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As your mind reels at the size of Prince Fielder's payday, take a look at this list of 10 free-agent deals that didn't work out well for the teams that handed them out, which originally ran on February 20, 2007.

Enough big-money contracts were given to free agents this past offseason to make anyone's head spin. Barry Zito and Carlos Lee became beneficiaries of two of the only 14 nine-digit contracts in baseball history. The Giants lured Zito across the bay from Oakland for seven years and $126 million, while the Astros got Lee, the slugging left fielder and Panamanian cattle rancher, to stay in-state by signing him away from the Texas Rangers for six years and $100 million. In all, nine free agents signed contracts worth at least $45 million despite the class of available players being considered below average. However, the deals given to Zito and Lee were as much head scratchers as head spinners.

While Zito is seemingly coming into the prime of his career at 28, he has been on a downward trend since 2004. In his first four major-league seasons from 2000-03, Zito was 61-29 with a 3.12 ERA in 119 starts, and boasted nine-inning rates of 7.2 hits, 10.9 baserunners, 7.2 strikeouts, and 3.4 walks. Over the past three seasons, Zito went 41-34 with a 4.05 ERA in 103 starts and his nine-inning rates were 8.3 hits, 12.5 baserunners, 6.6 strikeouts, and 3.7 walks. PECOTA doesn't expect Zito to suddenly transform back into the pitcher who went 22-5 and won the American League Cy Young Award in 2002, projecting mediocrity in his next five seasons. Most telling is that PECOTA projects Zito's worth, in terms of MORP, from 2007-11 to be $34 million. Conversely, the Giants will be paying him $80 million in that span.

Lee is two years older than Zito at 30, and his numbers have been much steadier. He posted a .300/.355/.540 line in a combined 161 games last season with the Milwaukee Brewers and Texas while hitting 37 home runs and driving in 116 runs. However, Rangers pitchers were said to be frustrated by his statuesque range in the field late last season, and many scouts fear the 6-foot-2, 240-pound Lee is getting so big that he will soon be unable to play in the field. That's not a good thing for a National League team like the Astrosthey won't be able to make him their designated hitter. PECOTA expects Lee to continue to be a fairly steady producer over the next five seasons, but as in Zito's case, MORP doesn't jibe with the Astros' checkbook, valuing Lee's contributions at $44,050,000 from 2007-11 while Houston will be paying him $80.5 million during that time (including the prorated share of his signing bonus).

Thus, it would appear both the Giants and Astros will regret these contracts in those final years before they expire. As we'll explore in a bit, history is littered with free-agent contracts that matured into albatrosses, but the question is: Why do teams continually sign players to such long-term deals? Mainly, because the contracts look like good deals at the time, but there is also a human element involved, especially with general managers always being more concerned with the present and keeping themselves employed, rather than worrying about five years down the road.

In the Giants' case, they have been enveloped in the Barry Bonds/BALCO controversy for seemingly forever, and even many of their fans have grown worried about all the controversy. Thus, the Giants felt the best way to energize the fan base was to sign a charismatic star in Zito, who was familiar to Bay Area fans. "This was a definite want and need on the part of our ballclub," General Manager Brian Sabean said. "On a whole, everybody in the organization, including the players, are beside themselves for what this means for the organization."

The Astros' motivation for signing Lee is that they have been down a power hitter the past two seasons after Jeff Bagwell's chronic shoulder problems rendered him helpless at the plate and in the field, eventurally forcing him to retire after sitting all of last season. Thus, they looked more at what Lee could do for them now than that he might weigh 290 pounds in 2010. "Drayton McLane showed he is stepping up in a big way to answer a big question for our ballclub," Astros manager Phil Garner said the day the contract was signed.

While only time will tell if the odds are defied and the contracts for Zito and Lee work out, here is one man's list of the 10 worst contracts of the free-agent erawith a huge assist from Baseball Prospectus' NeildeMausealong with the clubs' rationale for handing out such large deals:

1. Mo Vaughn, Anaheim Angels
The contract: six years, $88 million, signed in December, 1998
Statistics before: .304/.394/.542 with 230 home runs and 752 RBI in 1,046 games in eight seasons.
Statistics after: .267/.356/.481 with 98 home runs and 312 RBI in 466 games in four seasons.

After failing to make the playoffs for 12 straight season and finishing just three games behind the Rangers in the American League West in 1998, the Angels felt they were close enough that one player could put them over the top. "When we embarked on this offseason, we decided we wanted to be real specific about the kind of players we wanted," Angels General Manager Bill Bavasi said. "Only the best would do. We think we've done that, with the addition of Mo." That idea certainly looked good in theory, as Vaughn had established himself as one of the most dangerous hitters in the game during eight seasons with the Boston Red Sox, including hitting .337/.402/.591 with 40 home runs and 115 RBIs in 154 games in 1998.

However, the signs were clear from the start that the big first baseman might not be meant to work out well for the Angels, as he sprained his ankle on Opening Night in 1999 when he fell into the dugout chasing a foul pop. Though Vaughn had two decent seasons in Anaheim, hitting a combined .276/.362/.503 with 69 homers and 225 RBI in 300 games, he missed all of the 2001 after undergoing surgery to repair a ruptured tendon in his arm.

Vaughn was traded to the New York Mets that offseason, and was never the same, hitting a combined .249/.346/.438 with 29 homers and 87 RBI in 166 games in two seasons, and then being forced to retire in 2003 when he could not overcome a serious knee injury.

2. Mike Hampton and Denny Neagle, Colorado Rockies
Hampton's contract: eight years, $121 million, signed in December, 2000
Statistics before: 85-53, 3.44 ERA with 8.8 hits allowed, 6.1 strikeouts, and 3.5 walks per nine innings in 241 games, 187 starts, and eight seasons.
Statistics after: 53-48, 4.80 ERA with 10.2 hits allowed, 4.7 strikeouts, and 3.7 walks per nine innings in 134 starts and five seasons.
Neagle's contract: five years, $51 million, signed in December, 2000
Statistics before: 105-69, 3.92 ERA with 9.0 hits allowed, 6.3 strikeouts, and 3.5 walks per nine innings in 320 games, 221 starts, and 10 seasons.
Statistics after: 19-23, 5.57 ERA with 9.9 hits allowed, 6.6 strikeouts and 3.3 walks per nine innings in 72 games, 65 starts, and three seasons.

The Rockies had been in existence for eight seasons and, except for winning the National League wild card in strike-shortened 1995, had never found the key to winning at high elevation. The Rockies had tried to win with speedsters, and win with power hitters. Following the 2000 season, they decided to try to win with pitching, and stunned everyone in baseball by lavishing $173 million on Hampton and Neagle, a pair of left-handers with fine track records. Hampton had been 15-10 with a 3.14 ERA in 33 starts for the pennant-winning Mets in 2000, while Neagle combined for a 15-9 record with a 4.52 ERA in 34 games (33 starts) for the Cincinnati Reds and New York Yankees.

"I did a lot of homework," Hampton said. "I was up late at night and early in the morning. I was going over teams position by position, looking at who's behind me (in the field) and who's going to be on the same pitching staff. This team is going to win. I firmly believe it. With the addition of myself and Denny Neagle and the confidence the bullpen has, we can get better and improve."

It didn't happen. Hampton and Neagle, like so many before and after, failed to learn how to get hitters out in Denver's thin air. Hampton went 21-28 with a 5.75 ERA in 62 starts while bothered by groin and foot injuries in two seasons with the Rockies, and was then shipped to the Braves along with $49 million to cover part of his remaining salary in a complicated three-way trade that also involved the Florida Marlins. Hampton's contract finally expires this season, as he tries to return after missing last season because of reconstructive elbow surgery.

Neagle also struggled throughout most of his time with the Rockies, had effectively career-ending reconstructive elbow surgery following the 2003 season, and then had to work out a buyout after being charged with soliciting a prostitute in December, 2004.

3. Chan Ho Park, Texas Rangers
The contract: five years, $65 million, signed in December, 2001
Statistics before: 80-54, 3.80 ERA with 7.6 hits allowed, 8.4 strikeouts, and 4.3 walks per nine innings in 221 games, 176 starts, and eight seasons.
Statistics after: 33-33, 5.56 ERA with 9.9 hits allowed, 6.5 strikeouts, and 4.2 walks per nine innings in 102 games, 98 starts, and five seasons.

The Rangers finished last in the AL West standings and last in the league earned run average in 2002. Thus, it stood to reason that they went into that offseason looking to sign a frontline pitcher, and they felt they'd found their No. 1 starter in Park, who had gone 15-11 with a 3.50 ERA in 36 games (35 starts) for the Dodgers the previous season. "He's the ace we've been looking for," Rangers first baseman Rafael Palmeiro said.

That turned out to be about as true as Palmeiro's declaration in front of a Congressional committee that he never used steroids. Park strained a hamstring in his first start for the Rangers and that led to a litany of disabled list stints that included time lost to finger, back, and rib cage injuries. Park went a combined 22-23 with a 5.79 ERA in 68 starts before the Rangers finally cut bait during the 2005 season and traded him to the San Diego Padres. He missed significant time again last season because of internal bleeding, and will try to resurrect his career with the Mets this spring after signing a one-year contract as a free agent guaranteeing him just $500,000.

4. Albert Belle, Baltimore Orioles
The contract: five years, $65 million, signed in December, 1998
Statistics before: .296/.368/.577 with 321 home runs and 1,019 RBI in 1,237 games and 10 seasons.
Statistics after: .289/.374/.509 with 60 home runs and 220 RBI in 302 games and two seasons.

Belle exercised an escape clause in his contract with the Chicago White Sox, and the Orioles, looking to get back to the playoffs after qualifying in 1996 and 1997 before slipping to fourth place in the AL East in 1998, were quick to jump on adding his bat to their lineup. The slugging outfielder felt the Orioles had a better chance of winning after he missed the postseason in both of his seasons with the White Sox. "You look at the situation the last two years, October rolls around and you're out there working on your golf game. That just didn't sit well with me," Belle said. "It was a situation where I weighed all my options and I felt Baltimore was my best option." Belle didn't help get the Orioles back to the postseason, though, and made it through only two years of his contract before a hip injury forced him to retire. The Orioles, meanwhile, are currently on a streak of nine straight losing seasons.

5. Darren Dreifort, Los Angeles Dodgers
The contract: five years, $55 million in December, 2000
Statistics before: 39-45, 4.28 ERA and 10 saves with 8.6 hits allowed, 7.8 strikeouts, and 3.8 walks per nine innings in 188 games, 87 starts, and six seasons.
Statistics after: 9-15, 4.64 ERA and one save with 8.3 hits allowed, 9.7 strikeouts, and 4.7 walks per nine innings in 86 games, 26 starts, and three seasons.

The Dodgers took a leap of faith when they signed Dreifort to his big contract, believing he had plenty of upside as a 28-year-old who had yet to live up to the stature of being the No. 2 overall pick in the 1993 draft behind Alex Rodriguez. "This guy has the potential to be a No. 1 starter," Dodgers General Manger Kevin Malone said. "You're really paying for the 'come,' for the future. When you get into postseason play, a guy like this can dominate a game." Dreifort never dominated in October, and never made it to the end of his contract, as he missed the 2002 season because of reconstructive elbow surgery, then was forced to retire following the 2004 season because of hip and knee injuries.

6. Jeff Bagwell, Houston Astros
The contract: five years, $85 million, signed in December, 2000 that served as extension beginning in 2002
Statistics before contract was signed: .305/.417/.552 with 310 home runs, 1,093 RBI, and 167 stolen bases in 1,476 games and 10 seasons.
Statistics after contract took effect: .277/.382/.496 with 100 home runs, 306 RBI and 24 stolen bases in 513 games and four seasons.

Along with teammate Craig Biggio, Bagwell had clearly become one of two Mr. Astros by 2000, and owner Drayton McLane needed to do something to win the fans back after the club had slipped to 72-90 following three straight NL playoff appearances. Of course, it wasn't Bagwell's fault that the Astros' playoff streak ended, as he'd hit .310/.424/.615 with 47 homers and 132 RBI in 159 games that season. That got McLane thinking about the day Bagwell might be inducted into the Hall of Fame, especially since Nolan Ryan had entered Cooperstown in a Texas Rangers' cap. "What happened with Nolan Ryan changed this franchise in negative ways,"McLane said. "Jeff came here in 1991 at a time when nobody knew who he was, and he has done things in his career that rank him alongside the greatest players in baseball."

However, Bagwell's career had started sliding into the decline phase once the contract went into effect in 2002. Though he combined to hit .278/.384/.503 with 97 homers and 287 RBI in 474 games in the first three seasons of the deal, chronic shoulder injuries limited him to only 39 games in 2005, though he did return to serve as the designated hitter in two games in the Astros' first World Series appearance, a sweep at the hands of the White Sox. Bagwell's shoulder did not respond well from the surgery, forcing him to miss all last season, and leading to his retirement this past winter.

7. Ken Griffey Jr., Cincinnati Reds
The contract: nine years, $116.5 million, signed in February, 2000.
Statistics before: .299/.380/.569 with 398 home runs, 1,152 RBI and 167 stolen bases in 1,535 games and 11 seasons.
Statistics after: .272/.361/.530 with 165 home runs, 456 RBI, and 11 stolen bases in 699 games and seven seasons.

It had the makings of a great story, the superstar outfielder tiring of being so far away from home, and giving the OK to be traded to his hometown Reds in a blockbuster deal just before the start of spring training, and just months after they'd lost to the Mets in a one-game playoff for the NL wild card. "This is something I dreamed about as a little kid, being back in my hometown where I watched so many great players," said Griffey, whose father was an outfielder regular on the Big Red Machine's World Series winners in 1975-76.

For a year, it was a great story, as Griffey hit .271/.387/.556 with 40 homers and 118 RBI in 145 games. Then Griffey's body started breaking down, and he has had only one remotely Griffey-like season since, posting .301/.369/.576 numbers with 35 homers and 92 RBI in 128 games in 2005. During his time with the Reds, Griffey has undergone surgery on a knee, hamstring, and ankle, and hasn't been to the postseason. The Reds are considering moving Griffey from center field to right this spring in an effort to keep him healthy; this comes after Griffey broke his hand in January while playing with his children.

8. Kevin Brown, Los Angeles Dodgers
The contract: seven years, $105 million, signed in December, 1998
Statistics before: 139-99, 3.30 ERA with 7.9 hits allowed, 9.0 strikeouts, and 1.7 walks in 314 games, 312 starts, and 11 seasons.
Statistics after: 72-45, 3.43 ERA with 8.2 hits allowed, 7.7 strikeouts, and 2.3 walks in 172 games, 164 starts, and seven seasons.

This was the original nine-figure contact, and that a team would invest in such a long deal with a 33-year-old pitcher stunned baseball people in the Opryland Hotel in Nashville during the 1998 winter meetings. Kevin Malone defended the deal, noting "I think Kevin is unique and special in the regard that he is without question the most durable pitcher in the major leagues. Kevin Brown is one of those special players who is capable of elevating a team into a championship team."

Brown lived up to his durability tag during for his first tow and a half seasons, posting a 41-19 record with a 2.77 ERA in 87 starts before undergoing non-Tommy John invasive elbow surgery. He struggled in 2002, going 3-4 with a 4.81 ERA in 17 games (10 starts), but bounced back strong in 2003, posting a 14-9 record and sparkling 2.39 ERA in 32 starts. The Dodgers used his comeback to get out from under the contract by trading him to the Yankees that winter. Brown was a respectable 10-6 with a 4.09 ERA in 22 starts in 2004, then slipped to 4-7 with a 6.50 ERA in 13 starts in 2005. At that point, his career was over, as he drew no interest on the free-agent market.

9. Carl Pavano, New York Yankees
The contract: four years, $39.95 million, signed in December, 2004
Statistics before: 57-58, 4.21 ERA with 9.5 hits allowed, 5.9 strikeouts, and 2.6 walks per nine innings in 167 games, 149 starts, and seven seasons.
Statistics after: 4-6, 4.77 ERA with 11.6 hits allowed, 5.0 strikeouts and 1.6 walks per nine innings in 17 starts for Yankees in 2005.

Pavano said he realized his lifelong ambition when he put the Yankees' pinstripes on the first time at an introductory press conference three days before Christmas in 2004. "I've been playing baseball since I was seven years old, I always dreamed of playing for the Yankees," Pavano said. "If I passed up the opportunity to play with the very best franchise in all of sports, I think I would have regretted that."

Pavano's dream has been a nightmare and it's been the Yankees who have had regrets for signing him. He's not pitched since June 27, 2005, sitting out the last season and a half because of elbow, shoulder, back, and buttocks injuries. while also suffering two broken ribs in an automobile accident while in the minor leagues on an injury rehabilitation assignment last season. Though Pavano's teammates have questioned his desire to pitch through pain, he spent the winter working out in Arizona, and the Yankees are counting on him to hold down a spot at the back end of their rotation this season. However, it seems much longer than three years ago that Pavano had his breakthrough season, going 18-8 with a 3.00 ERA in 31 starts for the Florida Marlins.

10. Wayne Garland, Cleveland Indians
The contract: 10 years, $2.3 million, signed in December, 1976
Statistics before: 27-18, 3.00 ERA with 8.1 hits allowed, 4.4 strikeouts, and 2.7 walks per nine innings in 91 games, 33 starts, and four seasons.
Statistics after: 28-48, 4.50 ERA with 10.2 hits allowed, 3.5 strikeouts, and 2.9 walks per nine innings in 99 games, 88 starts, and five seasons.

Yes, $2.3 million seems like a misprint in our era of baseball economics, but the Indians hadn't won an American League pennant in 22 years, and dove headfirst into the first winter of free agency by making Garland the third-highest paid player in the game, behind future Hall of Famers Reggie Jackson and Catfish Hunter. It was a case of Garland being at the right place at the right time, as he had followed three undistinguished seasons as a swingman for the Orioles with a breakout year in 1976, going 20-7 with a 2.67 ERA in 38 games and 25 starts, while making a whopping $23,000.

Garland had a decent debut season with a bad Indians team, going 13-19 with a 3.60 ERA in 38 starts in 1977, but then he tore his rotator cuff the next season. He was never the same after the shoulder surgery, and the Indians released him following the 1981 season with five years left on his contract. The contract remains Garland's ignominious claim to fame. "No matter where I am, it still comes up," Garland told the Cleveland Plain-Dealer in a 1997 story. "It will be that way until the day I die."

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Other than A-Rod's original 10 year with Texas which long term contracts HAVE worked out well ? I'm just curious, some
teams must have gotten good dollar value from their investments. I'm calling 6 years or more long term, just to pick a number.
Pujols for 8/$116 when the Cards extended him in 2004 was obviously money well spent.

And though he's slipped a bit lately, David Wright for 6/$55m or 7/$70m is great value, even acknowledging that some of that bought out arbitration years.

Chase Utley at 7/$85 is a great deal even given the time he's missed in the past few years.

Longoria's deal is going to be great value for the Rays in a few years.

Basically, extending your players to buy out arbitration years works out a lot better than making long-term commitments to players closer to 30 than 20.
I think the Red Sox have to be happy with the Manny contract which was 8 years, $160 million.
Miguel Cabrera is four years through a 8n yr/$152.3M deal, and that one looks like it will work out fine seeing as though he's already given the Tigers something like $100M worth of value in those four years.
Jeter's 10 year deal was fine.
Dave Winfield signed an eight year deal with the Yankees if I remember right, and he was pretty good for them.

That's just 8+ year contacts, I'm sure there are some more six year deals that worked out fine.
Wasn't Winfield's a 10 year deal? Plus some personal services and foundation money that they fought over at the end?
All of these players appear to have struggled with injuries. That's fine, but that's the risk of any long-term contract. What makes these contracts the WORST? When did the team just spend big on a complete lemon?
Barry Zito can't be too far down the list
Sorry. I should actually read the article prior to commenting. At work, and skipped right to the list (which was fun and interesting)
After Garland signed, he called his mom. An article at the time quoted him as saying something like "Mom, I didn't get the $1 million I was looking for. I GOT $2 MILLION!"
I remember reading this (and enjoying it) when it was first published. Nice to see some entertaining old pieces getting brushed off.

Will y'all be putting up some of the seminal pieces such as McCracken's BABIP article (I assume you will)?
Russell, we republished that article as part of the Wayback series in March. We've been trying to alternate evergreen research pieces like that one with old articles that can be tied more closely to current events. You can also get a double dose of the classics in our two-volume Best of Baseball Prospectus collection.
Great, thanks! I must have missed it.
I don't remember Kevin Malone, but he sure seems to be an idiot.
This story is a great read. Even better would be the legends behind the stories. For instance, it's a great part of baseball lore that Babe Ruth was sold by Boston to the Yankees to finance "No! No! Nanette!", a Broadway musical. Not only does this help to explain why a baseball team would make a seemingly catastrophically bad decision, but it even rubs salt in the wound. Are there any great stories out there other than "The Giants admired Barry Zito from across the Bay and decided they needed to another Barry". All rational fans thought Zito should have topped out at $85 million. What prompted the Giants to overpay by $40 million?

PS - thanks for the Wayne Garland quote--
"And this will be the O's 9th straight losing season". -- Quotes from 2006

Now where's that bottle of whiskey? Oh right, Lee Evans dropped it.