MLB Free Agency: The 10 Most Shocking, Baffling Signings in MLB History
Throughout MLB history there have been countless examples of irresponsible overspending. With no salary cap, general managers are able to throw money around like they’re playing Monopoly, only I’m not that careless while playing a game.
This is the sport that saw Alex Rodriguez sign two contracts valued at over a quarter billion dollars. A sport where eight teams have nine-figure payrolls. A sport where one player can out-earn an entire team.
So in the history of this lucrative sport, what are the most baffling signings? Which undeserving players have benefited the greatest?
With free agency ongoing, we could be adding to this list shortly, but for now, I present the 10 most shocking signings in MLB history.
Honorable Mention
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Miguel Batista (three years, $25 million)
Carlos Beltran (seven years, $119 million)
Adrian Beltre (five years, $64 million)
Milton Bradley (three years, $30 million)
Kevin Brown (seven years, $105 million)
AJ Burnett (five years, $82.5 million)
Kevin Millwood (five years, $60 million)
Carl Pavano (four years, $40 million)
Carlos Silva (four years, $48 million)
Jason Schmidt (three years, $47 million)
Vernon Wells (seven years, $126 million)
10. Alfonso Soriano (Eight Years, $136 Million)
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There was a time that Alfonso Soriano was worth nearly $20 million per season. Too bad for the Cubs that time has come and gone.
After posting a career season with the Washington Nationals in 2006 (.277 with 46 HR and 41 SB), Soriano inked a massive eight-year contract worth $136 million. Thus far the results have been hugely disappointing.
In four seasons Soriano has batted .271 while averaging 26 HR and 13 SB. Respectable numbers, but not deserving of one of the game’s most lucrative contracts. The worst part? Soriano looks to be on the decline and at age 34, still has four years remaining on his contract.
In fact, before this contract has run its course, he could end up skyrocketing up this list. It’s an untradeable contact that the Cubs may eventually need to eat a large portion of. That will leave a sour taste in your mouth.
9. Albert Belle (Five Years, $65 Million)
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Growing up Albert Belle was one of my favorite players. His Indian teams were loaded with talent and his juiced up body was a home run hitting machine.
Between 1991 and 1998, Belle crushed 294 bombs and was recognized as one of the best power hitters in baseball. Then in 1999, a 32-year-old Belle signed a lucrative five-year contract with the Orioles valued at $65 million (at the time making him the highest paid player). The results were less than inspiring.
Belle hit 60 dingers in his first two seasons with Baltimore before a degenerative hip condition forced him to retire with three seasons left on his contract. While you would think that meant he lost out on his paycheck, you would be wrong. Belle collected $39 million as a member of the 40-man roster while the Orioles were reimbursed by their insurance policy.
8. Kei Igawa (Five Years, $46 Million)
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During the winter of Dice-K, Kei Igawa was the appetizer. The Japanese lefty signed a five-year, $20 million contract after the Yankees surrendered a $26 million posting fee for the rights to negotiate.
How did Igawa reward the Yankees carefree spending? By pitching only 71 innings in 16 games with a 2-4 record and 6.66 ERA over two seasons.
That means New York spent about $648,000 per inning! $2.875 million per game! $23 million per win! I’ve heard of wiping with hundreds, but I’ve never heard of a money flush quite like this.
7. Darren Dreifort (Five Years, $55 Million)
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Despite the fact that Dreifort has a career losing record of 39-45 and a history of arm troubles, Scott Boras bent over the Dodgers brass and landed Dreifort a five-year contract worth $55 million.
Over the duration of that contract, Dreifort played only three seasons, making a paltry 26 starts. For those of you doing the math at home, that’s over $2 million per start.
Dreifort was 4-7 with a 5.13 ERA in 2001 before missing the entire 2002 season due to injury. Dreifort went 4-4 in 10 starts in 2003 before returning as the league’s highest-paid reliever in 2004.
Contracts like this are why I loathe Scott Boras and why many of us believe we could be major league GM’s.
6. Gary Matthews Jr. (Five Years, $50 Million)
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In 2006 as a member of the Rangers, Gary Matthews Jr. easily recorded the best season of his career. Typically a low-average hitter, GMJ batted .313 with 19 jacks and 79 ribbies.
Looking to improve an outfield that already included Garret Anderson and Vladimir Guerrero, the Angels panicked and overpaid, doling out $10 million a year to a one-hit wonder.
In three seasons in Anaheim, Matthews batted .248 with 30 homers and 271 strikeouts. Matthews was eventually traded to the Mets, but Anaheim was forced to pay for all but $2 million of his bloated contract.
5. Denny Neagle (Five Years, $51.5 Million)
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In the winter of 2001, the Rockies were dedicated to improving their pitching staff. Their offense had thrived due to the thin mile high air, and it was time to complement their O with some D. Logically they went to Denny Neagle, who had recorded a 4.52 ERA the previous season.
Neagle pitched only 370 innings over the duration of his contract while posting a hideous 5.57 ERA. It was the biggest bust I had seen since watching Peter North. Neagle went on to have ligament and elbow surgery, and was ticketed for soliciting oral sex.
Due to a morality clause, the Rockies were able to void his contact, but it remains one of the most atrocious deals of all time.
4. Mo Vaughn (Six Years, $80 Million)
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From 1991 to 1998, Mo Vaughn was Boston royalty. Anchoring the Red Sox lineup, Vaughn batted .304 with 230 home runs and 752 RBI in eight season, including his MVP-winning 1995 campaign (.300, 39, 126).
After batting .337 in 1998, the big bopper wanted more dinero and opted for free agency. Leaving the friendly confines of Fenway Park, Vaughn accepted a six-year deal with the Angels for $80 million.
Vaughn struggled his first two seasons, watching his batting average plummet while his power waned. In 2001, Vaughn fell down the visitor’s dugout steps and missed the entire season. In the offseason he was dealt to the Mets for Kevin Appier before playing one more full season and riding into the sunset.
Mo played only 27 games after the 2002 season, yet still made well over $20 million in that time. Not exactly a great investment.
3. Chan Ho Park (Five Years, $65 Million)
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After posting a 3.50 ERA and 218 strikeouts in 234 innings as a member of the Dodgers, Chan Ho Park was sitting pretty. Sure his numbers were devalued a bit playing in the Dodgers' spacious stadium, but he was in line for a good contract. He was given a great one.
The Rangers, desperate to shore up their pitching woes, signed Park to a five-year, $65 million dollar contract. Despite a 3.77 career ERA with the Dodgers, Park imploded in Texas.
In three-and-a-half seasons before being dealt to the Padres, Park went 22-23 with a woeful 5.79 ERA.
2. Barry Zito (Seven Years, $126 Million with $17 Million Player Option)
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Every time I see Zito’s contract, I cringe. I can’t help it. The former Cy Young Award winner was billed by agent Scott Boras as the modern age Sandy Koufax, and the Giants bought the act hook, line and sinker.
Zito is entering the fifth year of his contract and things in San Francisco have gotten ugly. The southpaw has posted a 4.45 ERA while a member of the Giants versus a 3.55 ERA in his seven years with the A’s. Zito lost a lead-leading 17 games in 2008 and was held out of the postseason rotation while his teammates carried the team to its first World Series win since 1954.
The Giants' biggest mistake in signing Zito? Ignoring a trend of rising walks and waning strikeouts.
1. Mike Hampton (Eight Years, $121 Million)
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Back in 2001, Mike Hampton was considered far and away the best free agent pitcher on the market. Just one season after going 22-4 with a 2.90 ERA and leading Houston into the playoffs, Hampton posted a 3.14 ERA as his Mets made it all the way to the World Series.
The Rockies, desperate for pitching help, decided to make Hampton the highest paid pitcher of all time by doling out an eight-year, $121 million dollar contract.
At the time this signing was ridiculed, and the deal only got worse with age. Hampton lasted only two seasons in Colorado where he posted a 5.75 ERA before being dealt to the Braves.
While some may try to blame his struggles on the thin air at Coors Field, the truth is Hampton was never an elite pitcher. Wildly erratic, Hampton combined for 200 walks in two seasons before signing with Colorado and still recorded a 5.10 ERA on the road.
