The 20 Worst Free Agent Signings of the Last 15 Years

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Here are the 20 worst free agent signings of the last 15 years. All are listed in chronological order. I’ve also included their stats over the period of the contract, no matter what team they were on.

December 1, 1998 – Albert Belle, 5 yrs $65MM by the Baltimore Orioles
What it got: 1169 AB, 60 HR, .289/.371/.509
“Joey” Belle was one of the big hitters at this time. He cashed in on his second big free agent deal when the White Sox let him out of his contract; he had a clause that said he could re-negotiate his current contract if he fell out of the top 3 paid players. The White Sox refused to re-negoitate and he signed a huge deal with Baltimore. After 2 seasons, Belle was forced to stop playing due to a degenerative hip condition.

December 11, 1998 – Mo Vaughn, 6 yrs $80MM by the Anaheim Angels
What it got: 1704 AB, 98 HR, .267/.346/.481
Vaughn was probably one of the top hitters in the game when he began having problems with management in Boston. This resulted in him leaving for the Angels and the largest baseball contract at that time. After 2 injury filled seasons with the Angels (and missing another season), he was shipped to the Mets, where he would retire after battling more injuries.

December 12, 1998 – Kevin Brown, 7 yrs $105MM by the Los Angeles Dodgers
What it got: 72-45, 3.23 ERA, 1078 IP, 7.66 K/9, 3.31 K/BB
Brown was a full season removed from helping the Marlins win their first World Championship and weeks removed from winning 18 games for the Padres. The results got him a large contract with the Dodgers; he became the first $100MM player in the game. While he started off pretty well, injuries set in. He only pitched 200 innings in 1 of the final 5 seasons. He was shipped off to the Yankees; they traded their headache (Jeff Weaver) for the Dodger’s one. He retired at the end of the contract.

December 13, 1999 – Greg Vaughn, 4 yrs $33MM by the Tampa Bay Devil Rays
What it got: 1234 AB, 63 HR, .225/.333/.436
Vaughn was signed for one reason – to hit for power. Coming off a 45 homer season, Vaughn’s age started to show; his power numbers dropped each year. It got so bad that the Devil Rays ended up releasing him at the begining of the 4th year.

December 4, 2000 – Denny Neagle, 5 yr $51MM by the Colorado Rockies
What it got: 19-23, 5.57 ERA, 370.1 IP, 6.59 K/9, 2.01 K/BB
This was a bad year for pitchers contracts. Neagle was coming off a decent season with the Braves when he hit the jackpot. He followed it up as most free agent pitcher do when they hit Colorado – he bombed. Luckily for the Rockies, he got caught soliciting a prostitute and they were able to void the last year and option of his deal.

December 11, 2000 – Kevin Appier, 5 yrs $42MM by the New York Mets
What it got: 33-32, 4.18 ERA, 510.1 IP, 6.36 K/9, 2.07 K/BB
Appier was coming to the end of his career when the Mets threw a lot of money at him. What made this even worse is they traded him to the Angels for the even worse contract of Mo Vaughn.

December 11, 2000 – Darren Dreifort, 5 yrs $55MM by the Los Angeles Dodgers
What it got: 9-15, 4.64 ERA, 205.2 IP, 9.67 K/9, 2.05 K/BB
This is just another sign that Scott Boras is the devil. Dreifort had solid number; some how Boras convinced the Dodgers he was an ace and would receive a large deal on the open market. The Dodgers shelled out the money; they got an injured pitcher that turned into the highest paid reliever in the history of their ballclub. He ended up retiring early because of injuries.

December 12, 2000 – Mike Hampton, 8 yrs $121MM by the Colorado Rockies
What it got: 56-52, 4.81 ERA, 891.1 IP, 4.62 K/9, 1.25 K/BB
Bad move #2 for the Rockies this off season. Hampton was horrible; in fact, the only way they could trade him was part of a 3 way deal, where they (and the Marlins) took on a lot of the contract. The Rockies are off the hook this season for the deal. It also cost the team Juan Pierre to deal him.

January 16, 2001 – Chan Ho Park, 5 yrs $65MM by the Texas Rangers
What it got: 33-33, 5.56 ERA, 563 IP, 6.54 K/9, 1.57 K/BB
It was between retaining Dreifort or Park. Park was passed over, but the Rangers made sure he was a large payday. Park was one of the worst pitchers in the game, and the Rangers moved him in a salary dump to the Padres. He was decent with the Padres, but still not a $13MM a year pitcher. After the deal expired (and a year in the Mets organization), he came full circle and pitched for the Dodgers this season (for the league minimum).

April 1, 2001 – Bobby Higginson, 5 yrs $35MM by the Detroit Tigers
What it got: 1928 AB, 53 HR, .258/.343/.402
This was a big time extension forced on the GM by the owner. Higginson had a good year the previous season and was a homegrown player; ownership felt he was due this contract. Unfortunately, he never played to that level again and fans were forced to suffer through his performance for the full 4 years.

December 11, 2004 – Russ Ortiz, 4 yrs $33MM by the Arizona Diamondbacks
What it got: 7-22, 6.94 ERA, 227 IP, 4.64 K/9, .94 K/BB
A career as an OK pitcher sure gets someone a huge payday. Ortiz signed a deal that the D’Backs instantly regretted. He was traded after the season to the Orioles, and was released before the end of the deal. He latched back on with the Giants before being out of work again. The contract would have finished this year.

December 15, 2004 – Richie Sexson, 4 yrs $50MM by the Seattle Mariners
What it got: 1863 AB, 106 HR, .244/.332/.472
I’m still at a loss how a player that missed the previous season with a serious shoulder injury got a massive deal. Sure, Sexson has (or had) power; how could you be sure that he still had it after the injury. Seattle found out he still had the power, but couldn’t maintain a decent average. They hoped for the best, but ended up releasing him this past season. The Yankees used him for a few games, then also discarded him.

December 19, 2004 – Edgar Renteria, 4 yrs $40MM by the Boston Red Sox
What it got: 2218 AB, 44 HR, .292/.350/.417
Renteria left the Cardinals because he felt disrespected that they didn’t offer him the extra $1MM that the Red Sox did; it was the Sox’s mistake. Renteria was awful in Boston and was shipped to Atlanta after a season. His time in Atlanta wasn’t horrible, but his defensive short comings were shown when he wasn’t playing next to a third baseman with good range. Moved back to the AL this past off-season, Renteria again regressed and look like a shell of his former self.

December 20, 2004 – Carl Pavano, 4 yr $40MM by the New York Yankees
What it got: 9-8, 5.00 ERA, 145.2 IP, 4.63 K/9, 2.50 K/BB
Pavano broke out in 2004 and received a giant contract from the team he beat in the World Series. Instead of the ace that he looked like during his last season with the Marlins, Pavano was not very good. Most of the poor performance can be attributed to injuries, which is really why this contract was bad. His injuries also made his teammates question his motivation and drive to win. He’s currently back on the open market.

December 23, 2004 – J.D. Drew, 5 yrs $55MM by the Los Angeles Dodgers
What it got: 746 AB, 35 HR, .284/.397/.505
This wouldn’t be on the list if they didn’t have the opt out clause that Drew used to get a deal with the Red Sox. They should have made it that only the team could opt out of the deal, a la Ivan Rodriguez and the Tigers. Instead, he bolted and they had nothing to show for his 2 years in L.A. Toronto will be in the same position with AJ Burnett.

November 22, 2006 – Juan Pierre, 5 yrs $44MM by the Los Angeles Dodgers
What it got so far: 1043 AB, 1 HR, .290/.325/.344
Last year, they knew this was a bad signing. This year, they were forced to sit him (at least for cost controlled talent). It was so bad that they tried to move him with top prospects just to get him off the team (they offered him and Andy LaRoche for Scott Rolen to the Cardinals). They are essentially pay $9MM a season for a lead off hitter that stuggles to get on base. The only way he’ll be gone is to eat the contract.

December 8, 2006 – Jason Schmidt, 3 yrs $47MM by the Los Angeles Dodgers
What it got so far: 1-4, 6.30 ERA, 25.2 IP, 7.70 K/9, 1.57 K/BB
You’ll notice that the Dodgers are listed here alot. Schmidt was paid a lot of money to be a full time DLer. At least this was a 3 year deal; imagine if they would have offered the 5-6 years a lot of teams give pitchers.

December 13, 2006 – Julio Lugo, 4 yrs $36MM by the Boston Red Sox
What it got so far: 831 AB, 9 HR, .247/.314/.343
Boston has had problems signing shortstops – could they have the curse of Nomar? First, Renteria bombs. Next, Alex Cora can’t hit. Now, they have Lugo signed to a large deal. He’s been pushed to the bench by Jed Lowrie, but the Red Sox will probably have trouble moving him and the large sum of money he’s stealing.

December 19, 2006 – Kei Igawa, 5 yrs $20MM plus $26MM posting fee by the New York Yankees
What it got so far: 2-4, 6.65 ERA, 71.2 IP, 6.65 K/9, 1.43 K/BB
After losing out on Dice-K, the Yanks felt they needed to throw money at any Japanese pitcher they could get. So after securing the rights to talk to Igawa for $26MM, they gave him a huge deal. I guess they don’t remember the last time they had a Japanese pitcher in their rotation.

December 29, 2006 – Barry Zito, 7 yrs $126MM by the San Francisco Giants
What it got so far: 21-30, 4.83 ERA, 376.2 IP, 6.00 K/9, 1.36 K/BB
The current reason why you don’t give a pitcher a long term deal. Zito has been horrible after his move across the Bay. He spent time in the bullpen this year, which essentially made him the most expensive reliever in the history of the game. He did move back to the rotation, but it was more for lack of other options than performance.

There were some that were close to being added, but, outside of the Schmidt deal, all of these were at least 4 year deals. Andruw Jones is the best example – he’s getting a ton of money, but the Dodgers only gave him 2 years. It was partially to show that 2007 was a fluke.

Outside of a few hitters (A-Rod, Pujols), no player should get contracts that run guaranteed for 5-8 years. Injuries make long term deals too questionable for a team, especially for pitchers. I also don’t know why players with 1 good year get some of the deals that they do (aka Carl Pavano).

Some of the numbers above don’t look horrible, but you have to remember there were some major injuries; imagine Mo Vaughn’s or Albert Belle’s numbers if they don’t get hurt. Kevin Brown’s were pretty good prior to injury.

I guess no matter what, signing baseball players can be risky; some teams are just better at assessing the risk than others.