Friday 5’s: Top 5 worst free agent contract signings of the past 10 years.

          Manny Machado and Bryce Harper will be making some serious cash this offseason. Both players are expected to sign contracts worth more than 200 Million dollars. While these players have proven throughout their careers that they are worth the money now, we have seen players sign long contracts and have it not workout for the team that signed them. These are what I think are the 5 worst free agent contract signings of the past 15 years.

  1. Albert Pujols, LAA  (signed a 10 year, $240 million dollar contract in 2012)

          From 2001-2011, you could argue that Albert Pujols was the best hitter in baseball. In those years, Pujols had made 9 all-star teams, won 6 silver slugger awards, 3 MVP awards, and had 2 World Series rings under his belt. Throughout those 11 years, Pujols had averaged 41 home runs, 121 runs batted in (RBI’s), and a .329 batting average. He was on track to be the greatest statistical hitter of all time and was even on pace to become the all time home run king. After winning the World Series with the Cardinals in 2011, Pujols hit the free agent market for the first time in his career going into his age 32 season, and signed a record 10 year 240 million dollar contract with the Los Angeles Angels.

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Image: Pujols hitting home run at Busch Stadium

          Since signing with the Angels, Pujols production has dropped considerably, averaging just 27 home runs, 93 RBI’s, a .259 average, with only 1 all star appearance. These numbers aren’t terrible but when you look at his previous years, and the amount of money he is making, the Angels were paying for the player from 2001-2011. Pujols is signed through 2022, Pujols’ age 42 season, so it seems the Angels are stuck with him until then, unless some team wants to take on him and his over priced contract.

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Image: Pujols flips his bat after a strikeout at Angel Stadium
  1. Zack Greinke, ARZ (signed a 6 year, $206.5 million dollar contract in 2016)

          Zack Greinke became a household name in 2009, when he won the Cy Young award with the Kansas City Royals. Greinke went 16-8 with a league leading 2.16 earned run average (ERA) and 242 strikeouts in 229 1/3 innings pitched. Greinke bounced around a few teams until landing with the Dodgers in 2013. From 2013-2015 Greinke became one of the top pitchers in baseball going 51-15 with a 2.33 ERA with 555 strikeouts in 602 ⅔ innings pitched. In 2015, the year before he signed this deal, Greinke lead all of baseball in winning percentage (.864), ERA (1.66), and Walks and hits per innings pitched or WHIP (0.844). He finished 2nd in the Cy Young voting, however he was unhappy being seen as the #2 started on his team behind Clayton Kershaw.

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Image: Zack Greinke is introduced as a Los Angeles Dodger

          While the Dodgers offered him more money in total, he accepted a 6 year 206.5 million dollar deal with the Arizona Diamondbacks. While Greinke has 2 all-star appearances, and 3 gold glove awards, the Diamondbacks have won 1 playoff game in Greinke’s 3 seasons, and due to his massive contract, the team could not re-sign their homegrown star Paul Goldschmidt, who was traded to St.Louis a few months ago. Arizona will now start to rebuild for the future, and will look to try and trade the 34 year-old Greinke in order to clear cap space.

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Image: Greinke upset during mound meeting in Arizona
  1. Pablo Sandoval, BOS (signed a 5 year $95 million dollar contract in 2015)

          Pablo Sandoval broke out in 2009 with the Giants after hitting .330 with 25 home runs and 90 RBI’s, for the SF Giants. From then until 2014, Sandoval collected 2 all star appearances, 3 World Series rings, and was the 2012 World Series MVP when the Giants swept the Tigers 4-0 in the fall classic. Sandoval averaged 17 home runs, 69 RBI’s, and hit .292, and the Red Sox who were desperate to fill a hole a 3rd base, signed the 3 time world champion to a 5 year 95 million dollar contract. In his 1st season with the Red Sox, Sandoval’s production took a turn for the worst as he hit .245 with just 10 home runs and 47 RBI’s in 125 games for the Red Sox.

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Image: Sandoval celebrates his 2012 World Series MVP trophy

          The 3rd baseman managed just 3 games and 7 plate appearances for the Red Sox in 2016 because he refused to get into better shape. Sandoval showed up to spring training that year nearly 40 pounds overweight and it didn’t seem like he was going to be going on a diet anytime soon while playing for the Red Sox. The Red Sox released him in 2017 and he was picked up by his old team to be a backup 3rd baseman. However due to his original contract with the Red Sox, they will have to pay Sandoval $18 million dollars a year to play for another team, until 2020 when the Red Sox can buy him out of his contract for $5 million dollars.

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Image: Sandoval strikes-out at Camden Yards vs Orioles
  1. Melvin (B.J.) Upton Jr., ATL (signed a 5 year $72.25 million dollar contract in 2012)

          In his early years with the Tampa Bay Devil Rays/Tampa Bay Rays, Melvin (B.J.) Upton was considered a 5-tool outfielder that could be the centerpiece of a contending team. From 2007-2011, Upton averaged 19 home runs, 71 RBI’s, 36 stolen bases, and a .257 batting average. Upton was also a way above average center fielder and was on track to becoming one of the best outfielders in all of baseball. In 2011, Upton had 28 home runs, 78 RBI’s and 31 stolen bases, making him a threat at the plate and on the base paths. When the Braves signed him in 2012, they thought they had found the 1 missing piece keeping them from making a deep run into the postseason.

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Image: Melvin (B.J) Upton hits walk-off home run for Rays at Tropicana Field

          Instead, Upton averaged 11 home runs, 31 RBI’s 16 stolen bases, and hit just .196 in 2 seasons with the Braves. Atlanta traded the outfielder to San Diego following the 2014 season, and Upton was out of baseball by the end of the 2016 season. In an interview with Fox Sports in 2015, Upton admitted he had felt pressure to live up to the hype from his massive contract, and felt that it was a distraction to him and his on field career. The Braves just finished paying off Upton in 2017, and have found a new core of outfielders to build around, but to go from being considered one of the most versatile outfielders in all of baseball to being out of baseball in just 5 years is quite the turn around, and was quite the waste of money for the Braves.

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Image: Melvin (B.J) Upton walks back to dugout after recording an out at Turner Field
  1. Josh Hamilton, LAA (signed a 5 year $125 million dollar contract in 2013)

          This is by far the worst free agent signing ever, and ofcourse it comes from the team who has made 3 of the worst contracts in the 21st century, (CJ Wilson 2012, 5 year $77 million). Hamilton didn’t make it to the MLB until his age 26 season, after he battled drug and alcohol addiction for most of his early career. However in 2007, Hamilton had a breakout season for the Texas Rangers hitting .304 with 32 home runs and a league high 130 RBI’s. Over the next 5 years, Hamilton would make 5 all star teams, win the 2010 MVP, and help lead the Rangers to the World Series in 2011 and 2012. During those seasons, Hamilton averaged 29 home runs, 101 RBI’s, and hit .303. The Angels, who were looking to add to their line up of Albert Pujols and Mike Trout, decided to bring the former MVP Hamilton over to give them a “3 headed monster” in the middle of their line up in Trout, Pujols, and Hamilton. Hamilton played well in his first season in Los Angeles, however his numbers took a dip as Hamilton managed just 21 home runs, 79 RBI’s, and hit a career worst .250 in 151 games for the Angels.

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Image: Hamilton slugs a home run for the Rangers at Globe Life Park

          This was just the beginning. Hamilton played just 139 games over the next 2 seasons, as he had 18 home runs, 69 RBI’s and hit .258, while suffering a drug relapse that caused him to miss most of the 2015 season. In 2016 the Angels wanted to get rid of Hamilton and sent him to his former team, the Texas Rangers. However, as part of the deal, the Angels had to pay Hamilton still, as he had 2 years left on his original deal. The Angels paid Hamilton $26 million dollars in 2016 to play for the Texas Rangers, more than they were paying league MVP Mike Trout that year. Hamilton retired from baseball in 2016, meaning the Angels only got about 1 ½ years of production from Hamilton’s original 5 year deal.

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Image: Hamilton strikes-out and flips bat at Globe Life Park


Honorable Mentions: Carl Crawford, Dan Uggla, Robinson Cano

Do you agree with my picks? Who’s contract do you think was the worst? Let me know in the comment section below, and as always, thanks for reading!

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