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MLB Free Agency: The 10 Most Shocking MLB Free-Agent Moves of the Past 15 Years

Chris SchadContributor IIIDecember 20, 2016

MLB Free Agency: The 10 Most Shocking MLB Free-Agent Moves of the Past 15 Years

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    The argument could be made that Major League Baseball's hot stove season may be better than the regular-season games that are played in the middle of June.

    What makes MLB's offseason great is that it can get unpredictable, imaginative and even shocking as each big-name free agent is taken off the board and placed into a new uniform for the following spring.

    As we get into this offseason's array of mystery teams, interesting signings and big-money contracts to undeserving players, here's a look at some of the most shocking moves in MLB free agency over the past 15 years.

10. Mo Money, Mo Problems for the Angels

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    Mo Vaughn hit a walk-off grand slam to begin the 1998 season for the Boston Red Sox, but The Hit Dog's career went downhill from that moment on.

    After a season-long spitting contest between himself and Red Sox management over a new contract, Vaughn packed his bags and signed a six-year, $80 million contract with the (then) Anaheim Angels.

    Unlike his final Opening Day with the Red Sox that ended with late-inning heroics, Vaughn fell down the visiting dugout steps on the first play of his career with the Angels and battled injuries ever since.

    The Angels finally got rid of Vaughn in a trade to the New York Mets prior to the 2002 season which triggered a rant from Vaughn...

    Ain't none of them done a damn thing in this game, bottom line. They ain't got no flags hanging at ... Edison Field, so the hell with them.

    The Angels would go on to win the 2002 World Series. 

9. Randy Johnson Signs with the Diamondbacks in Their 2nd Year of Existence

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    Randy Johnson was one of the most dominating pitchers in the history of Major League Baseball. With that being the case it was assumed that a team with some prestige would be a front-runner when he hit the open market after the 1998 season.

    Instead, The Big Unit signed with the Arizona Diamondbacks. The Diamondbacks were entering their second year of existence and were looking to compete sooner rather than later by signing Johnson.

    The Diamondbacks didn't stop there, as they went and traded for Curt Schilling in the summer of 2000 to set up the 1-2 punch that won the franchise's first World Series in 2001.

    Johnson has now had his No. 51 retired by the Diamondbacks, as he is one of the greatest players in the franchise's short history.

8. Giants Pay Barry Zito Four Years Too Late

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    Barry Zito was unhittable upon making his major league debut with the Oakland Athletics in 2000. Being paired with Mark Mulder and Tim Hudson, the Athletics made a run of success under Billy Beane's Moneyball philosophy.

    Of course, players like Zito do not seem to stick around Oakland for long. Fortunately for Zito, he didn't have to go far as he jumped over the bay and signed with the San Francisco Giants.

    The Giants were more than willing to welcome Zito to their rotation and gave him a seven-year, $126 million contract in January of 2007. Problem is, Zito was starting to fall off a cliff.

    While Zito did win the 2002 Cy Young Award with a record of 23-5 and 2.75 earned run average, he had been a .500 pitcher with an ERA flirting with four since then. The Athletics figured he wasn't worth a new contract, but the Giants ignored it, seeing it as an opportunity to add an ace.

    The contract has failed miserably with Zito compiling a 58-67 record and 4.48 ERA in six seasons with the Giants.

    While Zito seems to have resurrected his career with a 15-8 (4.15 ERA) record in 2012, the Giants are still kicking themselves for paying Zito four seasons too late.

7. Gary Matthews Jr. Becomes Shockingly Overpaid

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    In the first seven seasons of Gary Matthews Jr.'s career, he hit .249 with 59 home runs and 236 runs batted in while making stops in six different cities. Basically, Matthews was giving the production of a fourth outfielder.

    Then 2006 happened. Matthews had a career year for the Texas Rangers, hitting .313 with 19 home runs and 79 runs batted in, while making his first All-Star appearance and making one of the greatest defensive plays ever by robbing Mike Lamb of a home run in 2006.

    With a scorecard of seven mediocre seasons and one decent season, the most logical decision the Los Angeles Angels of Anaheim could think of was to sign him to a five-year, $50 million contract to become their center fielder.

    Roughly two months later, Matthews was busted for allegedly using Human Growth Hormone prior to it being added to MLB's banned substance list. Matthews was grandfathered into the old list of banned substances, which resulted in no punishment. (In a related note, Matthews has denied taking HGH.)

    However, his performance severely declined, and he was eventually replaced by another high-priced free agent acquisition in Torii Hunter prior to the 2008 season.

6. Johnny Damon Becomes a Yankee

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    Upon going to a Twins game in 2005, I overheard a fan attempting to engage in a conversation with Johnny Damon. It went something like this...

    FAN: Johnny! How does it feel knowing that the entire city of Boston wants to kill you?

    DAMON (turning around, looking nervous and making the cross): I pray every day...

    It's an interesting voyage from being a cult hero in Boston to becoming a bona fide villain as a member of the New York Yankees, but this one was personal considering Damon's place in the Red Sox's history.

    Damon was one of the famed "idiots" who helped end Boston's 86-year World Series drought in 2004. With his trademark beard and laid-back personality, he became a fan favorite as he entered his final season with the Red Sox in 2005.

    As the Red Sox refused to give Damon more than a three-year contract, the famed outfielder decided to hit Boston where it hurts by signing a four-year, $52 million contract with the Yankees, despite professing his love for Boston seven months earlier...

    There's no way I can go play for the Yankees, but I know they're going to come after me hard. It's definitely not the most important thing to go out there for the top dollar, which the Yankees are going to offer me. It's not what I need.

    Without his beard and long haircut, Damon hit .285 in four seasons with the Yankees, including earning his second World Series ring in 2009.

5. Red Sox Pay $51 Million to Talk to Dice-K

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    Upon dazzling scouts at the inaugural World Baseball Classic, Daisuke Matsuzaka was going to bring a bidding war nobody had seen before when he was posted by his Japanese parent club, the Seibu Lions. Leave it to the Boston Red Sox to live up to the hype.

    What was an intense posting process ended with the Red Sox beating the New York Yankees, New York Mets and Texas Rangers with a bid of $51.1 million to talk to the Japanese phenom.

    You read that right: $51.1 million not to sign a pitcher, but to talk to a pitcher about possibly signing a contract.

    The $51.1 million figure was roughly three times the payroll of the Lions in 2006, and after a six-year, $52 million contract was agreed upon by the Red Sox and agent Scott Boras, the owners of the parent club had to have been doing backflips.

    The Red Sox? Not so much.

    Matsuzaka was solid in his first couple seasons in the major leagues (including 18-3 with a 2.90 earned run average in 2008), but he wound up with pitch count and control (4.3 walks per nine innings in his career) issues that got worse as his career progressed.

    After undergoing Tommy John surgery in 2011, Matsuzaka returned to make 11 starts for the Red Sox in 2012, going 1-7 with an 8.28 ERA.

    All this after spending $51.1 million to talk to a pitcher.

4. Cliff Lee Returns to Philadelphia After Being Traded to Seattle

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    In the winter of 2009, the Philadelphia Phillies traded Cliff Lee to the Seattle Mariners in order to restock its farm system after acquiring Roy Halladay from the Toronto Blue Jays. With Lee becoming a free agent the season after, many thought that Lee's days in a Phillies uniform were numbered.

    The Mariners would flop in 2010, and Lee would be traded to the surging Texas Rangers. After leading them to the franchise's first World Series appearance, a bidding war between the Rangers and the New York Yankees ensued.

    As Lee went to his home state of Arkansas to mull the two options over, he came to the realization that Philadelphia felt like home and urged his agent to get a deal done for his return.

    After turning down a seven-year, $148 million offer from the Yankees, Lee signed a five-year, $120 million contract with the Phillies and formed one of the most-feared rotations in baseball history with Halladay, Cole Hamels and the also recently acquired Roy Oswalt.

    The "Four Aces" breezed to the National League East championship in 2011 but were eliminated by the St. Louis Cardinals in the National League Division Series.

    The second year for Lee didn't go as well, as the Phillies' potent offense suddenly got old and ineffective, handing Lee one of the worst seasons in his career in terms of win-loss (6-9), but he was effective thanks to a 3.16 earned run average.

    With three years to go, the Phillies should get their money's worth from Cliff Lee. 

3. Prince Follows in His Father's Footsteps

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    The relationship between Prince Fielder and his father, Cecil, has been a rocky one over the years. However, the same can not be said of Fielder's relationship with the Detroit Tigers.

    As Cecil was becoming one of the first major leaguers to hit 50 home runs in a single season, Prince was getting stuffed into garbage cans and hitting majestic bombs out of Tiger Stadium as a young boy.

    The way that Prince was treated was not forgotten, and Fielder showed his gratitude by accepting a nine-year, $214 million offer.

    The story of Prince's Detroit upbringing makes signing with the Tigers seem logical, but the Tigers had players who made the signing seem like a case of an owner playing fantasy baseball with real money.

    The Tigers already had Miguel Cabrera, who took all of 14 games upon his 2008 arrival to prove that he might be better suited for first base defensively, and Victor Martinez was on the Tigers' roster as their designated hitter. In other words, it seemed like Prince's positions had already been filled.

    Then, Victor Martinez tore his ACL while working out during the winter of 2011. It seemed like the Tigers would try to fill from within and then...boom! Prince was a Tiger.

    To further accommodate Fielder, Cabrera agreed to move back to third base. The move raised eyebrows around the country as the Tigers at times looked like a drunken softball team in the field.

    Through Cabrera's transition period, the Tigers won the American League pennant while their new third baseman became baseball's first Triple Crown winner since 1979.

2. Albert Pujols Ditches the St. Louis Cardinals

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    Prior to free agency, baseball players and their employers often had the same relationship as a strong marriage. While players and owners would fight and bicker about contracts and the personnel around them, if the player was treated well by the franchise, he would always be known as a member of that team.

    With the evolution of free agency, the loyal player-owner relationship has gone into the same ditch as the long-lasting marriage these days.

    When Albert Pujols retires, odds are that baseball fans will remember him as a St. Louis Cardinal. Over 11 seasons with the Cardinals, Pujols led the Redbirds to two World Series Championships (2006, 2011) and won three National League Most Valuable Player awards (2005, 2008, 2009).

    As Pujols entered the final year of his contract, talks would break down in spring training. However, nobody expected that Pujols would actually leave.

    As both sides remained quiet through the season at Pujols' request, everybody still expected that something would get done for the star slugger to remain in St. Louis.

    As time ran short on negotiations, Pujols still wanted to be compensated like his fellow superstars had been in the past decade, but the Cardinals were unwilling to give him a long-term contract at age 32.

    With that, the Los Angeles Angels swooped in and signed Pujols to a 10-year, $240 million contract to the shock of millions. Despite a likely regression in Pujols' production, the Angels knew that if they gave him what he wanted, "The Machine" would likely be theirs.

    One year into the contract, the Angels might feel like they haven't gotten what they paid for with Pujols having an "off year" of .285 with 30 home runs and 105 runs batted in.

    In a worst-case scenario, Pujols' supposed regression could continue as he gets older, making this contract another colossal bust for owner Arte Moreno.

1. Alex Rodriguez Introduces MLB to the "Mega Deal" in 2000

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    As millions of Americans engage in their annual holiday shopping, they will unknowingly participate in another American tradition in about a month that involves a blood-curdling scream upon receiving their January credit card bill.

    This tradition is known as sticker shock. Coincidentally, the Texas Rangers know all about this phenomenon after signing Alex Rodriguez to a record-breaking 10-year, $252 million contract in the winter of 2000.

    A-Rod entered that winter as perhaps the most coveted free agent in the history of Major League Baseball.

    With career totals that were poised to clinch his spot in Cooperstown by the time he hit age 30, everybody knew that not only could the Seattle Mariners not afford to keep him but also that Rodriguez would get paid in the process.

    With that in mind, former Rangers owner Tom Hicks made the decision to give Rodriguez a contract that perhaps only the New York Yankees could afford at the time.

    In the short term, things worked well as Rodriguez put up monster numbers in his first two seasons in Texas, including winning the 2003 American League Most Valuable Player award despite being on a last-place team.

    As time wore on, Rodriguez's contract crippled the Rangers and eventually forced them to file for bankruptcy before A-Rod's presence could produce a single championship. He was traded to the Yankees in a cold twist of irony prior to the 2005 season.

    The Rangers weren't the only ones to feel the ramifications of the first "mega deal," as several players have demanded incredibly high salaries since then.

    Albert Pujols and Prince Fielder are two of the most recent players to cash in on this trend, and there will be many more to follow.

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