The Most Embarrassingly Bad Free Agent Signing in the History of Each MLB Team

The playoff picture is shaping up with each passing day, but for many teams out of the race, it is time to evaluate their minor league talent and look ahead to the upcoming free agent class.

While developing players is an integral part of building a winner, the importance of making the most of your money in free agency can't be understated.

Just look at the Chicago Cubs, who have a talented core but are buried under the contracts of Alfonso Soriano, Carlos Zambrano, Ryan Dempster and Aramis Ramirez.

So what follows are the worst free agent signings in the history of each MLB team, and it should be noted that I only included players who joined new teams when signing their deals. So, awful re-signings such as Darren Dreifort, Vernon Wells and Bobby Higginson won't be on this list.

Feel free to suggest anyone I may have missed, and I look forward to your comments. Now, on with the list...

Arizona Diamondbacks: Russ Ortiz

Date: December 11th, 2004

Contract: Four Years, $33 Million

Stats: 5-16, 7.00 ERA, 67 Ks, 137.2 IP

Coming off of a 111-loss season, the Diamondbacks needed help in their rotation, and they thought they had found it in Ortiz, who was coming off a 15-win season with the Braves. He was 99-54 in the six seasons leading up to the signing.

However, he flopped horribly, going 5-11 with a 6.89 ERA in his first season in the desert. Then, he somehow managed to pitch worse the following season when he went 0-8 with an 8.14 ERA before being released in June of the 2006 season.

With two-and-a-half years and nearly $22 million left on his contract, his release marks what is believed to be the most expensive in baseball history, and the Diamondbacks truly got nothing out of this deal.

Atlanta Braves: Bruce Sutter

Date: December 7th, 1984

Contract: Six Years, $10 Million

Stats: 10-11, 40 Saves, 4.55 ERA, 6.4 K/9, 152.1 IP

When Sutter signed with the Braves before the 1985 season, he entered the season with a 2.54 career ERA and 260 career saves, and he was one of the premier relievers in all of baseball.

However, he was also turning 32 years old, meaning he would be 38 by the time the contract was up. He had a decent first season in Atlanta, posting a 4.48 ERA and 23 saves. However, injuries set in the next season, and after making just 16 appearances in 1986, he missed the entire 1987 season.

The 1988 season would be his last hurrah, as he retired following a 14-save, 4.76 ERA season with two years left on his contract that the Braves had to pay out. There is no doubt that Sutter is a Hall of Famer, but certainly not for his contributions with the Braves.

Baltimore Orioles: Albert Belle

Date: December 1st, 1998

Contract: Five Years, $65 Million

Stats: .289 BA, 60 HR, 220 RBI, 179 R

After a fantastic eight-year run with the Indians, Belle signed a five-year, $55-million contract with the White Sox prior to the 1997 season.

Included in the contract was an odd clause that allowed him to demand that he remained one of the three highest-paid players in baseball. When he invoked the clause prior to the 1999 season, the White Sox declined to give him a raise and he immediately became a free agent.

He then signed with the Orioles, but played just two more seasons before retiring due to a degenerative hip condition. The Orioles left him on the 40-man roster the remaining three seasons of his contract and managed to recoup some of the their losses, but it was still far from worth the price they paid for him.

Boston Red Sox: Matt Young

Date: December 4th, 1990

Contract: Three Years, $6.4 Million

Stats: 4-17, 5.01 ERA, 191 Ks, 233.2 IP

Coming off of an 18-loss season, and with a career line of 51-78 with a 4.26 ERA, Young was far from a front-of-the-rotation starter. But that did not stop the Red Sox from shelling out a surprising amount of money for the then 32-year-old.

The money didn't change much, as Young struggled through two seasons with the Red Sox before being released prior to the final season of his contract. He did, however, make history on April 12, 1992 when he pitched an eight-inning no-hitter but took the loss, walking seven and allowing six stolen bases and two runs.

You can make an argument that this spot belongs to Dice-K, but the Red Sox had the money to spend and they were aggressive enough to land a highly prized free agent when they signed him. The Dice-K signing may not have panned out, but it made a lot more sense at the time than the signing of Young did in 1991.

Chicago Cubs: Todd Hundley

Date: December 19th, 2000

Contract: Four Years, $23.5 Million

Stats: .199 BA, 28 HR, 66 RBI, 55 R

In theory, this was a solid move by the Cubs, as Hundley's father Randy was a Cubs legend and the team was in need of a catcher and middle-of-the-order bat, and Hundley seemingly provided both.

It couldn't have gone worse, as his first season goes down as one of the worst in baseball history. He hit .187 in 246 at bats and struck out 89 times, which amounts to once every 2.8 at-bats.

The next season was more of the same, and it is a miracle that the Cubs managed to cut their losses heading into the 2003 season when, for some reason, the Dodgers traded Eric Karros and Mark Grudzielanek to the Cubs for Hundley.

The Alfonso Soriano eight-year deal is no doubt a bad one, but he represented the best available player for a team looking to win now when he was signed, and he did help the team to a pair of playoff appearances.

Chicago White Sox: Jamie Navarro

Date: December 11th, 1996

Contract: Four Years, $20 Million

Stats: 25-49, 6.32 ERA, 303 Ks, 575.1 IP

After back-to-back impressive seasons with the Chicago Cubs, in which he went a combined 29-18 with a 3.62 ERA, Navarro inked a big contract in free agency that sent him to the South Side.

One troubling aspect of his final season with the Cubs was the fact that, despite his 15-12 record and 3.92 ERA, he gave up an NL-worst 244 hits, although he was able to wiggle out of trouble more times than not.

He would not be as lucky when it came to tight-roping around those hits when he got to the White Sox, however, as he led the AL with 267 hits allowed in his first season and struggled to a 9-14 record. It only got worse from there, as he went 8-16 and 8-13 with ERAs over 6.00 in his next two seasons.

He was eventually traded to Milwaukee in what turned out to be a great deal for the Sox, as they acquired Cal Eldred and Jose Valentin in the swap, but the signing was an awful one nonetheless.

Cincinnati Reds: Eric Milton

Date: December 28th, 2004

Contract: Three Years, $25.5 Million

Stats: 16-27, 5.83 ERA, 231 Ks, 370.1 IP

With a rotation that featured Juan Acevedo (5.94 ERA), Brandon Claussen (6.14 ERA), Cory Lidle (5.32 ERA), and Todd Van Poppel (6.09 ERA), there was little doubt what the Reds' most pressing need was in the 2004-05 offseason.

They made a move to pick up left-hander Eric Milton, who was coming off of a 14-win season with the Phillies. While Milton had an attractive 71-57 career record, he was also a fly-ball pitcher coming off a season in which he gave up a league-high 43 longballs.

That trend would continue in Great American Ballpark, as he again led the league with 40 home runs allowed in his first season with the Reds. However, the winning would not continue, as he went 8-15 with a 6.47 ERA. He was equally awful the next season, and was shelved after just five starts in his final season with the team.

Cleveland Indians: Wayne Garland

Date: November 19th, 1976

Contract: Ten Years, $2.3 Million

Stats: 28-48, 4.50 ERA, 241 Ks, 613.1 IP

The year was 1976, and it was the first offseason of wide-scale free agency in the big leagues. Garland was a 25-year-old starter coming off of a 20-7, 2.67 ERA, 113 K season with the Orioles, and he seemed primed to be the game's next big pitcher.

The Indians decided to lock Garland up while they could, signing him to a 10-year deal. He promptly led the American League in losses the following season when he went 13-19, and he was waived just five seasons and 28 wins into his mega deal.

Colorado Rockies: Mike Hampton

Date: December 12th, 2000

Contract: Eight Years, $121 Million

Stats: 56-52, 4.81 ERA, 458 Ks, 891.1 IP

After breaking out with a 22-win season in 1999, Hampton was the top free-agent arm when he hit the open market prior to the 2001 season.  The Rockies rewarded him with what was the largest contract in sports history at the time.

After an uninspired 14-13, 5.41 ERA, 122 Ks first season with the team, things only got worse for Hampton when he went 7-15 with a 6.15 ERA the next season. He was dealt to the Marlins and then Braves the following season, and while he was better, injuries limited him to just 85 more starts over the final six seasons of the deal.

Honorable mention to Denny Neagle who signed a five year, $51 million contract that same offseason and delivered a 19-23 record and 5.57 ERA over the span of the contract.

Detroit Tigers: Mike Moore

Date: December 9th, 1992

Contract: Three Years, $10 Million

Stats: 29-34, 5.90 ERA, 215 Ks, 500.2 IP

Coming off a fantastic four-year stretch with the Athletics in which he went 66-46 with a 3.54 ERA and helped the team to three playoff appearances, Moore was a hot commodity when he hit the free agent market prior to the 1993 season.

The Tigers open their wallets to add the 33-year-old veteran, and while he went 13-9 in his first season, his 5.22 ERA would be a sign of things to come.

The following season his ERA climbed to 5.42 and his record dipped to 11-10, as he led the AL in walks with 89 for a 5.2 BB/9 mark. The final season of the contract was easily the worst though, as he completely bottomed out with a 7.53 ERA and 5-15 record. His release in September would signal the end of his career.

Florida Marlins: Javier Vazquez

Date: December 2nd, 2010

Contract: One Year, $7 Million

Stats: 7-9, 4.72 ERA, 94 Ks, 127.2 IP

Through the years, the Marlins have been among the best in the business at making the most of their small market status with smart free agency moves.

In fact, they more or less bought their 1997 World Series title through good free agent moves, and while they had to tear the team apart shortly thereafter, they were the perfect mix of young players making nothing and veterans on short contracts.

With such a history of shrewd moves, that made the signing of Vazquez this past offseason an even bigger head scratcher. While it was only a one-year deal, he was coming off of a rough season in 2010, and it is not as though the Marlins were in a win-now position.

Houston Astros: Kaz Matsui

Date: November 30th, 2007

Contract: Three Years, $16.5 Million

Stats: .259 BA, 15 HR, 80 RBI, 118 R, 40 SB

Matsui picked the perfect time to have the best season of his career in 2007, as he posted a 4.1 WAR and helped the Rockies reach their first World Series just as he was set to hit the free agent market.

The Astros jumped at the chance to add the speedy second baseman, and he was solid in his first season with a .293 average and 20 stolen bases, although injuries limited him to just 96 games.

The following season, his average dipped to .250, but that was nothing compared to the final season of his contract when he hit just .141 through his first 71 at bats before being released on May 24th.

Kansas City Royals: Mark Davis

Date: December 11th, 1989

Contract: Three Years, $14 Million

Stats: 10-13, 7 Saves, 5.47 ERA, 154 Ks, 184.1 IP, 109 Appearances

Coming off of a Cy Young season with the Padres, when he posted a line of 4-3, 44 Saves, 1.85 ERA, 92 Ks, 92.2 innings pitched, Davis was by far the best reliever on the free-agent market in 1990.

That, by no means, meant that he was deserving of being the highest-paid player in the game, but the Royals made him just that when they outbid everyone for his services.

He promptly forgot how to pitch as he posted a 5.31 ERA and just seven saves through two-and-a-half seasons with the Royals before being dealt to the Braves.

Los Angeles Angels: Mo Vaughn

Date: December 11th, 1998

Contract: Six Years, $80 Million

Stats: .267 BA, 98 HR, 312 RBI, 233 Runs

There is little debate that Vaughn was one of the most-feared sluggers of the 1990s, and when he finally left the Red Sox, he still had plenty of pop left in his bat, as he averaged .276, 34 homers and 112 RBI in his first two seasons in Anaheim.

However, injuries set in in 2001 and he missed the entire season. From there, his weight spiraled out of control and the Angels were forced to cut their losses and deal him to the Mets for starter Kevin Appier.

Appier went on to help the Angels to a World Series, while Vaughn struggled through two seasons with the Mets before retiring at the end of 2003.

Honorable mention to the five year, $50 million contract that the team gave a 32-year-old Gary Matthews Jr. in 2007 for some strange reason.

Los Angeles Dodgers: Jason Schmidt

Date: December 6th, 2006

Contract: Three Years, $47 Million

Stats: 3-6, 6.02 ERA, 30 Ks, 43.1 IP, 10 Starts

After six seasons and 78 wins as a member of the Giants, Schmidt had established himself as one of the top pitchers in the game when he hit the free-agent market in 2007.

He was simply awful for the Dodgers, however, as the team officially paid $15.67 million per win and $4.7 million per start in what goes down as one of the least productive contracts in baseball history.

The Dodgers recent history is riddled with poor signings, with Juan Pierre (Five Years, $44 Million), Andruw Jones (Two Years, $36.2 Million) and Kevin Brown (Seven Years, $105 Million) coming to mind immediately.

Milwaukee Brewers: Jeff Suppan

Date: December 24th, 2006

Contract: Four Years, $42.5 Million

Stats: 32-42, 4.95 ERA, 335 Ks, 647.1 IP

From 1999-2006, Suppan established himself as one of the most durable pitchers in all of baseball, averaging 32 starts and 204 innings pitched over that span, while posting double-digits in wins seven times.

He was especially good with the Cardinals from 2004-2006, going 44-26 and winning the 2006 NLCS MVP, and so his stock was at its highest as he hit free agency prior to the 2007 season.

With his postseason heroics fresh in their mind, the Brewers paid him like an ace, but after going 22-22 in his first two seasons, Suppan only got worse. He was eventually relegated to the bullpen in 2010 before he was finally released.

Minnesota Twins: Sean Bergman

Date: October 12th, 1999

Contract: One Year, $1.2 Million

Stats: 4-5, 9.66 ERA, 35 Ks, 68 IP

The Twins have always been a small market team, and one that tends to prefer retaining homegrown talent to spending money in free agency.

For the 2000 season, their team payroll was a meager $15.7 million, and just four players on the team made over $1 million. For some reason, one of them was waiver claim acquisition Sean Bergman.

Coming off a season when he went 5-6 with a 5.21 ERA, and with a 4.84 career ERA, there was no reason to think that Bergman would be anything more than a fifth starter or long reliever, but he was the second highest paid pitcher on the roster, and he was simply awful.

New York Mets: Bobby Bonilla

Date: December 2nd, 1991

Contract: Five Years, $25 Million

Stats: .286 BA, 129 HR, 439 RBI, 406 R

After starring with the Pirates alongside Barry Bonds and Andy Van Slyke, Bonilla took his talents to The Big Apple in 1992, signing a contract that made him the highest-paid player in baseball at the time.

What followed was three-and-a-half seasons of mediocrity, as he hit well enough to make a pair of All-Star teams, but came far from justifying his status as the highest-paid player in the game. He was then dealt to the Orioles, with the remaining $5.9 million of his contract to be deferred until 2011 at eight percent interest.

While that freed up money for the Mets at the time, they now owe him a little over $29 million, which will be paid out at $1.19 million per year for the next 25 years, with the first payment being made this past July.

Just to put things in perspective, when the team makes its final payment on the deal, Bonilla will be 72 years old.

New York Yankees: Kei Igawa

Date: December 19th, 2006

Contract: Five Years, $20 Million (plus $26-million posting fee)

Stats: 2-4, 6.66 ERA, 53 Ks, 71.2 IP, 13 Starts

After losing out on the Daisuke Matsuzaka sweepstakes to the Boston Red Sox, the Yankees turned their attention to another Japanese pitcher in the then 27-year-old left-hander Igawa.

He bounced between the rotation, bullpen and minor leagues in his rookie season, going 2-3 with a 6.25 ERA. Sadly, that is actually his best season to date, as he made just two more big-league appearances since, posting a 13.50 ERA in four innings of work.

Rather than release him, the Yankees have him playing out his contract at Triple-A, where he has gone 33-22 with a 3.81 ERA in part of five seasons.

Oakland Athletics: Esteban Loaiza

Date: November 29th, 2005

Contract: Three Years, $21.4 Million

Stats: 12-9, 4.62 ERA, 102 Ks, 169.1 IP

Loaiza was a career journeyman when he signed with the White Sox before the 2003 season, at which time he broke out, going 21-9 and finishing second in AL Cy Young voting.

After the White Sox dealt him to the Yankees for Jose Contreras, Loaiza was still an effective starter in 2004, as well as the following season with the Nationals. That led the A's to ink him to an uncharacteristically large deal for GM Billy Beane, but at that point he was already 34 years old.

After an adequate 11-9, 4.89 ERA season in 2006, injuries set in and he was eventually waived and picked up by the Dodgers. After that, he was released twice in 2008, as his career came to an end.

Philadelphia Phillies: Adam Eaton

Date: November 27th, 2006

Contract: Three Years, $24 Million

Stats: 14-18, 6.10 ERA, 154 Ks, 268.2 IP

Once considered the better of the two Padres pitching prospects when he and Jake Peavy first entered the big leagues, Eaton got a big deal from the Phillies in 2006 despite a 5.12 ERA in 13 starts with the Rangers the previous season.

It would be more of the same for the big right-hander, as he went 10-10 in his first season in Philadelphia, but posted a terrible 6.29 ERA in 30 starts.

He was again awful the next season, going 4-8 with a 5.80 ERA, and he did not make it to the end of his contract, as he was released prior to the 2009 season.

Pittsburgh Pirates: Derek Bell

Date: December 10th, 2000

Contract: Two Years, $9.5 Million

Stats: .173 BA, 5 HR, 13 RBI, 14 R

After a productive career as a member of the Astros' "Killer B's," Bell hit free agency at the age of 31 in 2001 after being traded to the Mets in the Mike Hampton deal, and they chose to let him walk as he was clearly on the downside of his career.

Hoping he still had something left, the Pirates inked the slugger to a two-year deal. However, after an injury-shortened and highly-ineffective first season, Bell made waves in Spring Training prior to the 2002 season.

Upon learning that he would be competing for a starting job, Bell refused to be a part of it, stating that he hadn't competed for a spot since his rookie year and wouldn't do so now, choosing instead to go into "Operation Shutdown" as he called it. By the end of March, he was released, and he would never play in the majors again.

San Diego Padres: Oscar Gamble

Date: November 29th, 1977

Contract: Six Years, $2.85 Million

Stats: .275 BA, 7 HR, 47 RBI, 46 R

Coming off of a monster season with the White Sox in which he hit .297 with 31 HR and 83 RBI, Gamble was scooped up by the Padres in free agency, as the team inked him to a six-year deal.

However, after a subpar first season with the team, he was dealt along with $300,000 to the Rangers, who then traded him to the Yankees at mid-season.

He enjoyed a bounce-back season following the trade, and to make matters worse the Padres were on the hook for $750,000 in deferred salary on top of the $300,000 that they shipped to Texas along with him.

San Francisco Giants: Barry Zito

Date: December 29th, 2006

Contract: Seven Years, $126 Million

Stats: 43-61, 4.52 ERA, 583 Ks, 817.2 IP

With 102 wins, an AL Cy Young and one of the game's best curveballs to his credit, Zito was the 2007 offseason's top commodity, and he crossed the bay to the National League for what was then a record deal for a pitcher.

However, he left that curveball, along with that ability to win games, in Oakland, and he has yet to post a winning season five years into this mega deal.

To make matters worse, injuries have struck this season and he has been limited to just nine starts. That said, his injury opened things up for Ryan Vogelsong to get a chance, and considering Zito's 5.62 ERA over those nine starts, maybe it is for the best that he is on the disabled list.

Seattle Mariners: Carlos Silva

Date: December 20th, 2007

Contract: Four Years, $48 Million

Stats: 5-18, 6.81 ERA, 79 Ks, 183.2 IP

Coming off of a 13-14 season with the Twins, and with a line of just 47-45, 4.42 ERA, 306 Ks as a starter, the Mariners, for whatever reason, decided to pay Silva like a staff ace.

He responded with what was easily the worst season of any starting pitcher in 2008, as he posted a line of 4-15, 6.46 ERA, 69 Ks, 153.1 innings pitched. The following season was even worse, as he made just six starts, going 1-3 with a lofty 8.60 ERA.

Luckily for the Mariners, the Cubs were desperate to get rid of another awful contract in Milton Bradley, and they took on Silva, with the Mariners chipping in $9 million to sweeten the deal. Silva turned things around a bit last season, going 10-6, but he was released this past spring when he caused more than one distraction, and his career looks to be over.

St. Louis Cardinals: Kip Wells

Date: November 28th, 2006

Contract: One Year, $4 Million

Stats: 7-17, 5.70 ERA, 122 Ks, 162.2 IP

While there is a long list of Dave Duncan success stories, Wells is certainly not among them, as he was absolutely horrible in his one season with the Cards.

He had shown flashes of his talent as a member of the Pirates, winning double-digit games twice for some bad Pittsburgh teams, and he was still just 30 years old when signed with St. Louis.

Rather than enjoy a career renaissance as many do under the tutelage of Duncan, he was possibly the worst starter in baseball, and it is impressive in itself that he was able to make 26 starts before being relegated to the bullpen.

Tampa Bay Rays: Pat Burrell

Date: January 5th, 2009

Contract: Two Years, $16 Million

Stats: .218 BA, 16 HR, 77 RBI, 54 R

Coming off of a World Series win, Pat Burrell turned down a two-year, $22-million offer to remain with the Phillies, hoping to cash in on the open market. However, when he found that his stock was surprisingly low, he had to settle for a smaller contract from the Rays.

He then proceeded to completely forget how to hit, posting a .218 average, 16 homers, 77 RBI line in a season and a half with the team before he was eventually released.

The Giants, in need of an offensive spark, quickly signed Burrell, and he immediately turned things around, hitting 18 homers with 51 RBI in just 96 games—and all while being paid handsomely by the Rays.

Texas Rangers: Chan Ho Park

Date: January 16th, 2002

Contract: Five Years, $65 Million

Stats: 22-23, 5.79 ERA, 280 Ks, 380.2 IP

After winning 75 games in five seasons with the Dodgers from 1997-2001, Park was a hot commodity when he hit the market prior to the 2002 season, and the Rangers opened their wallets wide for the then 29-year-old.

He then proceeded to flop like few have flopped before, never posting an ERA under 5.00 in just over three seasons with the Rangers. After that, he was dealt to the Padres for another big contract in Phil Nevin, with the Padres paying the final season and $15 million of the deal.

Also worth mentioning is the record-breaking ten year, $252 million deal that the team signed Alex Rodriguez to. While his numbers were terrific, the team lost 89, 90 and 91 games in A-Rod's three seasons with the team.

Toronto Blue Jays: Erik Hanson

Date: December 22nd, 1995

Contract: Three Years, $9.4 Million

Stats: 13-20, 5.68 ERA, 195 Ks, 278.2 IP

After a string of subpar seasons, Hanson had trouble finding a suitor heading into the 1995 season, eventually signing a one year, $1.5 million deal with the Red Sox.

He made the most of that contract, going 15-5 and making the first and only All-Star appearance of his career. However, that masked the fact that he had a 4.24 ERA and 1.318 WHIP.

Still, it was enough to net the 31-year-old a three year deal with the Blue Jays, and in his first season he struggled to a 13-17 record with a bloated 5.71 ERA.

Sadly, that would be the best season of the three, as he made just 14 more appearances over the final two seasons of the deal, going 0-3 with a 6.61 ERA, as he was eventually released in June of 1998.

Washington Nationals: Jayson Werth

Date: December 5th, 2010

Contract: Seven Year, $126 Million

Stats: .223 BA, 13 HR, 43 RBI, 49 R, 14 SB

You could certainly say that it is too early to write off this deal as terrible, but this deal was a disaster before Werth ever took the field.

There is no doubt that Werth's contributions to the Phillies played a part in their success over the past several seasons, as his combination of power, speed and defense made him incredibly valuable.

That said, he is by no means a superstar, having never batted over .300 or driven in 100 runs, and never won a Gold Glove defensively. And at 32 years old, this deal will only get worse as the years pass.