5. Denny Neagle, P—5 years, $51 million from the Rockies in 2001
After going 15-9 with the Cincinnati Reds and New York Yankees in 2000, Denny Neagle signed a lucrative deal with the Colorado Rockies that made him one of the wealthiest pitchers in the game. Mr. Neagle quickly proved, however, that he was not worth the money.
Over the course of the next two seasons, Denny compiled a gaudy record of 17-19, with an ERA above five, gave up 55 home runs, and hit 17 batters. In an injury shortened 2003 season, he also went 2-4 with an ERA of 7.90.
Unfortunately for Denny, his troubles didn’t end there.
He missed all of the 2004 season with elbow ligament surgeries, and he was released by the Colorado Rockies after he found himself embroiled in legal trouble. After he was arrested with a hooker and driving under the influence, he was released by the team and sent on his way.
In 2005, he signed on with the Devil Rays, but once again was unable to play due to recurring injuries. After several other arrests and legal troubles, Neagle’s career ended in a sea of criminal activity and unrealized potential.
4. Barry Zito, P—7 years, $126 million from the Giants in 2007
If anyone personifies being overblown on the free agent market, it’s Mr. Zito. He came in to the Giants organization making a name for himself for the team across the Bay (the A’s), with his guitar playing antics and his ridiculous curve ball.
He threw at least 200 innings in each of his six full seasons with the Athletics, and he was a three-time All-Star. He also won the Cy Young Award in 2002 with a 23-5 record, and he struck out 205 batters in 2001. He also never missed a scheduled start. It was for all of these reasons that the Giants committed the biggest contract ever given to a pitcher to let him pitch in friendly AT&T Park.
The park and team have been anything but friendly to him.
In his two seasons in Rice-a-Roniville, Zito has a 21-30 record, with an ERA near 5.00 and 40 home runs given up. He also set a career high by allowing 102 walks in 2008.
Things got so bad for him last season that he was demoted from the starting rotation for part of the season, as youngsters Matt Cain and Tim Lincecum showed dominance and a reason for hope in San Fran.
3. Mo Vaughn, 1B—6 years, $80 million with Angels in 1999
Mo Vaughn came to the Angels after a checkered final season with the Boston Red Sox. He got into an altercation at a nightclub when he punched a man, and he crashed his truck on his way home from a strip-club. His off-field troubles didn’t affect his on-field track record, as he combined to slug 75 home runs with teammate Nomar Garciaparra.
When he came cross-country and suited up for the Halos, he was productive—when he was healthy. He hit 30-plus home runs in his first two seasons in Anaheim, but he caught a nasty case of the injury bug when he came to California.
In fact, before his first game, he fell down the dugout steps on his first play as an Angel and badly sprained his ankle. It was these kind of nagging injuries that led to him missing the entire 2001 season and he was subsequently traded to the Mets after the season.
When Troy Percival said that the Angels wouldn’t miss Vaughn’s leadership, Mo taunted his former team, saying that they had “no flags hanging at friggin’ Edison Field, so the hell with them”. It must have felt pretty good for Troy and the Angels to win the World Series the first season after Mo took his act to New York.
He played limited ball in 2002 and 2003, ballooned to 275 pounds, and was sidelined permanently by a knee injury that last season. The trade that netted the Mets Vaughn was orchestrated by Steve Phillips, who is casually referred to as “the GM” on ESPN. I wish my legacy was that I pulled off one of the worst trades in history and get a cushy job at ESPN.
2. Kevin Brown, P—7 years, $105 million in 1998 from the Dodgers
Quick! Tell me what you do with a 33 year old pitcher who had an 18-7 record for a team that made the World Series?
If you answered give him the first $100 million contract in Major League history, then you must be the GM of the Dodgers who decided to give exactly such a deal to Kevin Brown, who proceeded to win an average of nine games a season for the rest of his career.
After finishing third in Cy Young voting, Brown wanted to pay closer to his home in Georgia, but what kind of moron would turn down that kind of coin?
In his first season, he posted an 18-9 record with an even 3.00 ERA, which is obviously respectable. After this, however, his performance began to slowly suffer as he caught the injury bug, missing significant time between 2000 and 2002. In 2003, he had a resurgence of sorts, going 14-9.
This number, however, is undermined, as Brown was one of the players suspected of steroid abuse in the Mitchell Report. Kirk Radomski claims he sold Brown HGH between 2000 and 2001.
In 2003, he was traded to the New York Yankees, and his most notable accomplishment in the Bronx was breaking his hand after arguing with Joe Torre. He tried one more comeback attempt in 2005, going 4-7 with an ERA of 6.50.
1. Mike Hampton, P—8 years, $121 million in 2001 from Rockies
If Denny Neagle and Mike Hampton have taught Major League pitchers anything, it is this: when Colorado comes calling with huge contracts, RUN AWAY! Coors Field is apparently where good pitchers go to die, and Hampton was not an exception to this rule.
In his first season in Colorado, he went 14-13 with an ERA of 5.12, and in his next season, he was even worse, going 7-15 with an ERA of 6.15.
After these two horrendous years, he was traded to the Florida Marlins, and then to the Atlanta Braves.
In 2003, he won 14 games, and in 2004, he won 10 of his final 11 starts, but in 2005, the wheels came off again. He managed 12 starts before being lost for the season, and then had Tommy John surgery, costing him his entire 2006 season.
In 2007, he was expected to rejoin the rotation, but after an oblique injury, it was again revealed he had recurring elbow pain, and had another reconstructive procedure, costing him the entire season.
In 2008, he actually managed to make a couple of starts, going 3-4 with a 4.85 ERA, giving up 10 home runs in 13 starts, and walked 28 batters in 78 innings.
He currently has a contract with the Houston Astros, and is still wanting to try to make a name for himself as a quality middle of the rotation pitcher.
Well, there you have it: my list of the 10 worst baseball free agent signings ever! Will Francisco Rodriguez or CC Sabathia make their way on here? We will have to wait and see.





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