MLB Free Agency: Every Team's Biggest Offseason Regret of All Time

Looking through the annals of baseball history, each team has its high and low points during the offseason.  The Boston Red Sox made a great deal in trading for Adrian Gonzalez, but could it overshadow the overpaying of John Lackey?  The same can be said for the New York Yankees, who despite acquiring an excellent outfielder in Curtis Granderson made a big free agency blunder in signing Carl Pavano (pictured), but more on that later.

Anyway, before I start rambling, let me get to the point.  Every regretful move a team makes during the offseason is different.  One may just be a small bump in the road, and the other may cause long-term damage that seems irreparable.

That being said, let's have a look at each team's biggest offseason regret of all-time.

Arizona Diamondbacks: The Wally Backman Fiasco

In the 2004 offseason, the Arizona Diamondbacks were looking for a new manager following a year that ended with a 51-111 record.  On November 1, they announced the hiring of former major league infielder Wally Backman, who had managed the team's High-A minor league team to an 86-54 record and had been named Minor League Manager of the Year.

However, the union was short-lived.  Just one day later, several reports surfaced about Backman's criminal and financial history.  He had been arrested for DUI in 1999 and had also declared bankruptcy to avoid paying over twenty creditors.

Since Backman had not disclosed this information to the Diamondbacks, he was let go just four days after being hired.  This didn't affect the franchise long term, but is a black mark on its history nonetheless.

Atlanta Braves: Losing Leo Mazzone

From 1990-2005, Leo Mazzone was the pitching coach for the Braves.  Under his tutelage, the team had a dominant pitching staff in the '90s that featured Tom Glavine, John Smoltz, Steve Avery and Greg Maddux.  Together, these four won a combined total of six NL Cy Young Awards in the 1990s as the Braves won the NL Eastern Division title every year from 1991-2005, making five trips to the World Series, winning once.

Yet, prior to the 2006 season, Mazzone signed a three-year contract to be the pitching coach for the Baltimore Orioles, for whom his best friend Sam Perlozzo was manager.  Mazzone did not fare as well in Baltimore, being fired after two seasons in which the Orioles finished in fourth place.

Seeing as how the Braves have another core group of young pitchers on the team right now, there's no telling how good they all could have been with Mazzone coaching them.

Baltimore Orioles: Trading for Sammy Sosa

It's no secret that for the past 14 years, the Baltimore Orioles have been trying to get over one giant hump.  To add insult to injury, every time they seem to be getting over said hump, they slide back down to the bottom.  Sure enough, this period of futility has seen some offseason moves that are just plain regretful.

Baltimore's occurred in 2005, when they traded popular utility man Jerry Hairston, Jr., infielder Mike Fontenot and pitcher Dave Crouthers to the Chicago Cubs for legendary slugger Sammy Sosa.  In doing so, the team had two members of the 500 home run club in their lineup: Sosa and first baseman/DH Rafael Palmeiro.

Unfortunately, Sosa had been on the decline for a few years at that point and in 2005, he posted his worst offensive numbers since 1992.  In 102 games, he hit just .221 with 14 home runs and just 45 RBI, pretty much confirming any suspicions that he may have used PEDs.

The team finished in fourth place Sosa's lone year with them and are still struggling to become a contender again.

Boston Red Sox: Trading the Bambino

In the early 1900s, the Boston Red Sox were one of the best teams in baseball.  Prior to 1920, the team had won five World Series titles: in 1903, 1912, 1915, 1916 and 1918.  One of the team's more popular players was George Herman "Babe" Ruth, who had made a name for himself as a pitcher the first few years of his career before his powerful bat turned him into a full-time outfielder.

Despite his popularity, Ruth was the victim of what has become, quite possibly, the worst decision in baseball history.  Though many believe that Red Sox owner Harry Frazee traded Ruth for cash to finance a Broadway play he was producing, the story is more realistic.

In reality, Ruth was demanding a $20,000 salary for the 1920 season, double what he made in 1919.  Frazee refused to pay that much, and Ruth stated that he would not play unless he received his raise.  Thus, Frazee's hands were tied.

Ultimately, Ruth was traded to the New York Yankees for $100,000 ($1.1 million today) and once he was on the team, the team went on to become the most successful franchise in baseball history.  The Red Sox, on the other hand, did not win another World Series for another 86 years and have since become the Yankees' most hated rivals.

If the trade hadn't happened, then perhaps the Red Sox wouldn't have had such a long playoff drought.

Chicago Cubs: Signing Alfonso Soriano

Having not won the World Series since 1908, not to mention not having even been that far since 1945, the Chicago Cubs are no strangers to misfortune.  There are so many bad offseason decisions I could choose, but I feel the one that stands out the most is when team management signed outfielder Alfonso Soriano prior to the 2007 season.

Soriano had spent the 2006 campaign with the Washington Nationals and had an All-Star year, batting .277 with 46 home runs, 95 RBI and 41 steals, becoming just the fourth member of the exclusive 40-40 Club.  This prompted the Cubs to give him an eight-year deal worth $136 million.

Since coming to Chicago, however, Soriano has become another bad contract doled out by ex-GM Jim Hendry.  His time in the Windy City has been marred by injury, shoddy defense and general decline.  The past three seasons, he has hit just .248.

Oh well.  Only three years and $51 million to go!

Chicago White Sox: Adam Dunn

Last offseason, the White Sox signed Adam Dunn to a four-year deal worth $56 million.  GM Kenny Williams hoped that Dunn would provide some much-needed pop to the lineup along with some protection in the lineup for first baseman Paul Konerko.

Instead, the new DH on the South Side had one of the worst offensive seasons in baseball history.  In 122 games, he hit just .159 with 11 home runs and 42 RBI.

Barring a major turnaround in 2012, this will easily be the team's biggest offseason regret in its entire history.

Cincinnati Reds: Hiring Dick Wagner as GM

In the 1970s, the Cincinnati Reds were one of the most dominant teams in the National League.  From 1970-1979, the squad known as "The Big Red Machine" went to the World Series four times and won back-to-back championships in 1975 and 1976.  With stars like Pete Rose, Johnny Bench and Ken Griffey, the team seemed unstoppable.

However, in 197, the Reds replaced Bob Howsham, the man who put that team together.  He was replaced by Dick Wagner, and the house fell down.

Not only did Wagner fire beloved manager Sparky Anderson after the 1978 season, but he completely dismantled the team.  His worst decision was easily letting star hitter Pete Rose go to the Philadelphia Phillies via free agency, and that could be the biggest offseason regret itself.

Yet, such a thing surely would not have happened had Wagner never been handed the reins.  He was fired in 1983 and Howsham replaced him, cleaning up his mess.

Cleveland Indians: The Wayne Garland Deal

In 1976, 25-year-old Wayne Garland had a phenomenal season for the Baltimore Orioles.  The right-hander went 20-7 with a 2.67 ERA, throwing 14 complete games.

Sure enough, once he entered free agency at season's end, he received some big offers.  He ended up signing a contract with the Cleveland Indians, a 10-year deal worth $2.3 million, to be exact.

In a classic case of overpaying for an average pitcher, Garland underachieved.  He went 13-19 with a 3.60 ERA in the first year of the deal and arm problems forced him to retire at age 30 in 1981.  With five years remaining on the deal, Garland went just 28-48 with a 4.50 ERA.

The team would not contend again until the 1990s.

Colorado Rockies: Signing Mike Hampton

Mike Hampton was a key member of the 2000 New York Mets team that made it all the way to the World Series.  On the year, Hampton went 15-10 with a 3.14 ERA.  The year before, he finished second in NL Cy Young voting when he went 22-4 with a 2.90 ERA when with the Houston Astros.

Given his free agency status following the 2000 season, it seemed pretty obvious that Hampton was about to make bank.  The Rockies ultimately gave him big money, signing him to an eight-year deal worth $123.8 million.  Unfortunately, both sides seemed to forget that the Rockies play in Coors Field, located in Denver, whose high elevation makes for tons of home runs.

As a result, Hampton lasted just two years with the Rockies, going 21-28 with a 5.75 ERA and horrific 1.67 WHIP.  However, it seemed that the Rockies dodged a bullet as following his being traded to the Florida Marlins and then the Atlanta Braves following the 2002 season, arm problems hampered the lefty.

He missed both the 2006 and 2007 seasons and considering how the contract he signed with Colorado was the highest in sports history at the time, there is no doubt in my mind that the Rockies regretted ever making that offer.

Detroit Tigers: The Hiring of Alan Trammell

I have long been of the opinion that just because a particular individual is a popular player on a certain team, it doesn't necessarily mean they are fit to be a manager or coach with said team.  The Detroit Tigers learned this the hard way when they hired ex-shortstop and former fan favorite Alan Trammell to be manager in 2003.  The team was coming off a 106 loss season, so team management thought bringing in someone who knew the franchise well would be a good fit.

Instead, it proved to be a disaster.  The Tigers lost 119 games in Trammell's first year at the helm and he lasted just three seasons in the Motor City.  His career managerial record stands at a less-than-average 186-300.

Houston Astros: Letting Carlos Beltran Walk

In 2004, the Houston Astros made headlines when they acquired talented outfielder Carlos Beltran from the Kansas City Royals on June 24.  At the time of the deal, Beltran was hitting .278 with 15 home runs and 51 RBI.  Once he was in Houston, it was as though he turned on the afterburners.

In 90 games with the team, Beltran hit just .258.  Yet, he also hit 23 home runs with 53 RBI and 28 steals.  He was instrumental in the Astros reaching the playoffs, where the St. Louis Cardinals beat them four games to three in the NLCS.  Beltran was a monster in the playoffs too, hitting .435 with eight home runs and 14 RBI.

He stated a desire to stay in Houston once his contract expired at season's end, but the team chose not to re-sign him.  Beltran ultimately signed a seven-year, $119 million deal with the New York Mets and was ultimately very effective despite being hampered by injuries the last few years of the deal.

Considering how Beltran was replaced with the largely one-sided Willy Taveras, the Astros really missed the boat on this one.

Kansas City Royals: Trading Johnny Damon

In 1995, Johnny Damon made his major league debut for the Kansas City Royals.  His speed, good bat and range in the field ultimately earned him a permanent spot in the lineup.  Over time, he established himself as one of the game's better leadoff men and showed great prowess at stealing bases and hitting for average while posting a high OBP as well.

Unfortunately, the Royals were in tight financial straits during Damon's tenure with the team and when his contract year drew close, the higher-ups thought it best to trade him and get prospects in return rather than lose him to free agency and be empty-handed when the dust settled.

Thus, in January 2001, Damon was traded to the Oakland Athletics in a three-team deal that also involved the Tampa Bay Devil Rays.  The Royals ended up receiving catcher A.J. Hinch from Oakland and relief pitcher Roberto Hernandez from Tampa Bay.  To be perfectly blunt, the Royals got short-changed.

Hinch lasted two seasons with the team and hit just .214 in 117 games.  Hernandez went 6-9 with a 4.21 ERA and 54 saves in two seasons, but he was already 36 years old at the time of the trade.

Damon, on the other hand, went on to be a very productive outfielder and won two World Series rings.  He is still active today.

Los Angeles Angels: Overpaying Gary Matthews, Jr.

In 2006, Gary Matthews, Jr. had an All-Star season with the Texas Rangers.  He hit .313 with 19 home runs and 79 RBI in 147 games and once he entered free agency, he became a player who received a big contract following one breakout year.  This contract came in the form of a five-year deal worth $50 million offered by the then-Anaheim Angels.

Yet, the deal was marred in controversy as shortly after it was signed, Matthews was reported to have used HGH at one point.  Still, the Angels kept the outfielder on board and the results were...well, uninspiring.

Matthews lasted just three seasons with the Angels, hitting .248 with 30 home runs and 168 RBI before requesting a trade and being sent to the New York Mets in 2010.  He appeared in 36 games for them before being released.

This contract just further proves that regular reserve players who have one big year after little time as a regular starter shouldn't receive big contracts with guaranteed money.

Los Angeles Dodgers: Hiring Grady Little

I'm still trying to wrap my head around this one.  The Los Angeles Dodgers needed a manager so before the 2006 season, they hired ex-Red Sox skipper Grady Little.

For those of you who are unaware, Little is the man responsible for one of the worst decisions in baseball history.  In Game 7 of the 2003 ALCS, with a rested bullpen at his disposal and his team leading the New York Yankees 5-2 in the bottom of the eighth inning, Little chose to let starter Pedro Martinez stay in the game despite being tired.

Sure enough, Martinez gave up a two-run double to Hideki Matsui and then a bloop single to Jorge Posada that tied the game.  The Yankees went on to win in extra innings and thus punch their ticket to the World Series.

Not that I'm complaining about the result, but what were the Dodgers thinking in hiring a manager who made such a bonehead move?  Would you have hired Little after that game?  I sure wouldn't have.

Little led the Dodgers to a playoff berth in 2006, but was generally mediocre in his two seasons there.  Combine that with the soap opera that was Frank and Jamie McCourt getting divorced, and the decision-makers for the Dodgers are definitely regretting this move.

Miami Marlins: Trading Miguel Cabrera

From 2003-2007, Miguel Cabrera was one of the top young players on the Florida Marlins.  Over that stretch, he showcased amazing power and hit .313 with 138 home runs and 523 RBI.  Unfortunately, he fell victim to team owner Jeffrey Loria's "no spending money until we get a new stadium" philosophy.

He was traded to the Detroit Tigers prior to the 2008 season and since then, he has been unbelievable.  Since the trade, he has hit .322 with 139 home runs and 461 RBI, winning the AL batting title in 2011.  Shortly after the trade, the Tigers signed him to an eight-year deal worth $153.3 million.

Now that the Marlins are actually making offers to the likes of Jose Reyes and Albert Pujols, this move won't prove to be so regretful if either signs with the team.  Still, what if the Marlins don't land Pujols to play first base?  They'll be left with a respectable, yet average option in Gaby Sanchez.

Only then will Loria realize that he should have paid Cabrera.

Milwaukee Brewers: Lowballing Paul Molitor

For 15 years, Paul Molitor was one of the most popular players on the Milwaukee Brewers.  He was the rare type of leadoff man who also had some power to go with a good contact bat and speed and when his contract expired after the 1992 season, it was no surprise that he wanted to stay with the team for whom he had played his entire career.

However, when negotiating time came along, team management did not treat their loyal star very well.  The 36-year-old Molitor was offered a one-year deal worth $2.5 million, $900,000 less than he made the previous year.  Here was someone who had hit .303 with 2,281 hits, 160 home runs, 790 RBI and 412 steals in 15 years with the team, and this was how they showed their desire to retain him?

Molitor rejected the deal and instead signed a three-year deal worth $13 million with the defending champion Toronto Blue Jays, with whom he won a ring in 1993.  Had the Brewers given the man his due respect, perhaps he could have been a Brewer for life.

Minnesota Twins: Extending Joe Mauer

Just before the 2010 season, the Minnesota Twins got a big monkey off their back and signed popular catcher Joe Mauer to an eight-year contract extension worth $184 million.  This money seemed warranted, seeing as how Mauer was coming off an MVP season in which he led the AL with a .365 batting average and also hit 28 home runs with 96 RBI.

Yet, the Twins started playing in their new stadium, Target Field, in 2010 and while Mauer hit .327, his power numbers dipped in the pitcher-friendly park.  In 2010, he hit just nine home runs while knocking in 75 RBI.

However, the Twins will ultimately come to regret this deal down the road because of Mauer's questionable durability.  At 6'5" and 235 pounds, there is no way he'll be playing catcher forever.  He's only 28 and has already spent time not only at catcher, but at first base and even the outfield.

His 2011 campaign exposed his durability issues as he appeared in just 82 games and hit a career-low .287 with just three home runs and 30 RBI.  Barring a major turnaround or a ballpark makeover, Twins management will regret giving out such a hefty extension now that the team no longer plays in the Metrodome.

New York Mets: Deferring Bobby Bonilla's Salary

Prior to the 1992 season, the New York Mets inked power-hitting third baseman/outfielder Bobby Bonilla to a five-year deal worth $29 million.  Considering how he had been part of the hot-hitting Pittsburgh Pirates teams of the late '80s-early '90s, this money seemed well deserved.

Yet, as the Mets suffered in the early 1990s, so did Bonilla's overall offense.  The home runs were there, but his average was not as he hit just .267 in three-and-a-half seasons with the team before being traded to the Baltimore Orioles. 

He then bounced around the majors before returning to the Mets as a reserve in 1999 and was a nonfactor.  He was placed on waivers and picked up by the Atlanta Braves, with the Mets agreeing to pay out the remainder of the contract by deferring the $5.9 million due.

This is when the regretful decision took place.  Under the terms of that agreement, the Mets will keep Bonilla on the payroll from 2011 to 2035, paying him $1.19 million every July 1 over that stretch at 8 percent interest.  Given the team's financial issues today, it's a safe bet that owner Fred Wilpon is banging his head against the wall over this decision.

New York Yankees: Carl Pavano's Contract

Carl Pavano went 18-8 with a 3.00 ERA and 1.17 WHIP pitching for the Florida Marlins in 2004, so of course the New York Yankees jumped on him once free agency began.  He signed a four-year, $39.95 million contract with the team and to date, Yankees fans still cringe at the mention of it.

Pavano's tenure with the team was largely ineffective as he went 4-6 with a 4.77 ERA in 2005 before going down with a shoulder injury.  He missed all of 2006 with a number of injuries and made two starts in 2007 before undergoing Tommy John surgery and returning for seven starts in 2008.

Overall, in his time with the Yankees, Pavano went 9-8 with a 5.00 ERA and 1.45 WHIP while making every penny from that contract.

Enough said.

Oakland Athletics: Trading Tim Hudson

The Oakland A's, since the start of the millenium, have employed a philosophy known as "Moneyball."  GM Billy Beane uses this approach to put together teams of players not based on their overall offensive production, but how often certain hitters get on base and the styles of various pitchers.

One of the better pitchers of the golden days of Moneyball was Tim Hudson, now of the Atlanta Braves.  Hudson debuted for the team in 1999 and was a key member of the Oakland pitching staff's "Big Three" of himself, Barry Zito and Mark Mulder.

In six seasons in Oakland, Hudson went 92-39 with a 3.30 ERA before being shipped to Atlanta prior to the 2005 season.  In return, the A's received outfielder Charles Thomas and pitchers Dan Meyer and Juan Cruz.  Here is where the regret comes in.

The point of Moneyball is to trade top players at their peak and thus bring in prospects who will help continue the cycle.  Unfortunately, such was not the case with the Hudson trade.

Thomas played in just 30 games for Oakland and hit .109 while Meyer had two awful stops with the team in 2007 and 2008, posting an 0-6 record and a 7.98 ERA.  Cruz spent one season with the team and went 0-3 with a 7.44 ERA in 28 games before being dealt to Arizona the following year.

Hudson, on the other hand, has become a valuable veteran presence in the Braves' young pitching rotation.  In Oakland, Moneyball is slowly dying.

Philadelphia Phillies: Overpaying Raul Ibanez

After a decent 2008 that saw him hit .293 with 23 home runs and 110 RBI for the Seattle Mariners, the Philadelphia Phillies chose to sign Raul Ibanez to a three-year deal worth $31.5 million.  Given the results of the deal, I'm thinking that team management didn't get the memo stating that Ibanez would turn 37 in 2009.

His first season in a Phillies uniform was a good one as he hit .272 with 34 home runs and 93 RBI, but his post All-Star Break numbers were far less impressive than his first half ones.  On top of that, age caught up with Ibanez as the power slowly diminished as did his range in the field.

Given how the team had players like John Mayberry and Domonic Brown available in the minors who could have manned left field, this was ultimately a waste of money.

Pittsburgh Pirates: Letting Jim Leyland Go

Jim Leyland managed the Pittsburgh Pirates for 11 seasons from 1986-1996 and while he had more mediocre seasons than good ones, he still turned the team into a contender thanks to his development of players like Bobby Bonilla and Barry Bonds.  Yet, once the stars left via free agency, the team was left depleted.

His 1995 Pirates squad only won 58 games, but rebounded to win 73 in 1996.  Leyland was not retained and went on to become the manager of the Florida Marlins, winning the World Series in his first season with the team.

That all being said, Leyland is a baseball guru who knows the game well.  Save for the Colorado Rockies, he has gotten the best out of every team he has managed and was well on the way to getting the Pirates back into contention.

Instead, team management chose to let him go and the Pirates have yet to have a winning season since 1992.

San Diego Padres: Trading Roberto Alomar and Joe Carter

In 1990, Joan Kroc sold the San Diego Padres to TV producer Tom Werner.  As occurs with most ownership changes, some of the more talented/potentially expensive players were traded.  In this case, prior to the 1991 season, the Padres traded second baseman Roberto Alomar and outfielder Joe Carter, both fairly popular players, to the Toronto Blue Jays for first baseman Fred McGriff and shortstop Tony Fernandez.

In terms of talent exchanged, this trade was fairly even.  However, neither player dealt to San Diego helped make the team any better.

McGriff had a solid two and a half seasons in San Diego, even leading the NL in home runs in 1992, but was dealt to the Atlanta Braves midway through 1993 as a cost-cutting measure.  Fernandez hit .274 in two seasons for the team before leaving for the New York Mets.  Thus, neither player was particularly instrumental in the team's World Series run in 1998.

On the other end of the trade, Alomar went on to have a Hall of Fame career as he and Carter won consecutive World Series titles in 1992 and 1993, Carter having the Series-winning home run in the latter Fall Classic.

And to think what could have happened in San Diego had the new owner chosen to build a team around Alomar and Carter.  Another dynasty could have been born.

San Francisco Giants: Signing Barry Zito

For the first seven years of his career, Barry Zito was an effective member of the young core of the Oakland A's pitching staff.  He became a household name following the 2002 season, when he won the AL Cy Young with a 23-5 record and 2.75 ERA.  He never had another dominant season for Oakland after that, but he was still a reliable arm down the stretch, many losses coming due to low run support.

Still, the San Francisco Giants rewarded Zito with a seven-year, $126 million contract plus an $18 million option for an eighth year.  Since moving across the Bay, Zito has not been the man the Giants thought they were getting.

Zito has gone 43-61 with a 4.55 ERA in his five seasons with the Giants, essentially becoming a non-factor the past two seasons.  He wasn't even on the team's World Series roster in 2010.

If that isn't a sign of regret by team management, then I don't know what is.

Seattle Mariners: Losing Lou Piniella

I remember when I first started watching baseball regularly, my dad and uncle would always get excited when the Seattle Mariners played the New York Yankees.  At first, I thought it was because we all had a collective man-crush on outfielder Ken Griffey, Jr.  Instead, the two men who got me into baseball were excited because of the team's manager, Lou Piniella, known to them as "Sweet Lou."

Simply put, Piniella was the man responsible for turning the Mariners into perennial contenders from the mid'90s to around 2002.  He took the team to the playoffs four times in 10 seasons, even winning a record-116 regular season games in 2001.

Still, rather than stay with the team and develop it further, Piniella resigned after the 2002 season after becoming frustrated with the team's front office.  He was of the opinion that the team's owners cared more about bottom-line results instead of acquiring quality players to help build a championship-caliber team, so he went to manage his hometown Tampa Bay Devil Rays.

Since Piniella's departure, the Mariners have struggled to contend and have yet to see the playoffs.  They used to have a lineup full of talent, and now it's basically Ichiro Suzuki and a bunch of ragtags.  Had Piniella been given reason to stay, perhaps the team finally would have gotten over that ALCS hump.

St. Louis Cardinals: None

After going through the history of the St. Louis Cardinals, I simply cannot find an offseason decision that has proved to be regrettable.  The only offseason regret that could come to pass would be if first baseman Albert Pujols departs for another team soon, as losing his leadership and powerful bat could prove to be catastrophic.

Tampa Bay Rays: Signing Manny Ramirez

In the long run, signing Manny Ramirez did not hurt the Rays at all.  Yet, the aftermath of it was just so embarrassing that if I were in Andrew Friedman's shoes, I'd be feeling pretty low about signing the man to a contract in the first place.

You see, the Rays signed Ramirez to a one-year deal worth $2 million despite the fact that he was on the decline and had already once been suspended for testing positive for steroids, not to mention his long history of attitude problems.  Still, he seemed like a good veteran presence and a decent power bat to have on a team full of young players.

However, Ramirez retired just five games into the 2011 season after going just 1 for 17.  Why was there such an abrupt retirement?  Well, Ramirez had apparently again tested positive for a banned substance and was facing a 100-game suspension.

Instead of coming forward and trying to save a little face in admitting his wrongdoing, he rode off into the sunset like a coward.  If the Rays' front office wasn't regretting signing him during the offseason, then perhaps they need to reassess how they view things.

Texas Rangers: The Alex Rodriguez Contract

Following a 2000 season that ended with a .318 average, 41 home runs and 132 RBI, Alex Rodriguez entered free agency looking for a ridiculously big contract.  The Seattle Mariners couldn't afford to keep him, so he hit the open market.  Rodriguez ultimately signed a then-record 10-year, $252 million deal with the Texas Rangers and was expected to do wonders for the franchise, eventually turning them into playoff contenders.

Yet, such a deal proved to be too expensive for the Rangers as it prevented them from bringing in talent to build around Rodriguez.  Sure, he had a phenomenal three years with the team and even won AL MVP in 2003, but the price was keeping the team from winning.

He was ultimately traded to the New York Yankees for Alfonso Soriano prior to the 2004 season, but there was a catch to the deal.  The Rangers had to pay $67 million of the $179 million remaining on the contract.  It was another six seasons before the team got back to the playoffs, even making the World Series in consecutive years.

Still, was such a wait worth the price?

Toronto Blue Jays: Trading Roger Clemens

Not that I'm complaining about the result of this trade, but I still have no clue as to why it even happened.  Prior to the 1999 season, the New York Yankees acquired ace pitcher Roger Clemens from the Toronto Blue Jays in exchange for infielder Homer Bush, relief pitcher Graeme Lloyd and fan-favorite pitcher David Wells.  This trade was a head-scratcher, considering how Clemens had gone 41-13 with a 2.33 ERA, 563 strikeouts and a 1.06 WHIP in his two seasons in Toronto, both of which had earned him AL Cy Young Awards.

Clemens went on to have a productive career with the Yankees, winning World Series rings in 1999 and 2000.  The rest of the players, on the other hand, became decent players on bad Toronto teams.

Bush was decent for Toronto in 1999, batting .320 with 32 steals, but was largely ineffective after that as he appeared in just 177 games over the next two and a half seasons before being released.

Lloyd appeared in 74 games for the Blue Jays in 1999 and posted a 3.63 ERA while Wells went 37-18 with a 4.47 ERA in a two-year stint.

In losing their top pitcher, then-Blue Jays GM Gord Ash set the team back years and it is still struggling to keep up in the extremely tough AL East today.

Washington Nationals: Signing Jayson Werth

Though the Washington Nationals have a history of losing dating back to their days as the Montreal Expos, none of the offseason moves from back then are regrettable as they were only made due to an extremely limited budget.  Now that the Nationals have money and will be contenders soon, it's safe to say that the signing of Jayson Werth is, as of now, the team's biggest offseason regret.

He was brought to DC on a seven-year, $126 million deal after hitting .282 with 63 home runs and 184 RBI for the Philadelphia Phillies from 2009-2010.  The World Series ring he won with the team in 2008 didn't hurt either.

Yet, Jayson Werth looked more like Jayson Werth-less his first year in Washington, hitting just .232 with 20 home runs and 58 RBI in 150 games.  It was a classic case of paying a decent outfielder a superstar's salary.

Barring a complete turnaround, Nationals GM Mike Rizzo is going to have a lot of headaches over this contract if Werth's lack of production keeps the team from contending.