Worst Contracts in MLB History
Owners around baseball continue to sign off on lucrative, multi-year deals for players for what amounts to a really expensive game of chicken.
At one end of the street sits the owner in his half-a-million dollar Rolls Royce Phantom, with a newly-signed acquisition in the passenger seat.
At the other end of the street, in a rusty, beat-up, lime green Ford Pinto, sits Father Time, with Lady Luck riding shotgun and the injury bug squished between the seats and the hatch.
More often than not, one car swerves just in time, avoiding a major catastrophe.
But every once in a while, both sides get cocky—and the carnage that ensues is difficult to watch.
These are some of the results of those wrecks. Be warned—what follows is not for the faint of heart.
Unless otherwise noted, all statistics courtesy of Baseball-Reference.com.
1999: Mo Vaughn Signs with the Anaheim Angels
Like Eric Cartman, Vaughn was "big-boned."
Harry How/Getty Images
The Contract: Six years, $80 million
Stats During Contract: 466 G, .267/.356/.481, 98 HR, 312 RBI
Mo Vaughn hit the free-agent market heading into the 1999 season on the heels of a successful run in Boston. From 1993 through 1998, Vaughn hit .315 while averaging 36 home runs and 110 RBI per season, firmly establishing himself as one of the premier sluggers in the game.
Angels manager Terry Collins could hardly contain himself when he spoke to reporters shortly after the deal, one that made Vaughn the highest-paid player in the game, was announced.
The signing of Mo Vaughn is an extraordinary event for our ballclub. Mo is one of those rare individuals whose presence will have a profound effect on the players, the organizations and this community. Our ownership has established its desire to take this team to the next level, and Mo is the type of individual who relishes that challenge.
He wasn't terrible over his first two years with the Angels, hitting .276, while averaging 34 home runs and 112 RBI.
But Vaughn was 31 years old, and given his physical attributes, his body simply couldn't handle the girth, generously listed at 225 pounds. Surgery to repair a damaged left biceps muscle and tendon would cost him the entire 2001 season, and things went downhill from there.
His weight began spiraling out of control, and by the time Vaughn was healthy enough to return to action in 2003, he found himself a member of the New York Mets, traded for veteran starter Kevin Appier.
Vaughn's body simply couldn't hold up, and issues with his knees would ultimately end his career after playing in 166 games over a two-year span with the Mets, hitting .249 with 29 home runs and 87 RBI.
2001: Darren Dreifort Re-Signs with the Los Angeles Dodgers
Batters circled the bases routinely against Dreifort.
Jeff Gross/Getty Images
The Contract: Five years, $55 million
Stats During Contract: 86 G (26 starts), 9-15, 4.64 ERA, 1.45 WHIP, 221 Ks, 205.2 IP
Three months trumped seven years in the case of Darren Dreifort and the Los Angeles Dodgers.
Dreifort, who had gone 39-45 with a 4.28 ERA and 1.38 WHIP over parts of seven years with the Dodgers, parlayed a three-month stretch at the end of the 2000 season into a lucrative payday.
Over the last three months of the 2000 season, Dreifort went 8-2 with a 3.43 ERA and 96 strikeouts in 99.2 innings of work.
That was enough for the Dodgers to pay him $11 million a season at the age of 32, ignoring his mediocre career and history of arm trouble.
Trouble is exactly what the Dodgers got, as Dreifort managed only 16 starts in 2001 before having his elbow reconstructed, surgery that cost him all of the 2002 season as well.
He made only 10 more starts for the Dodgers, going 4-4 with a 4.03 ERA in 2003 before arm and leg injuries began to take their toll. Dreifort returned as a middle reliever in 2004 but was ineffective with a 4.44 ERA and 1.56 WHIP.
Injuries cost him the 2005 season as well, and he was retired by the age of 32.
2001: Mike Hampton Signs with the Colorado Rockies
Hampton's time with the Rockies was...wait for it...rocky.
Brian Bahr/Getty Images
The Contract: Eight years, $121 million
Stats During Contract: 147 starts, 56-52, 4.81 ERA, 1.54 WHIP, 458 Ks, 891.1 IP
Heading into the 2001 season, 28-year-old Mike Hampton was the best pitcher available via free agency—and the Rockies rewarded him with what was the biggest contract in the game at the time.
Over the previous four seasons, Hampton had gone 63-31 with an ERA of 3.30, averaged more than 220 innings pitched per season, and successfully kept the ball on the ground, something Colorado figured would play well in the thin air of Coors Field.
Rockies GM Dan O'Dowd was ecstatic with the addition, telling reporters, "We added a horse. His leadership in the clubhouse will be very important for us in the next eight years."
The horse lasted only two years in Colorado before being put out to pasture.
In 62 starts for the Rockies, Hampton went 21-28 with a 5.75 ERA, 1.68 WHIP and issued nearly as many walks (176) as strikeouts (196).
Prior to the 2003 season, Hampton was traded twice: first by the Rockies to the then-Florida Marlins, then two days later by the Marlins to the Atlanta Braves.
Hampton gave Atlanta two decent years (18-12, 4.06 ERA in 41 starts) before injuries cost him both the 2006 and 2007 seasons.
He would appear in only 44 games after that for the Braves, Houston Astros and Arizona Diamondbacks before retiring prior to the 2011 season.
2001: Todd Hundley Signs with the Chicago Cubs
Hundley failed to follow in his father's footsteps with the Cubs.
Jonathan Daniel/Getty Images
The Contract: Four years, $23.5 million
Stats During Contract: 192 G, .198/.289/.398, 30 HR, 77 RBI
His father Randy spent a decade behind home plate at Wrigley Field, so it was only fitting that Todd Hundley followed in his father's footsteps.
The Cubs needed an everyday catcher and a powerful bat to put in the middle of the lineup for the 2001 season, and Hundley, on paper, appeared to offer both.
While there was some power, the 32-year-old Hundley simply couldn't handle major league pitching anymore, striking out nearly 35 percent of the time that he stepped to the plate.
Somehow, the Cubs managed to convince the Los Angeles Dodgers to take Hundley—and the two years remaining on his deal prior to the 2003 season—getting back a pair of veterans in Eric Karros and Mark Grudzielanek.
2001: Denny Neagle Signs with the Colorado Rockies
There wasn't much to smile about during Neagle's time in Colorado.
Brian Bahr/Getty Images
The Contract: Five years, $51.5 million
Stats During Contract: 65 starts, 19-23, 5.57 ERA, 1.47 WHIP, 271 Ks, 370.1 IP
Denny Neagle was confident, almost cocky, heading into Colorado, and who could blame him? A ground-ball pitcher heading into a home-run haven, Neagle had more than 50 million reasons to be full of himself.
I'm certainly not afraid to pitch in Coors Field. It doesn't take a rocket scientist to know that this is not one of the better pitcher's parks, but I hope to change that perspective.
There was a time when Coors Field was intimidating for me. You have to get over that mental factor. You can't come to this ballpark and think, 'Gosh, here we go, a Coors Field start.' It's the same thing when you pitch at Wrigley Field with the flags blowing straight out. You accept that. And if you get over that mentally, then the physical part follows. I think that's why I learned to pitch and be effective in this park.
Unless Neagle has a different definition of the word "effective" than the rest of us, that simply wasn't the case.
He'd go 10-10 with a 5.77 ERA in 31 starts at Coors Field, but the truly damning thing was that his performance on the road wasn't much better, sitting with a 9-13 record and 5.36 ERA.
Neagle would last throw a pitch for the Rockies in July 2003, missing the rest of that season and all of 2004 with elbow problems. Upon his arrest for soliciting a prostitute in suburban Lakewood, the Rockies terminated the final year of Neagle's contract, ultimately ending his major league career.
2002: Chan Ho Park Signs with the Texas Rangers
Park is another Scott Boras client to make the cut.
Ronald Martinez/Getty Images
The Contract: Five years, $65 million
Stats During Contract: 68 starts, 22-23, 5.79 ERA, 1.61 WHIP, 280 Ks, 380.2 IP
After five consecutive winning seasons with the Los Angeles Dodgers, the Texas Rangers wasted little time in inking the 29-year-old Korean import to a lucrative, multi-year deal when he hit free agency prior to the 2002 season.
Owner Tom Hicks was excited to sign the contract, telling reporters "Finally, we have our No. 1 starter."
Not quite, Tom.
Park was anything but a front-of-the-rotation starter for the Rangers, never posting an ERA under 5.45 in any of his three-and-a-half years with the club.
In the middle of the 2005 season, the Rangers traded Park to the San Diego Padres for third baseman Phil Nevin in an exchange of overpaid, under-performing players, ending Park's tumultuous tenure in Texas.
2005: Russ Ortiz Signs with the Arizona Diamondbacks
Diamondbacks fans still have the occasional nightmare over this image.
Nick Laham/Getty Images
The Contract: Four years, $33 million
Stats During Contract: 28 starts, 5-16, 7.00 ERA, 1.90 WHIP, 67 Ks, 137.2 IP
Russ Ortiz had won at least 14 games each season since 1999 and logged at least 204 innings in all but one of those years. Considered one of the most consistent and durable pitchers in the game, it wasn't at all surprising that a team was willing to pay him well heading into the 2006 season.
Things started out well enough, as Ortiz would go 2-1 with a 3.60 ERA over his first five starts as a Diamondback, holding opposing batters to a .237/302/.395 slash line.
That was the extent of his success in the desert.
He would go 3-10 with an 8.05 ERA over his next 17 starts, missing nearly two months with a rib injury and finishing the season 5-11 with a 6.89 ERA.
Things didn't get any better in 2006, as he'd go 0-5 with a 7.54 ERA over his first six starts of the season before Arizona decided to bite the bullet, eat the $22 million remaining on his contract and release the 32-year-old, the most expensive "buyout" in the game at that point.
2005: Carl Pavano Signs with the New York Yankees
Pavano wasn't the only one scratching his head during his time in pinstripes.
Al Bello/Getty Images
The Contract: Four years, $38 million
Stats During Contract: 26 starts, 9-8, 5.00 ERA, 1.46 WHIP, 75 Ks, 145.2 IP
After tossing eight innings of one-run ball against the New York Yankees in Game 4 of the 2003 World Series, Carl Pavano was officially on the team's radar.
And after going 18-8 with a 3.00 ERA in 2004, the final year of his contract with the Florida Marlins, it was no surprise when Pavano wound up with the Yankees.
In only the second start of his Yankees career, Baltimore's Melvin Mora hit a screaming line drive back to the mound that smacked into Pavano's head, knocking him from the game in the third inning.
Things went downhill from there.
Pavano would make 17 of his 26 starts as a member of the Yankees in 2005, going 4-6 with a 4.77 ERA before rotator cuff problems would end his season before the All-Star break.
A myriad of injuries hit him in 2006, including injuring his buttocks during a spring training game and starting the season on the disabled list due to a back injury. He would feel discomfort in his right arm during a May rehab start and undergo surgery two days later to remove bone chips from his elbow.
In August, the Yankees found out that Pavano broke two ribs when he crashed his Porsche in Florida during his rehab from the elbow surgery. He'd miss the entire season.
Injury would once again rear its ugly head over the final two years of his contract, as Pavano would make a total of nine starts for the Yankees during the rest of his deal, pitching to a 5.52 ERA and becoming Public Enemy No. 1 in the Bronx, drawing the ire of both fans and teammates alike.
2006: Barry Zito Signs with San Francisco Giants
Zito has been far from the ace he was advertised to be.
Jonathan Daniel/Getty Images
The Contract: Seven years, $126 million
Stats During Contract: 178 G (172 starts), 58-69, 4.47 ERA, 1.40 WHIP, 701 Ks, 1,006 IP
With 102 wins, six consecutive seasons of 200 innings pitched and the 2002 AL Cy Young Award on his resume, Barry Zito was the hot free agent heading into the 2007 season.
It would take the richest contract for a pitcher at the time, but Zito took his electric curveball and crossed the Bay Bridge, leaving the Oakland A's and joining the San Francisco Giants.
When news of the deal first leaked, an unnamed Giants' source told Henry Schulman and Susan Slusser of the San Francisco Chronicle: "We view Zito as a franchise player, and we'll certainly need one when Bonds goes."
The Giants didn't get that franchise player.
Zito has been no better than a back-of-the-rotation starter since joining the Giants, and it wasn't until 2012—the next to last year of his deal—that Zito finished the season with a winning record, going 15-8 with a 4.15 ERA.
While Zito was solid in the regular season and playoffs, going 2-0 with a 1.69 ERA and 1.38 WHIP in three postseason starts, being a part of two World Series-winning teams doesn't make Zito's contract any better of a deal.
2007: Kei Igawa Signs with the New York Yankees
Igawa made Dice-K's deal look good.
Al Bello/Getty Images
The Contract: Five years, $46 million (includes $26 million posting fee)
Stats During Contract: 16 G (13 starts), 2-4, 6.66 ERA, 1.76 WHIP, 53 Ks, 71.2 IP
After watching their arch nemesis, the Boston Red Sox, ink Japanese superstar Daisuke Matsuzaka to a lucrative deal heading into the 2007 season, the New York Yankees did what any reasonable club would have done—they went out and signed their own Japanese pitcher, 27-year-old left-hander Kei Igawa.
He'd appear in 14 major league games during his rookie season of 2007, going 2-3 with a 6.25 ERA and 1.68 WHIP. Two more games in 2008, when he'd allow 13 hits and six earned runs over four innings of work, marked the end of his major league career.
Igawa would spend the rest of his contract as the most well-paid minor leaguer in the game.
He actually turned out to be a solid pitcher for the Triple-A Scranton/Wilkes-Barre Yankees, going 33-22 with a 3.81 ERA and 1.30 WHIP in 89 games (75 starts), but a major league pitcher he was not.
2007: Jason Schmidt Signs with the Los Angeles Dodgers
One of the few times the Dodgers saw Jason Schmidt in uniform.
The Contract: Three years, $47 million
Stats During Contract: 10 starts, 3-6, 6.02 ERA, 1.71 WHIP, 30 Ks, 43.1 IP
Coming off a six-year run with the San Francisco Giants that saw him make three NL All-Star teams, finish in the Top 5 of the NL Cy Young Award voting twice and go 78-37 with a 3.36 ERA, signing a soon-to-be 34-year-old Jason Schmidt heading into 2007 didn't seem like a risky move for the Los Angeles Dodgers.
GM Ned Colletti thought the Dodgers had pulled off a coup as the ink on Schmidt's new deal was drying.
Jason is a top-of-the-rotation starter who can dominate a game as well as any pitcher in the major leagues. He's a proven winner and that's something that's very hard to find.
After spending more than $15 million per win and nearly $5 million per start over three years in Los Angeles, Colletti was certainly singing a different tune by the time Schmidt's contract was up.
Shoulder problems plagued Schmidt throughout his Dodgers career, limiting him to six starts in 2007, costing him the entire 2008 season and ultimately ending his career after only four more major league outings in 2009.
2008: Andruw Jones Signs with the Los Angeles Dodgers
Jones was never a fit in Los Angeles.
Christian Petersen/Getty Images
The Contract: Two years, $36.2 million
Stats During Contract: 75 G, .158/.256/.249, 3 HR, 14 RBI
A 10-time Gold Glove winner and five-time All-Star, Andruw Jones was coming off of the worst season of his career as he hit free agency following the 2007 season.
The Dodgers, already with a crowded outfield that included youngsters Andre Ethier and Matt Kemp, decided to drop nearly $40 million on the veteran slugger.
Jones arrived to spring training out of shape and struggled to get going, hitting .165 with a pair of home runs and seven RBI through his first 43 games before a knee injury sidelined him for more than a month.
Upon his return, Jones continued to struggle, was out of a starting spot by the middle of August and found himself relegated to bench duty for the rest of the season.
Los Angeles wasted little time in cutting ties with him following the 2008 season, not interested in finding out what was in store for both parties in the second year of his deal.
2007: Gary Matthews Jr. Signs with the Los Angeles Angels
Matthews couldn't run away from high expectations.
Nick Laham/Getty Images
The Contract: Five years, $50 million
Stats During Contract: 406 G, .245/.322/.377, 30 HR, 169 RBI, 31 SB
After a breakout season in 2006 as a member of the Texas Rangers, hitting .313 with 19 home runs, 79 RBI and 10 stolen bases, the Los Angeles Angels decided to invest heavily in a 32-year-old outfielder with one season as a starter under his belt.
"He's a guy we're really happy to have," Angels general manager Bill Stoneman said during a conference call. "One of our objectives during this offseason was to improve ourselves in center field."
His first season in Anaheim wasn't terrible, as Matthews hit .252 with 18 home runs and 72 RBI, but things quickly deteriorated after that.
Over the next two seasons, he'd hit .245 with 12 home runs, 96 RBI and 12 stolen bases, becoming an offensive liability and one of the most expensive bench players in the game.
The Angels traded Matthews to the New York Mets prior to the start of the 2010 season, agreeing to pay all but $2 million of the $23.5 million that remained on his contract.
He'd hit .190 with a RBI in 36 games for the Mets before his time in New York was complete.
2008: Alex Rodriguez Re-Signs with the New York Yankees
A-Rod's laughing all the way to the bank.
Jonathan Daniel/Getty Images
The Contract: 10 years, $275 million
Stats During Contract: 620 G, .282/.370/.503, 129 HR, 447 RBI, 53 SB
In the fall of 2007, Alex Rodriguez was coming off of his second AL MVP-winning season in four years and was well on his way to becoming baseball's all-time home run king.
In a move that only seems like a good idea to people totally in love with themselves, Rodriguez and agent Scott Boras decided that Game 4 of the 2007 World Series was the appropriate time to announce that A-Rod was opting out of the 10-year, $252 million deal he was playing under.
Rodriguez would go around both Boras and Yankees GM Brian Cashman, negotiating a new contract with Hank and Hal Steinbrenner, who by this time had taken control of the franchise as their father, George, saw his health continue to deteriorate.
Now, it's true that the first three seasons of this deal were solid ones for Rodriguez and that the New York Yankees would not have won the 2009 World Series without his contributions.
But that simply doesn't make up for the dead fish that Rodriguez has become—and to whom the Yankees will be paying big money through the 2017 season.
Since signing the contract, Rodriguez has been involved with two PED scandals, admitted to doping during his days with the Texas Rangers and become one of the most reviled athletes in all of sports, not just baseball.
He's also become injury-prone, requiring surgery on both hips, the latest of which is expected to keep him out of action until after this year's All-Star break.
Rodriguez hasn't played more than 138 games in any season since signing the deal, and he's averaged only 110 games over the last two years.
His chase of Barry Bonds and Hank Aaron atop the career home run list has become essentially worthless to everyone except Rodriguez, who stands to make an extra $30 million on top of his salary if he continues to climb the charts.
The Yankees owe Rodriguez a $6 million bonus for each of five milestones that, at the time of the deal being signed, were thought to be historic milestones: tying the home run marks of Willie Mays (660), Babe Ruth (714), Hank Aaron (755) and Barry Bonds (762) and breaking Bonds' major league record.
A-Rod and his contract have become the most untradeable assets in baseball. The Yankees would take a corned beef sandwich from the Carnegie Deli in exchange for him, but there isn't a general manager alive who wouldn't think they were overpaying in that deal.
2008: Carlos Silva Signs with the Seattle Mariners
Silva was never worth the money Seattle agreed to pay him.
Otto Greule Jr/Getty Images
The Contract: Four years, $48 million
Stats During Contract: 57 G (55 starts), 15-24, 5.82 ERA, 1.49 WHIP, 159 Ks, 296.2 IP
A mediocre pitcher throughout his major league career, you can't fault Carlos Silva for signing the lucrative, multi-year deal that the Seattle Mariners offered him heading into the 2008 season.
Silva took the money, and Seattle got what it paid for: a mediocre starting pitcher who, in reality, wasn't even mediocre.
He was just bad.
Silva would go 4-15 with a 6.46 ERA in 28 starts that first season in Seattle. The following season was even worse, as he appeared in only eight games—six of them starts—going 1-3 with an 8.60 ERA.
Seattle, desperate to move Silva, found a willing trade partner in the Chicago Cubs, who had grown tired of outfielder Milton Bradley, who was overpaid, outspoken and someone who had clearly worn out his welcome in the windy city.