2012 MLB Free Agency: 50 Most Disastrous Deals in MLB Offseason History

The offseason is often when teams go from contender to champion, as making the right trade or signing the right free agent can push a team over the top.

On the other end of the spectrum, though, a team's offseason transactions can sometimes put them back several seasons, whether it is by tying up a lot of money in a dud free agent, or dealing the next big thing for a washed-up veteran.

Sticking to that second category of transactions, here are the 50 most disastrous deals in MLB offseason history.

No. 50: Pirates Sign Derek Bell, 2001

Deal: Two Years, $9.5 Million

After a productive career as a member of the Astros' "Killer B's," Bell hit free agency at the age of 31 in 2001, and the Astros 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 would never play in the majors again.

No. 49: Mariners Trade Omar Vizquel to Indians, 1994

Deal: Reggie Jefferson, Felix Fermin, Cash to Mariners. Omar Vizquel to Indians.

Coming off the first Gold Glove of his career, Vizquel was already considered one of the top defensive shortstops in all of baseball, but with a .252 career average, the Mariners decided they could stand to trade him.

The Indians sent Reggie Jefferson, a 24-year-old DH with some power potential and Felix Fermin, an average all-around shortstop who could take Vizquel's place, to the Mariners. Neither did much in Seattle, and were not with the team two years later.

Vizquel soon became the Ozzie Smith of the American League, and his offense improved as well, and in 11 total seasons with the Indians, he hit .283 and stole 279 bases while capturing an impressive eight more Gold Gloves.

No. 48: Cubs Sign Todd Hundley, 2001

Deal: Four Years, $23.5 Million

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, striking out 89 times which amounts to once every 2.8 at-bats.

The next season was more of the same, and 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.

No. 47: Indians Trade Brian Giles to Pirates, 1999

Deal: Ricardo Rincon to Indians. Brian Giles to Pirates.

Ah, the prices a contender will pay for reliable middle relief. Giles was the odd man out in an outfield that consisted of David Justice, Kenny Lofton and Manny Ramirez, so he was shipped to Pittsburgh for Rincon.

After hitting combined 33 HR in just over 700 at bats between 1997 and 1998, Giles had the potential to be a major run producer, and he lived up to it immediately with a .315 BA, 39 HR, 115 RBI line in his first season with the Pirates.

In his four full seasons in Pittsburgh, Giles averaged .309 BA, 37 HR, 109 RBI, as he became one of the NL's premier sluggers.

When the time came to deal Giles, an inevitability for any good Pirates player of the past couple decades, the Pirates got maximum value netting Jason Bay and Oliver Perez from the Padres in what was another of the Pirates' better moves.

No. 46: Phillies Sign Adam Eaton, 2006

Deal: Three Years, $24 Million

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, and he did not make it to the end of his contract, as he was released prior to the 2009 season.

No. 45: Orioles Trade Curt Schilling, Steve Finley to Astros, 1991

Deal: Glenn Davis to Orioles. Curt Schilling, Steve Finley, Pete Harnisch to Astros.

After six successful seasons with the Astros in which Davis hit 164 home runs, the Orioles dealt three of their top young prospects to acquire the then 30-year-old slugger.

The move proved to be ill-advised, as Davis hit a combined .247 BA, 24 HR, 85 RBI over three seasons in Baltimore before retiring.

Meanwhile, the Astros got a starting center fielder in Finley who spent four seasons with the team and eventually became one of the game's top center fielders. They got a solid starting pitcher who won 45 games in his four seasons with the team and 111 over his 14-year career.

The big name of the deal, however, was Schilling and he spent just one season with the team before being traded to the Phillies. The big picture though is that the Orioles could have had all four of these players if they would have developed them rather than making this trade.

No. 44: Yankees Sign Hideki Irabu, 1997

Deal: Four Years, $12.8 Million

Irabu will always have a significant place in baseball history, as it was after his signing that the posting system was put in place that is currently used between the United States and Japan.

However, that is the only reason he will be remembered, as after a storied career in Japan from 1988-1996, he was just awful during his time in the States.

And when you are awful in New York, especially after you refuse to play for any other team as Irabu did, your struggles tend to be front-page news.

No. 43: Athletics Trade Andre Ethier to Dodgers, 2006

Deal: Milton Bradley, Antonio Perez to Athletics. Andre Ethier to Dodgers.

A second-round pick in the 2003 MLB Draft, Ethier was progressing quickly through the Athletics farm system and looked poised to make his big-league debut in Oakland in 2006.

However, the team instead decided to trade him to the Dodgers for veteran Milton Bradley, who was coming off of an injury-plagued .290 BA, 13 HR, 38 RBI season. Injuries struck again in Oakland, and he was limited to just 96 games in 2006 and 19 the following season before being traded to the Padres.

Ethier stepped right into the starting lineup in Los Angeles, hitting .308 BA, 11 HR, 55 RBI to finish fifth in Rookie of the Year voting. He has since developed into one of the game's top young outfielders and earned a reputation as one of the best clutch hitters in the game.

No. 42: Red Sox Sign Matt Young, 1991

Deal: Three Years, $6.4 Million

Coming off of an 18-loss season, and with a career line of 51-78, 4.26 ERA, 666 Ks, 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 make headlines on April 12, 1992, when he pitched an eight-inning no-hitter but took the loss as he walked seven and allowed six stolen bases and two runs.

No. 41: Marlins Trade Derrek Lee to Cubs, 2004

Deal: Hee-Seop Choi, Mike Nannini to Marlins. Derrek Lee to Cubs.

A little over a month after watching Lee advance past the Cubs and win a World Series with the Marlins, Lee joined the team he beat, and for what amounts to peanuts.

While he never quite fulfilled his potential in Florida, Lee was always a great fielder and a lock for 20 HR and 80 RBI, still far more than Hee-Seop Choi had ever proven to be capable of doing.

The once-top prospect of the Cubs hit a dismal .218 as the starter early on in the 2003 season. A collision with Kerry Wood ended his season and a platoon of Eric Karros and Randall Simon helped the Cubs make the playoffs in his absence.

Lee gave the Cubs stability at first base and in the middle of the order, hitting ..298 BA, 179 HR, 574 RBI in parts of seven seasons with the team, while Choi spent 90 games with the Marlins before he was traded to the Dodgers and he was out of the majors after 2005.

No. 40: Mets Sign Bobby Bonilla, 1992

Deal: Five Years, $25 Million

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 being the highest-paid player in the game. He was eventually traded to the Orioles for then-top prospect Alex Ochoa, who turned out to be quite the flop himself.

Adding to the contract, the Mets bought out the final $5.9 million of his contract but decided to defer payment until 2011, which, with interest, has turned into $29 million the Mets will be paying him for years to come.

No. 39: Devil Rays Trade Bobby Abreu to Phillies, 1998

Deal: Kevin Stocker to Devil Rays. Bobby Abreu to Phillies

With the sixth pick in the 1998 Expansion Draft, the newly formed Devil Rays selected 23-year-old outfielder Bobby Abreu from the Astros.

However, later that day they flipped him to the Phillies in return for shortstop Kevin Stocker, who would serve as their starting shortstop their inaugural season and hit all of .208 and was out of the league three years later at the age of 30.

Abreu immediately stepped into a starting role with the Phillies and hit .312 BA, 17 HR, 74 RBI, 19 SB in his first season of full-time action.

He would only get better from there, and in nine seasons in Philadelphia, he hit .303 BA, 195 HR, 814 RBI, 254 SB, including a pair of 30-30 seasons.

No. 38: Indians Sign Wayne Garland, 1977

Deal: 10 Years, $2.3 Million

The year was 1977, 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 one of the game's next big pitchers.

The Indians decided to lock Garland up while they could, signing him for 10 seasons. 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.

No. 37: Angels Trade Mike Napoli for Vernon Wells, 2011

Deal: Vernon Wells to Angels. Mike Napoli, Juan Rivera to Blue Jays.

Saddled by the awful seven-year, $126 million contract they gave Vernon Wells, the Blue Jays looked as though they would have little financial freedom until the deal was up at the end of 2014.

However, after the Angels missed out on signing Adrian Beltre and Carl Crawford, they were desperate to add some offensive punch and traded for Wells, taking on the remaining four years of his contract and receiving just $5 million to offset it.

The move was a head-scratcher from the onset, and Wells did little to justify it by hitting a whopping .218, and the Angels now have a logjam of washed up, overpaid outfielders in Wells, Torii Hunter and Bobby Abreu.

Meanwhile, the Blue Jays flipped Napoli to the Rangers for reliever Frank Francisco and he emerged as the top offensive catcher in all of baseball with a line of .320 BA, 30 HR, 75 RBI as he helped lead the Rangers to the World Series.

No. 36: Royals Sign Mark Davis, 1990

Deal: Three Years, $14 Million

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 relief pitcher 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 and struggled through two-and-a-half seasons with the Royals before being dealt to the Braves.

No. 35: Astros Trade Joe Morgan to the Reds, 1972

Deal: Lee May, Tommy Helms, Jimmy Stewart to Astros. Joe Morgan, Cesar Geronimo, Jack Billingham, Ed Armbrister, Denis Menke to Reds.

A two-time All-Star in nine seasons with the Astros, Joe Morgan was traded to a Reds team in desperate need of a second baseman for slugger Lee May in what seemed to be a great deal.

Morgan then proceeded to be an All-Star in all eight of his seasons in Cincinnati, serving as the catalyst of the Big Red Machine and for that he earned back-to-back NL MVP awards in 1975 and 1976.

May, on the other hand, spent just three seasons in Houston, averaging a solid if unspectacular line of .274 BA, 27 HR, 96 RBI before he was dealt again to the Royals, with the Astros getting nothing to speak of in return.

Morgan was not all the Reds got in the deal though, as Billingham went on to win 87 games with a 3.85 ERA in six years with the Reds as one of their best starting pitchers during the Big Red Machine era.

Geronimo was also the team's top outfielder off the bench, spending nine seasons with the team and posting a .261 average.

No. 34: Orioles Sign Albert Belle, 1999

Deal: Five Years, $65 Million

After a fantastic 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, however, left him on the 40-man roster for the remaining three seasons of his contract and managed to recoup some of their losses, but he still fell well short of expectations and cost the team a good deal of money.

No. 33: Cubs Sign Alfonso Soriano, 2007

Deal: Eight Years, $136 Million

Soriano has been productive as a member of the Cubs since joining the team, so he was not an entire wash like the many others towards the top of this list. That makes it hard to peg just how bad this signing should be considered.

Coming off of an amazing .277 BA, 46 HR, 95 RBI, 41 SB season with the Nationals, Soriano was the prize of the 2007 offseason, and the Cubs made him one of the richest players in the history of the game.

While he managed to make the All-Star team in his first two seasons in Chicago, he was hardly the player he once was, as he no longer stole bases as frequently and struggled to top 30 homers.

Now five years through the contract, Soriano is certainly not getting any better and seems to be as immovable as any player in the majors. This one could continue to creep up this list over the next three years, as he will be 38 years old by the time the deal is up.

No. 32: Giants Trade Joe Nathan for A.J. Pierzynski, 2004

Deal: A.J. Pierzynski to Giants. Joe Nathan, Francisco Liriano, Boof Bonser to Twins.

With a line of .312 BA, 11 HR, 74 RBI with the Twins in 2003, Pierzynski established himself as one of the top catchers in baseball. However, with Joe Mauer on the way, he became expendable in Minnesota and the Giants made a big offer to acquire him.

Pierzynski did his part on the field in 2004, hitting .272 with 11 HR and 77 RBI. However, he clashed with teammates and coaches in the clubhouse, and despite all they gave up to get him, the Giants released him after just one season with the team.

Nathan became one of the best closers in all of baseball, saving 260 games in seven seasons with the team.

Liriano has had an up-and-down career, and has a 47-42 record with a 4.19 ERA through six seasons with the Twins.

Bonser was a bottom-of-the-rotation guy, winning 18 games in three seasons with the Twins.

No. 31: Mariners Sign Carlos Silva, 2008

Deal: Four Years, $48 Million

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 went 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.

Heading into 2010, the Cubs and Mariners swapped awful contracts as the Mariners moved Silva and $9 million for Milton Bradley.

Silva contributed in Chicago with a 10-6 season in 2010, but made waves last spring when he did not make the rotation and was eventually released.

No. 30: Cubs Sign Milton Bradley, 2009

Deal: Three Years, $30 Million

Always a prickly personality when it comes to his presence in a clubhouse, the Cubs took a chance on Bradley in 2009, as he was coming off the best season of his career after hitting .321 BA, 22 HR, 77 RBI with the Rangers and leading the AL with a .436 OBP.

However, he slumped badly to open the season and never recovered, sparking a number of ejections and eventually being sent home for the season due to his attitude. The following offseason, the Cubs traded terrible contracts with the Mariners as they took on Carlos Silva's deal.

This past year, he lasted until just May 16, when the Mariners had finally had enough and released him, likely ending the 33-year-old's career.

No. 29: Tigers Trade Jim Bunning to Phillies, 1964

Deal: Don Demeter, Jack Hamilton to Tigers. Jim Bunning, Gus Triandos to Phillies

After spending the first nine years of his career with the Tigers and winning 118 games, Bunning was dealt to the Phillies at the age of 32 coming off a down season.

He bounced back nicely, though, as he won 74 games in his four seasons in Philadelphia before being traded to the Pirates for Don Money, in what was another solid move.

In return, the Tigers got slugging outfielder Dom Demeter, who was coming off of three straight 20-HR seasons, but after two decent seasons, he dropped off and he was out of baseball by 1967 at just 32 years old.

No. 28: Angels Sign Gary Matthews Jr., 2007

Deal: Five Years, $50 Million

After spending much of his career as a backup, Matthews finally got a chance to play every day during the 2005 season for the Rangers. After a solid season, he broke out the following year with a .313 BA, 19 HR, 79 RBI, 10 SB line in what was a contract year.

The Angels took a chance on the then-32-year-old's breakout season not being a fluke, giving him a massive contract despite his thin track record.

After an adequate first season in which he hit .252 BA, 18 HR, 72 RBI, Matthews became an offensive liability and he was dealt to the Mets prior to the 2010 season, but was released by the middle of June.

He spent the remainder of the season in Class-AAA for the Reds and did not play in 2011, all the while earning $12 million, of which $10.9 million came from the Angels.

No. 27: Rangers Sign Chan Ho Park, 2002

Deal: Five Years, $65 Million

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 three-and-a-half 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 and getting similar results.

No. 26: Browns Trade Roy Sievers to Senators, 1954

Deal: Gil Coan to Browns. Roy Sievers to Senators.

Roy Sievers looked to be the next big slugger when he captured AL Rookie of the Year honors in 1949 with a line of .306 BA, 16 HR, 91 RBI. Injuries took their toll after that season, though, as he managed to appear in just 247 games total over the next four years.

Having effectively given up on him, the Browns dealt Sievers to the Senators for middling outfielder Gil Coan, who spent a season and a half with the team, and was out of baseball two years later.

Sievers, on the other hand, finally managed to stay healthy and blossomed into one of the league's top hitters and in six seasons in Washington he hit .267 BA, 180 HR, 574 RBI. His best season came in 1957, when he hit .301 BA, 42 HR, 114 RBI, leading the league in HR, RBI and total bases.

No. 25: Marlins Trade Johan Santana to Twins, 2000

Deal: Jared Camp to Marlins. Johan Santana, Cash to Twins

A shining example of why the Rule 5 Draft exists, Santana never got a chance in Houston and was taken by the Marlins in the December draft, who then turned around and traded Santana along with some cash for the legendary Jared Camp.

After spending his first three seasons in Minnesota primarily as a reliever, Santana broke out with a 12-3 record as a swingman in 2003 when he made 45 appearances, 18 of which were starts.

The next season, he was inserted in the rotation full-time and he responded with a 20-6, 2.61 ERA, 265 K season that saw him take home his first of two Cy Young Awards.

Santana quickly became one of the game's top pitchers, and he won 93 games in eight seasons with the Twins before he was traded to the Mets for a group of prospects.

No. 24: Dodgers Sign Andruw Jones, 2008

Deal: Two Years, $36.2 Million

One of the best power hitters in all of baseball as recently as 2006, few falls from grace have been as swift as that of Andruw Jones.

After a poor showing in his final season in Atlanta, the Dodgers took a chance on his fall-off being a fluke, and signed him for top dollar.

He then proceeded to show up to spring training 20 pounds overweight, and he struggled mightily at the plate the entire season, hitting just .158 in 209 at-bats.

He was released at the end of the 2008 season, but he has enjoyed a bit of a career resurgence of late as a power bat off the bench for the White Sox and most recently the Yankees.

No. 23: Astros Trade Mike Cuellar to Orioles, 1969

Deal: Curt Belfary, John Mason to Astros. Mike Cuellar, Enzo Hernandez, Elijah Johnson to Orioles.

After opening his career by winning the AL Rookie of the Year for the Orioles in 1965, with a line of .260 BA, 22 HR, 70 RBI, Curt Belfary had posted similar numbers over the next two seasons before slumping in 1968.

In need of pitching, the Orioles dealt Belfary to the Astros for 32-year-old left-hander Mike Cuellar. In six big league seasons, Cuellar had been average at best with a career record of 42-41 with a 2.97 ERA.

However, he took off once he reached Baltimore as he went 23-11 with a 2.38 ERA to earn AL Cy Young honors and finish eighth in MVP voting. He would win at least 18 games in each of his first six seasons with the Orioles, going a combined 125-63 with a 2.99 ERA.

Belfary spent just one season with the Astros before being traded again to the Yankees, and he would never regain his early-career form.

No. 22: Diamondbacks Sign Russ Ortiz, 2005

Deal: Four Years, $33 Million

Fresh off of a fantastic two-year stint with the Braves in which Ortiz won 36 games, including an NL-best 21 in 2003, Ortiz was among the best starting pitchers available in the 2005 offseason.

Looking to rebuild after a terrible 111-loss season, the Diamondbacks hoped they had found their ace in Ortiz, but it was not to be.

After a rib injury shortened his first season in the desert to just 22 starts and an awful 5-11, 6.89 ERA mark, things only got worse the following season.

After starting the year 0-5 with a 7.54 ERA in six starts, the Diamondbacks cut Ortiz with $22 million left on his contract in what is one of the most expensive buyouts in baseball history.

No. 21: Tigers Trade Billy Pierce for Aaron Robinson, 1949

Deal: Aaron Robinson to Tigers. Billy Pierce, $10,000 to White Sox.

With the Tigers looking for a starting catcher heading into the 1949 season, they found a trade partner in the Chicago White Sox. Coming off of a 101-loss season, the White Sox had a lot of work to do, and had little use in the long-term for a 33-year-old former All-Star catcher.

So they sent Robinson to the Tigers, where he put up solid numbers in 1949 with a line of .269 BA, 13 HR and 56 RBI. However, he was out of the league two seasons later after falling off significantly after the 1949 campaign.

In return for Robinson, the White Sox got a 21-year-old left-hander named Billy Pierce who had just 27 big league appearances and five starts under his belt. He would immediately join the White Sox rotation, going on to win 186 games with a 3.19 ERA in 13 seasons on the South Side.

The fact that the Tigers threw $10,000 into the deal for the White Sox is salt in the wound, as they gave up one of the best pitchers of the 1950s, and paid someone to take him off their hands.

No. 20: Dodgers Sign Darren Dreifort, 2001

Deal: Five Years, $55 Million

Coming off of a solid 12-9, 4.16 ERA, 164 K season in 2000, the Dodgers decided that the 28-year-old Dreifort was a big part of their future and locked him up with a five-year deal despite a career record of 39-45 with a 4.28 ERA to that point in his career.

Go figure that didn't work out well, as he went 4-7 with a 5.13 ERA in the first season of the contract before being shut down in July and undergoing surgery that would keep him out all of the 2002 season.

He returned to make 10 adequate starts in 2003 before moving to the bullpen in 2004, where he had his most productive season as the seventh-inning setup man appearing in 60 games with a 4.44 ERA and 11.2 K/9 mark. He would miss all of 2005 with an injury as well, and that was the end of his illustrious career.

No. 19: Athletics Trade Roger Maris to the Yankees, 1960

Deal: Hank Bauer, Don Larson, Norm Siebern, Marv Throneberry to Athletics. Roger Maris, Kent Hadley, Joe DeMaestri to Yankees.

Originally a member of the Indians, Roger Maris was traded to the Athletics in 1958 and was an All-Star in his first full season with the team the following year.

Despite that, he was traded again in 1960 when the A's sent him to the Yankees in a seven-player deal and while the big names of the deal were Hank Bauer and Don Larsen, it was Norm Siebern who was the prize of the trade as he hit a combined .289 BA, 78 HR, 367 RBI in three and a half seasons with the A's.

Maris thrived in New York, as he won the AL MVP with a line of .283 BA, 39 HR, 112 RBI in his first season and then followed that up with his legendary 61 home run season in 1961, capturing his second straight MVP.

In total, Maris played seven seasons with the Yankees and hit .265 BA, 203 HR, 547 RBI and helped the Yankees to five pennants and two titles. His historical significance and 1961 season move him up this list, as the A's no doubt regretted that move each day that season.

No. 18: Angels Sign Mo Vaughn, 1999

Deal: Six Years, $80 Million

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, 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.

No. 17: Dodgers Trade Pedro Martinez for Delino DeShields, 1994

Deal: Delino DeShields to Dodgers. Pedro Martinez to Expos.

With the departure of Jody Reed, the Dodger found themselves in need of a starting second baseman heading into the 1994 season, and they landed a dynamic speed threat in the Expos' Delino DeShields.

Still just 24 years old, DeShields had stolen 187 bases in four seasons in the league, while posting a respectable .277 average. However, he struggled to a .250 average and stole just 27 bases in his first year with the Dodgers and spent only three seasons with the team.

In return, the Expos got 22-year-old Pedro Martinez, who was arguably the best middle reliever in baseball the previous season when he went 10-5 with a 2.61 ERA and 119 Ks in 107 innings. However, he was wild and it was unclear whether he would be a starter down the road.

That was quickly cleared up though when the Expos plugged him into the rotation to open the 1994 season and he went 11-5 with a 3.42 ERA.

He would only get better, culminating in an NL Cy Young Award in his final season with the team in 1997 when he went 17-8 with a 1.90 ERA, 305 Ks and a whopping 13 complete games.

No. 16: Dodgers Sign Kevin Brown, 1998

Deal: Seven Years, $105 Million

After helping the Padres to an improbable World Series run in 1998, Brown hit the free-agent market and became baseball's first $100 million player, as the Dodgers offered Brown nearly $40 million more than anyone else that pursued him.

Brown won 31 games in his first two seasons in Los Angeles, but injuries struck and his production fell off the following two seasons as he was limited to just 29 starts.

He did manage to follow that up with a 14-9, 2.39 ERA, 185 K season in 2003, enough to spark some interest from the Yankees, and the Dodgers dealt the then-39-year-old for Jeff Weaver and cash.

In two seasons with the Yankees, Brown earned $31.4 million to go 14-13, 4.95 ERA in 35 starts and his time in New York may be best remembered for when he broke his hand punching a clubhouse wall, ending his 2004 season.

No. 15: Senators Trade Early Wynn to Indians, 1949

Deal: Eddie Robinson, Joe Haynes, Ed Klieman to Senators. Early Wynn, Mickey Vernon to Indians.

After eight up-and-down seasons with the Senators that included an 18-win season as well as a 17-loss season, Wynn was dealt to the Indians.

After a decent 11-7 first season in Cleveland, Wynn rattled off seven straight seasons with at least 17 wins, topping the 20-win plateau four times.

In all, Wynn recorded 163 wins with the Indians before being traded to the White Sox. However, he did re-join the Tribe in 1963 at the age of 43, winning one game to give him exactly 300 for his career.

On the other side of things, the Senators got an All-Star season out of Robinson in 1949 before he slumped and was traded the next season, while the other two players did nothing of note.

No. 14: Rockies Sign Denny Neagle, 2001

Deal: Five Years, $51 Million

After an impressive run with the Braves in which Neagle went 38-19 in three seasons, including a dazzling 20-5 campaign in 1997, Neagle was traded twice in the span of three years before becoming a free agent prior to the 2001 season.

Thinking he could reclaim some of his Braves magic and that his ground-ball approach would play well in Colorado, the Rockies inked Neagle to a massive contract.

After three seasons and 19 wins, Neagle missed all of 2004 with injury, and then was arrested for soliciting prostitution in 2005, marking the end of his baseball career. The Rockies were able to recover his 2005 salary due to his legal issues.

No. 13: Athletics Trade Jimmie Foxx to Red Sox, 1936

Deal: Gordan Rhodes, George Savino, $150,000 to Athletics. Jimmie Foxx, Johnny Marcum to Red Sox.

One of the greatest sluggers in baseball history, Foxx joined the Red Sox at the age of 28 after 11 stellar seasons with the Athletics in which he won two MVP Awards and three home run crowns, among other impressive accolades.

However, the A's had posted three straight losing seasons and were coming off their worst season yet with a 53-100 record.

The $150,000 the Athletics received in the trade helped owner Connie Mack pay the salary of some of his other highly paid stars at the height of the Great Depression, as he hoped to move Foxx when his value was highest and his production was set to decline.

Foxx didn't lose a step though, with six more top-tier seasons as a member of the Red Sox, compiling a line of .320 BA, 222 HR, 788 RBI in his time in Boston.

The Athletics continued to struggled even with the freed up payroll, and did not post a winning season following the trade until 1947.

No. 12: Dodgers Sign Jason Schmidt, 2007

Deal: Three Years, $47 Million

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.

No. 11: Phillies Trade Ryne Sandberg for Ivan DeJesus, 1982

Deal: Ivan DeJesus to Phillies. Larry Bowa, Ryne Sandberg to Cubs.

After spending 12 seasons with the Phillies, shortstop Larry Bowa was looking for an extension that would allow him to finish out his career with the team, but at 35 years old and with declining numbers, the Phillies had other ideas.

They found a taker for the veteran in the Cubs, who offered up 27-year-old Ivan DeJesus in return. Originally a Dodgers farm hand, DeJesus had shown promise since joining the Cubs in the trade that also brought Bill Buckner to the Cubs.

Because DeJesus still had some upside, the Cubs also landed a third-base prospect in the deal in the form of 22-year-old Ryne Sandberg.

The Cubs immediately plugged Sandberg into the starting lineup, moved him to second base, and two seasons later he was the NL MVP after leading the Cubs to the playoffs.

He would finish his career as one of the best second basemen ever to play the game with an offensive line of .285 BA, 282 HR and 1,061 RBI to go along with nine Gold Gloves.

No. 10: Yankees Sign Kei Igawa, 2007

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

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, signing him prior to the 2007 season.

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.

The Yankees have declined to release him, instead letting him play out his contract in the minor leagues. The NY Times had a very good article on him, profiling "The Lost Yankee."

No. 9: Yankees Sign Carl Pavano, 2005

Deal: Four Years, $39.95 Million

After a breakout season in 2004 with the Marlins when Pavano went 18-8, 3.00 ERA, 139 Ks and finished sixth in NL Cy Young voting, the right-hander cashed in at the expense of the Yankees.

After starting his Yankees career 4-2 with a 3.69 ERA in his first 10 starts, Pavano injured his elbow, which was the beginning of the end for his Yankees career, as he did not pitch at all in 2006 and made just nine starts in 2007 and 2008 combined.

No. 8: Mets Trade Nolan Ryan for Jim Fregosi, 1972

Deal: Jim Fregosi to Mets. Nolan Ryan, Don Rose, Frank Estrada, Leroy Stanton to Angels.

While he would go on to become one of the most dominant pitchers in baseball history, the career of Nolan Ryan began with a good deal of uncertainty stemming from his control problems.

After posting a record of 29-38 and walking over six batters per nine innings in his five seasons with the Mets, the team finally decided to trade him to the Angels for six-time All-Star shortstop Jim Fregosi.

Ryan immediately figured things out upon arriving in California, going 19-16, 2.28 ERA, 329 Ks, and he would go on to win 138 games with a 3.07 ERA in eight seasons with the Angels.

Fregosi on the other hand was disastrous, hitting .233 BA, 5 HR, 43 RBI in 146 games over parts of two seasons before he was sold to the Rangers.

No. 7: Red Sox Sign Daisuke Matsuzaka, 2007

Deal: 6 Years, $52 Million (plus $51-million posting fee)

Never has there been a more hyped-up signing of a foreign player than the media circus that surrounded the Red Sox acquisition of Dice-K prior to the 2007 season.

After winning the rights to negotiate with Dice-K following a $51 million posting fee, the Red Sox locked him up for six seasons. The early returns were promising, as he went 15-12 in his rookie season, then followed that up with a terrific 18-3, 2.90 ERA, 154 K line that earned him a fourth-place AL Cy Young finish.

However, injuries have limited him to just 44 starts the past three seasons, and he has been largely ineffective when healthy, going 16-15 with a 5.03 ERA.

He is in the final year of the deal, and due to make $10 million—it will be interesting to see what comes of Dice-K once he hits free agency.

No. 6: Cardinals Trade Steve Carlton for Rick Wise, 1972

Deal: Rick Wise to Cardinals. Steve Carlton to Phillies.

There is no question that Steve Carlton was a good pitcher from the start of his career, as he posted a 57-53 record in his first six seasons in the league with a terrific 2.98 ERA.

However, when he followed up a 1970 season in which he led the NL with 19 losses by going 20-9 in 1971, the Cardinals decided to deal the then 26-year-old when his value seemed to have peaked.

In return, the got another 26-year-old in Wise who was coming off of a 17-win season and had won 45 games in the past three seasons. He would go on to win 16 games in each of his two seasons with the Cardinals before they flipped him to the Red Sox for Reggie Smith and Ken Tatum.

Carlton, on the other hand, would go on to be one of the best pitchers of the 1970s, starting things out with a 27-10 record, 1.97 ERA and 310 Ks in his first year in Philadelphia, winning the pitching Triple Crown and the first of four NL Cy Young Awards.

With 329 career wins and 4,136 strikeouts, Carlton is a Phillies icon and is arguably the best left-hander to ever toe the rubber.

No. 5: Rockies Sign Mike Hampton, 2001

Deal: Eight Years, $121 Million

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, and 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 K first season with the team, things only got worse for Hampton, and he was dealt to the Braves prior to the 2003 season. After a pair of solid seasons in Atlanta, injuries set in, and Hampton made just 25 total starts from 2005-2008, missing all of 2006 and 2007.

No. 4: Reds Trade Frank Robinson for Milt Pappas, 1966

Deal: Milt Pappas, Jack Baldschun, Dick Simpson to Reds. Frank Robinson to Orioles.

Looking to bolster the team's pitching rotation, Reds GM Bill DeWitt made the controversial decision to deal superstar Frank Robinson to the Orioles for Milt Pappas, stating that Robinson was "an old 30" to try to justify the move.

It didn't take long for DeWitt to eat his words, as Robinson won the AL Triple Crown in his first season with the Orioles, hitting .316 with 49 HR and 122 RBI, leading the team to a World Series title in the process.

He would play a total of six seasons with the Orioles, hitting .300 with 179 HR and 545 RBI, showing that he was far from washed up at the age of 30, and cementing his place as one of the best hitters to ever play the game.

Pappas went 12-11 with a 4.29 ERA in his first season with the Reds, and 30-29 with a 4.04 ERA overall in parts of three seasons with the team before he was traded to the Braves.

Neither Baldschun nor Simpson did much of anything for the Reds, and they were out of Cincinnati by the end of the 1967 season.

No. 3: Giants Sign Barry Zito, 2007

Deal: Seven Years, $126 Million

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.

He made just nine starts this past season, along with four relief appearances. At this point, the Giants would almost be better off releasing him and eating the remaining two years of his contract.

No. 2: Reds Trade Christy Mathewson for Amos Rusie, 1901

Deal: Amos Rusie to Reds. Christy Mathewson to Giants.

Coming off of a poor season in which they went 62-77, the Reds addressed their most glaring need in the off-season leading up to the 1901 season, trading for veteran starter Amos Rusie.

Rusie had 246 career wins and would one day be a Hall of Famer, but he had not pitched in two seasons and was 30 years old at the time of the deal.

In the end, he would do little to solve the Reds' pitching woes, appearing in just three games and posting an 8.59 ERA in 22 innings of work for the Reds before retiring.

Normally, trading for a 30-year-old future Hall of Famer—even if he has not pitched in two seasons—is worth the risk. In this case though, the Reds gave up one of the greatest pitchers in baseball history, sending 20-year-old Christy Mathewson to the Giants in return for Rusie.

Mathewson had appeared in just six games the previous season, with an 0-3 record and a 5.08 ERA. That would all change quickly though, as he went 20-17 with a 2.41 ERA in his first season with the Giants.

In all, he would win 373 games and post a minuscule 2.13 ERA over his 17-year career.

No. 1: Red Sox Sell Babe Ruth to Yankees, 1920

Deal: $100,000 to Red Sox. Babe Ruth to Yankees.

It was the off-season following the 1919 baseball season, and the Red Sox had a full-blown superstar on their hands in Babe Ruth. Formerly a pitcher who could really hit, Ruth was now an outfielder who occasionally pitched, and he was putting up numbers that no one had ever seen before.

With a batting line of .322 BA, 29 HR and 114 RBI, and a pitching record of 9-5 with a 2.97 ERA over 133.1 innings, it was a season for the ages.

Whether it was Ruth asking for his salary to be doubled to $20,000, or whether the stories that Red Sox owner Harry Frazee was trying to finance a theatrical production were in fact true, for one reason or another, Ruth was put on the trade block.

The White Sox offered up $60,000 and "Shoeless" Joe Jackson for Ruth, but Frazee declined and instead took the Yankees' deal and the full $100,000 that he was seeking.

Thus, the Curse of the Bambino was born, as the Red Sox would go without a World Series until the curse was broken in 2004. Meanwhile, the Yankees became baseball's most revered franchise and piled up titles with Ruth leading the way.