MLB Power Rankings: The 10 Most Regrettable Signings of the Offseason

Not every offseason signing is going to be perfect. Even with all the scouting tools out there, it's still difficult to properly evaluate a player and predict his performance going forward. Sabermetricians like Bill James get paid good money to predict what the players are going to accomplish, but the reality is that it's pretty much a crapshoot.

Most of the major free agents have signed on with new teams already and that means this is a good opportunity to evaluate those moves. We can't predict exactly what these 10 players will do, but we can say with somewhat more certainty that their new teams will regret signing them.

Here's a look at those 10 players, and remember: general managers are human beings too.

10. Jayson Werth (7 Years, $126 Million)

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WASHINGTON, DC - DECEMBER 15: Jayson Werth #28 of the Washington Nationals poses before being introduced to the media on December 15, 2010 at Nationals Park in Washington, DC. (Photo by Mitchell Layton/Getty Images)

This is without a doubt the most ridiculous contract handed out to a free agent this offseason. But the Washington Nationals knew they had to overpay to get Werth, and they did exactly that.

Werth is an outstanding baseball player who had a .921 OPS last season after smashing 46 doubles and 27 home runs. He can hit for power, hit for average, play the outfield, and even steal a few bases. He's a little old (31) to be the kind of player a franchise builds around, but that's not why the Nationals signed him.

Washington overpaid Werth so he could make the Nationals into a legitimate baseball team—one that is actually capable of competing for a playoff spot. You can't put a price tag on success.

9. Joaquin Benoit (3 Years, $16.5 Million)

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ARLINGTON, TX - OCTOBER 09: Joaquin Benoit #53 of the Tampa Bay Rays throws a pitch against the Texas Rangers during game three of the ALDS at Rangers Ballpark in Arlington on October 9, 2010 in Arlington, Texas. The Rays won 6-3. (Photo by Stephen Dun

It's pretty much never a good idea to give a reliever a long-term deal, but at least the Detroit Tigers didn't have to surrender a draft pick to get Benoit.

Benoit's career has taken an interesting path. He was originally brought up as a starter for the Texas Rangers and then transitioned into a reliever full-time in 2006. He always threw hard but struggled with his control and as a result had a 4.79 career ERA in his eight years in Texas.

But then he went to Tampa Bay and everything seemed to click. He made 63 appearances and emerged as one of the best set-up men in the game, earning a 1.34 ERA, an 11.2 SO/9 rate and a 1.6 BB/9 rate. If he can maintain that kind of performance for the Tigers then he may actually be worth the $16.5 million. It's definitely a risk, though.

8. Scott Downs (3 Years, $15 Million)

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TORONTO - SEPTEMBER 23: Scott Downs #37 of the Toronto Blue Jays pitches against the Seattle Mariners during the game on September 23, 2010 at Rogers Centre in Toronto, Ontario, Canada. The Blue Jays defeated the Mariners 1-0. (Photo by Brad White/Getty

Downs was one of the top relievers on the market before agreeing to a deal with the Los Angeles Angels of Anaheim. 

The 34-year-old has been fantastic in his six seasons in the AL East, sporting a 3.13 ERA in over 400 innings. He's not an overpowering pitcher, but he limits his mistakes and is fantastic against left-handed hitters.

He'll get to pitch against easier lineups in the AL West, but the chances of him keeping this up into his late 30's are slim to none. The Angels had to throw some money around this offseason, but Downs isn't the right guy to be throwing it at.

7. Matt Guerrier (3 Years, $12 Million)

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NEW YORK - OCTOBER 09: Matt Guerrier #54 of the Minnesota Twins throws a pitch against the New York Yankees during Game Three of the ALDS part of the 2010 MLB Playoffs at Yankee Stadium on October 9, 2010 in the Bronx borough of New York City. (Photo by

Guerrier has made at least 73 appearances in each of the last four seasons for the Minnesota Twins and owns a career 3.38 ERA. The 32-year-old righty has always been a great contributor and should be solid pitching in the National League.

But it's impossible for Dodger's GM Ned Colletti to justify signing a Type A free agent who is a reliever with no chance of ever becoming a closer. There are much better ways to spend $12 million.

6. Russell Martin (1 Year, $4 Million)

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LOS ANGELES, CA - JULY 25: Catcher Russell Martin #55 of the Los Angeles Dodgers jumps onto a rail beside the New York Mets dugouts as he pursues a pop foul ball that fell into the stands on July 25, 2010 at Dodger Stadium in Los Angeles, California. T

Yes, $4 million is like pocket change for the New York Yankees. But they would have been better off throwing it at a relief pitcher than at this 27-year-old catcher.

Martin was once one of the best players at his position. He made consecutive All-Star appearances in 2007 and 2008, and was great defensively. But all of his numbers have gone down each of the last four seasons and now he's a borderline starter.

Martin missed a third of the 2010 with a hairline fracture in his right hip. He had surgery to repair the fracture in his hip, but this is clearly not the same player anymore. 

He'll be the Yankee's starting catcher to open the season and it would be a major accomplishment for him to stay healthy, and on the roster, for all of 2011.

5. Adrian Beltre (6 Years, $96 Million)

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SEATTLE - SEPTEMBER 15: Adrian Beltre #29 of the Boston Red Sox bats against the Seattle Mariners at Safeco Field on September 15, 2010 in Seattle, Washington. (Photo by Otto Greule Jr/Getty Images)

Not sure how Scott Boras got Beltre $96 million when there were only two teams half-heartedly bidding for the third basemen. But I guess there's a reason that he's the best agent in the game.

Still, $96 million is a hefty price tag for the 31-year-old. He's a terrific player and one of the best defensive third basemen in the game, coming off a season in which he hit a career-high 49 doubles and 28 home runs while batting .321 with a .553 slugging percentage.

However, this is a guy who in his career only has two seasons in which he's driven over 100 runs, or earned an OPS over .900. If he can repeat what he did in 2010 for the Boston Red Sox over the next six seasons, then sure, $16 million/year is a pretty fair salary. But there is nothing to suggest that he is capable of repeating that performance. 

4. Paul Konerko (3 Years, $37.5 Million)

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CHICAGO - AUGUST 10: Paul Konerko #14 of the Chicago White Sox hits a double against the Minnesota Twins at U.S. Cellular Field on August 10, 2010 in Chicago, Illinois. The Twins defeated the White Sox 12-6. (Photo by Jonathan Daniel/Getty Images)

Everyone thought the 34-year-old slugger was done in 2008 when he finished the season batting just .240 and hitting only 22 home runs. Then he came back in 2009 and improved to .277 with 28 home runs, still well below his career average. Then in 2010 he was one of the best hitters in baseball, batting .312 with a career-high .977 OPS and 39 home runs.

Huh?

Konerko somehow managed to have the best season of his career at the age of 34, and was handsomely rewarded with a three-year contract. He's a very good hitter, but his 2010 campaign is either a serious aberration or evidence that Konerko found a very effective performance-enhancing drug.

I'm going to go with the former and say that there's no way Konerko is able to repeat what he did in 2010, meaning that the White Sox made a big mistake handing him almost $40 million to finish his career in Chicago.

3. Carlos Pena (1 Year, $10 Million)

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ARLINGTON, TX - OCTOBER 9: Carlos Pena #23 of the Tampa Bay Rays hits a two run home run in the ninth inning against the Texas Rangers during game three of the ALDS at Rangers Ballpark in Arlington on October 9, 2010 in Arlington, Texas. The Rays won 6-

How Pena got $10 million, while Derrek Lee got just $7.5 million, to be the Cubs first baseman is one of the great unanswered questions of the offseason.

This is the same player who batted .196 last season while striking out 158 times. His OPS dropped to .732 (career .841) and he only recorded 95 hits all season. The power is still there (144 home runs in the last four seasons), but Pena doesn't make enough contact to be earning an eight-figure salary.

Pena is 32 and left-handed, which gives him a bit of an advantage over other players on the market. But the Cubs could've saved themselves a whole lot of money by going after someone like Lyle Overbay or Edwin Encarnacion instead. 

In case you're wondering, here are the wins above replacement player (WAR) from last season for some of the free agent first baseman Chicago could've landed, and what they'll be making next season.

Carlos Pena: 1.1 WAR ($10 million)

Lyle Overbay: 2.4 WAR ($5 million)

Edwin Encarnacion: 1.6 WAR ($2.5 million)

Derrek Lee: 1.5 WAR ($7.5 million)

Adam LaRoche: 1.2 WAR ($7 million)

Aubrey Huff: 5.9 WAR ($10 million)

2. John Buck (3 Years, $18 Million)

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NEW YORK - AUGUST 03: John Buck #14 of the Toronto Blue Jays bats against of the New York Yankees on August 3, 2010 at Yankee Stadium in the Bronx borough of New York City. The Jays defeated the Yankees 8-2. (Photo by Jim McIsaac/Getty Images)

The 30-year-old catcher had the best season of his career in 2010, hitting .281 and slugging .489 while launching a career-high 20 home runs and making his first All-Star team. He's one of the better backstops in baseball and has a good amount of pop.

But how he got the Marlins to give him $18 million is anyone's guess. Buck's a career .243 hitter with a .722 OPS. He strikes out a lot and he has no speed. Yet, Florida somehow felt that it was a good idea to triple his annual salary instead of giving that cash to someone who deserved it (like Dan Uggla).

Go figure.

1. Derek Jeter (3 Years, $51 Million)

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TAMPA, FL - DECEMBER 07: Shortstop Derek Jeter of the New York Yankees talks to the media during a press conference to announce his new contract with the club on December 7, 2010 in Tampa, Florida. (Photo by Tim Boyles/Getty Images)

It was always a given that the Yankees would have to overpay to retain their captain and star shortstop. But Jeter wasn't just overpaid—he was given a blank check.

The future Hall-of-Famer had the worst season of his career in 2010 at the ripe age of 36. His batting average fell to .270 (career .314), his slugging percentage dropped to .370 (career .452) and he only hit 10 home runs, his lowest total since 2003.

If Jeter, or the Yankees for that matter, think that he's capable of returning to his career averages while approaching 40, then they have another thing coming.