re-sign him that Winter to a short-term deal.

When the Dodgers inked Ramirez to $45-million over two years, they thought they’d be getting that superstar middle of the order bat, driving runs in and adding flare. But that’s when things went real south. Ramirez was slapped with a 50-game suspension for taking an illegal enhancement, and he never recovered. After the suspension, he struggled with injuries, chronic complaints, became more of a locker room cancer than a fun, loving humorist. His number weren’t horrible, but he wasn’t on the field enough to warrant his 22.5 million a year. Traded in 2010 to the White Sox, Ramirez career officially flat lined. No more Man Ram. Just an average overpaid DH, with a bad attitude.

12 Jason Bay: 4 years, $66 million (Mets)

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I never got the whole craze over Jason Bay. Sure, he was serviceable. He had power if in the right kind of lineup, hit a steady average. But he never wowed me like he did for others.

Bay is known as the greatest baseball player in Canadian history. For the first nine years of his career, he was good. Made three All-Star teams, won Rookie of the Year, hit over 30 home runs on four occasions. His best year coming in 2009 with the Red Sox, when he hit a career best 36 home runs, drove in 119 runs; earning a Silver Slugger award, and top ten in MVP voting. Like any smart business man, he cashed in.

That Winter, he signed with the New York Mets, to the tune of 16.5 million a year for four years. The Mets expected the Bay with the tremendous power and high OBP, but got, as I expected, a player with many vulnerabilities at the plate. Without the protection, he had in Boston, Bay struggled. In three years with the club, he missed 202 games. When at the plate, he looked lost. Over three years, he hit .234 with a combined 26 home runs. Not kidding.

11 Milton Bradley: 3 years, $30 million (Cubs)

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If you remember clearly, Bradley was one hell of a ball player. The guy was a tremendous glove, could pressure the defense and get on base. He was also known for a charismatic, outlandish attitude, one that saw him spend much time, lambasted by media, fans, teammates, and several ownerships.

When Bradley signed with the Cubs, he’d been exiled by the Texas Rangers. Not only could the dude not stay healthy, he couldn’t keep his mouth closed. Because of this, he wasn’t the hottest free agent commodity. But he had shown flashes of star potential. 2008, Bradley hit .321 with 22 home runs and a .436 OBP. Because of this, the Cubs took a risk.

That risk didn’t pan out too well. In one year with the team, he was mired in controversy. His character and drive in question, he hit .257 with 12 home runs. The Cubs gladly shipped him to Seattle, where he finished out the last two years of his career.

10 Matt Kemp: 8 years, $160 million (Dodgers)

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Matt Kemp’s ceiling was short lived. It only lasted one year, a year that saw Kemp put up outrageous numbers: .324 batting average, 39 home runs, 126 runs batted in and 40 stolen bases. The Dodgers inked Kemp to a contract extension worth $160 million that Winter, making him one of the richest men in baseball. Not technically a free agent, Kemp’s contract is still worth mentioning on this list.

He never lived up to the expectations, nor the contract. A year into the deal, Kemp’s numbers plummeted. His average fell to .270. Power numbers to six home runs and 33 runs batted in. He couldn’t stay healthy. He looked out of shape, lazy. Lost among that flurry of wealth. Never gaining his old form, the Dodgers had enough, dealing Kemp to the Padres in 2015. He now plays for the Braves. His numbers are serviceable, but the man’s grossly overpaid.

9 Daisuke Matsuzaka: 6 years, $52 million (Red Sox)

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Dice-K, remember him? The major Japanese hurler with a five-pitch arsenal? Time flies so quickly, we forget these big-name guys who splashed for a short span then faded into obscurity.

Matsuzaka’s first year in the league, was a wonder. It looked like the Red Sox inked a steal. At times, he felt unhittable. His first year in the league, he won 15 games, finished fourth in Rookie of the Year voting, and was integral in leading the Red Sox to the 2007 World Series. He followed that campaign, with 18 wins in 2008. That year, he finished fifth in Cy Young voting. He looked poised for a long career of dominant top tier pitching.

And then, what happened? Injuries happened. Dice-K spent more time starring on the DL than whiffing opposing teams' studs. Over the last four years of his deal, Dice-K won a combined 17 games, with a 5.52 ERA.

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8 Kei Igawa: 5 years, $20 million (Yankees)

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Igawa was the lesser known Japanese prospect, but was hotly pursued by multiple teams the same Winter of 2006. Unlike Dice-K though, Igawa never had any success. From day one, he languished with the Yankees, getting knocked around by opposing teams. His rookie year, he posted a stat line of 2-3 with a 6.25 earned run average. Because of his abysmal performance, the Yankees demoted him to their minor leagues, where he played out the rest of his lucrative deal.

While four million a year doesn’t sound like a horrendous loss to a mega organization, like the Yankees, consider this: Not only did they pay the full $20 million to Igawa, but an additional $26 million for just his bidding rights. Make that $46 million over four years, for a man who won them two games. Now you get my point.

7 Chan Ho Park: 5 year, $65 million (Rangers)

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The Korean right hander, had a solid first half of his career. From 1997 to 2001, Park won 75 games for the Dodgers. He finished top five in strike outs four times, and posted a manageable earned run average of 3.71. He went to one All-Star game, and held his role as a reliable middle rotation guy.

The winter of 2001, Park became a free agent. The Dodgers weren’t interested in his asking price, so they let him walk, and the Rangers gladly swooped him to the tune of $13-million a year over five years.

The results were hard to swallow. Over three and a half years with the club, Park battled innumerable injuries. His stats followed as suit, winning a total of 22 games. He posted an earned run average of well over six, leading the league in hit batters, in 2002.

6 Nick Swisher: 4 years, $56 million (Indians)

Jerome Miron-USA TODAY Sports
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Remember when Nick Swisher was relevant? You don’t? Me, neither. The man with that gimmicky look to his smile and game, clowned the Indians into giving him a contract nowhere near his worth.

Who knows what the Indians were thinking that winter. Swisher, up to that point, had played eight years in the league. Over those eight years, hit .260 with an average of 24 home runs per year. Not bad, by any means. But not 14-million a year worthy, when you consider the guy was an average defensive Right Fielder.

What happened after the signing, is to be expected. Swisher his 32 home runs over two and a half years, with a .228 average.

5 Carl Pavano: 4 years, $39 million (Yankees)

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Over nine years, Pavano did absolutely nothing with the Montreal Expos and Florida Marlins. The Winter the Yankees signed him, he’d put up a fluke season with Florida, winning 18 games and posting a 3.00 earned run average. That season, the fluke year, he went to an All-Star game and finished sixth in Cy Young voting.

But why all the money to a guy who did nothing the eight years prior? I’ll never get it. The Yankees at the time were into outlandish spending, so they threw money at him and told him to win them some games. That…he never did.

Over three years with the Yankees, he won nine games and posted a borderline six earned run average. The Yankees dealt him to Cleveland the last year of his contract, but even then, opted to pay most his remaining salary. That’s a price tag of over four million, per win. Ouch.

4 Gary Matthews Jr.: 5 years, $50 million (Angels)

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Matthews Jr. is the outfield version of Pavano. For ten years, he played for five teams (some twice!), floundering in obscurity. When he finally found some traction with the Rangers, he was nearing 30 years of age, past his prime, and still, at that point, just average. The fluke year happened in 2006, when Matthews Jr. went to an All-Star game, posting a batting average of .313 with 18 home runs and 18 stolen bases.

The Angels, as you’ve seen by this list, banked way too much money on a Texas Ranger. Matthews Jr. did what he’d done his whole career prior, playing an average outfield, and hitting like a lower of the order hitter. Not the big bat the Halos were expecting. Over three years, Matthews hit .248 with 30 home runs. The Angels shipped him to the Mets, but still forked over part of his remaining two years.

3 Alex Rodriguez: 10 years, $275 million (Yankees)

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Like Pujols, it’s weird putting a legendary, all-time hitter on this list. Rodriguez – personality, scandal and all –is bar none, a top ten talent in league history, someone critics and pundits will long admire for both his defensive and offensive attributes.

In 2008, the Yankees re-signed A-Rod to a deal that was the largest in sports history. A deal that would pay him into his early 40s. Like A-Rod had done the previous 14 years, he played like the superstar he was, the first year of the deal. He hit 30 home runs with a .286 batting average. His .402 OBP the best he’d posted in three years. That Winter, alongside Derek Jeter, Rodriguez led the Yankees to the World Series. Everything seemed and felt okay.

But after 2009, Rodriguez began to fall apart physically. From 2010-2016, A-Rod hit .258 with a combined 113 home runs. He missed all of 2014 with an infamous scandal, that defamed the Yankees organization and tainted his legacy.

The deal feels like the bad omen that caused it all.

2 Mike Hampton: 8 years, $121 million (Rockies)

: Rick Scuteri-USA TODAY Sports
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Who, in their right mind, signs a pitcher to an eight-year deal? Let alone, a deal this big? General rule of thumb with pitchers: four years, with options for a fifth and sixth.

When the Rockies signed Mike Hampton to his outrageous contract, they thought they were shoring a solid rotation, beginning with Hampton and continuing with notable bust, Denny Neagle.

Not so. The lights-out-lefty with the strike out pitch, looked shell shocked…like he better belonged in a Softball league, posting a 21-28 record with a 5.91 earned run average in his two years with the team.

Somehow the Rockies got rid of him. Traded him to the Braves, taking a portion of his remaining deal. Hampton spent the remainder of his contract injury riddled and obscure.

1 Josh Hamilton: 5 years, $125 million (Angels)

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Josh Hamilton is the saddest story. The man could have had everything. Players admired him. Saw him as one of the league’s future legends. Every owner wanted him. He was handsome. He had that gorgeous upturned left-handed swing, intangible power, an unrivaled glove in the outfield.

The demons were just too big. Drug problems, character issues, a lack of drive. A cocktail, no hero can overcome in sports. It’s hard to believe Hamilton put up some of the years he did between all the struggles. In 2008, he hit .302 with 32 home runs and 130 runs batted in. In 2010, he hit .359 with 32 home runs and an OPS of 1.044. That year he won an MVP. In 2012, he went bonkers again, slashing .285 with 43 home runs and 128 runs batted in. Get my point?

It makes sense why the Angels took a risk on him the winter of 2012. They imagined a middle order with Trout, Pujols and Hamilton. You really can’t blame them. But, like most big deal, especially deals with guys who have a history of ongoing issues, the deal became one of the worst ever. I think the worst since 2000.

In two years with the Angels, Hamilton missed 84 games. Drug issues resurfaced. His family fell apart. Thus, his abilities on the field, scattered and mediocre. During that span, he hit .266 with 32 combined home runs. He possessed the highest strike out rate in the league. The Angels had enough and they dealt him.

Since, he’s done nothing, but not play while collecting his herculean pay.

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