*Jay quoted Baseball Prospectus's WARP, which puts Crawford's contributions at 0.7 wins above replacement; I'll be using Baseball-Reference's WAR (bWAR), which puts him at 0.4, a negligible difference.
First, a few ground rules. The contracts in question must be at least four-years (long-term) and have a total value of at least $20 million (big money). Among other things, that helps eliminate some of the bizarre, decade-long contracts from the early days of free agency that had average annual values at or below a million dollars. It also restricts us to contracts that are hard to get rid-of. A bad three-year contract, for example, can be dumped after just two bad seasons.
Also, for my primary list, I'm going to only include contracts that have reached their fourth year. So, Crawford and other recent signees are not yet eligible, though I'll show you where he'd fall on the list after I present it. For the active contracts that are included below I calculated the cost per win above replacement using a pro-rated three-fourths of their 2012 salary.
Update: Thanks to Leonardo Ordaz Guía in comments below and Twitter follower Stefan V. for pointing out that Carlos Silva and Aaron Rowand, respectively, are missing from the list below. Silva should be third, having delivered -1.3 WAR after signing a four-year, $48 million contract with the Mariners after the 2007 season. Silva falls in the category of players whose contracts were unmotivated, as he had gone 24-29 with a 5.01 ERA (87 ERA+) for the Twins in the two seasons before general manager Bill Bavasi brought him to Seattle. The Mariners traded rotten apples with the Cubs after the 2009 season, flipping Silva and the final two years of his contract (minus $9 million that Seattle covered) for Milton Bradley. Both teams lost that trade. Silva, who was healthy enough to throw just 30 1/3 innings in the second year of his contract due to a shoulder injury, made just 21 more starts after the trade and didn't pitch in the majors at all in the final year of his deal, nor has he since.
Rowand contributed just 1.9 bWAR to the Giants over the first four seasons of the $60 million, five-year contract he signed in December 2007, earning his release in early September of that fourth season. He has not appeared in the majors this year and will come in at $31.58 million per win above replacement if he finishes the year without adding to his total. Rowand signed that contract after hitting .309/.374/.515, making his only All-Star appearance, and winning the Gold Glove for the Phillies in 2007, but was never so much as an average hitter in San Francisco. It's amazing that the Giants were able to win it all in 2010 with both Rowand and Zito on the books.
Contract: $65 million/five yearsbWAR: -0.6$/bWAR: N/A
My research produced three contracts that fit my above criteria and yielded a negative bWAR. Of those three, Park's was the most expensive, thus earning the top spot on this list. Park, the first Korean-born major leaguer, excelled for the Dodgers prior to becoming a free agent after the 2001 season. He was an All-Star that year and in the last two seasons before his free agency averaged 16 wins, 218 strikeouts and a 3.38 ERA (122 ERA+), but the move from pitching-friendly Dodger Stadium to the homer-happy Ballpark In Arlington didn't agree with him.
Park also suffered from a variety of ailments, from the pedestrian (hamstring strain, blisters) to severe (back problems that limited him to seven starts in 2003 and a life-threatening intestinal issue in 2006). Banking on their friendlier ballpark, the Padres sent Phil Nevin to Texas for Park at the trade deadline during the fourth year of his deal, but he was no better for them. His ERA+ in 68 starts for Texas: 83; in 30 starts and four relief appearances for San Diego: 79.
Contract: $50 million/five yearsbWAR: -1.3$/bWAR: N/A
There were some who worried about Park's transition when he signed with Texas, but I'm not sure anyone outside of the Angels' organization ever thought Gary Matthews' contract was a good idea. Matthews signed his contract after hitting .313/.371/.495 as the Rangers' centerfielder in 2006 and making a homer-robbing catch that people still talk about, but prior to that season he had hit .249/.327/.397 across parts of seven major league seasons and he was 32 when he accepted the Angels' offer.
Matthews' line in his first season in Anaheim was closer to that previous career mark and it just got worse from there. To their credit, the Angels immediately realized their mistake, signing Torii Hunter the following offseason, pushing Matthews to the bench and ultimately paying the Mets $22.3 million to take him and the remaining $23.4 million of his contract prior to 2010, the fourth year of his deal. Matthews played just 36 games for New York before earning his release that June, failed to play his way back to the majors with the Reds organization later that year and spend the fifth year of his contract in a forced, but well-paid retirement.
Contract: $33 million/four yearsbWAR: -3.5$/bWAR: N/A
Purely in terms of performance, the return the Diamondbacks got on their investment in Ortiz was the worst on this list. In the four years (2000-03) prior to signing with Arizona before the 2004 season, Ortiz averaged 17 wins and a 3.71 ERA (111 ERA+) for the Giants and Braves, but he was so bad for the Diamondbacks (5-16, 7.00 ERA in 28 starts with more walks than strikeouts) that they cut him in the middle of the second year of his deal, eating the $17.75 million he was owed over the next two years just for the privilege of getting him off the roster.
Ortiz subsequently resurfaced with the Orioles, Giants, Astros and Dodgers but didn't throw as many as 90 innings with any of those teams and was never close to being even an average pitcher again.
Contract: $55 million/five yearsbWAR: 0.0$/bWAR: N/A
Dreifort's contract was another that seemed utterly unmotivated. In three years as a starting pitcher for the Dodgers prior to signing his five-year deal in Dec. 2000, Dreifort was an almost perfectly average pitcher. His ERA+ was 98, he was one game below .500 and his peripherals were all right around league average. Yet, what made his contract a disaster wasn't so much the Dodgers' misjudgment of his abilities as his own inability to take the ball. Over the five years of his contract, Dreifort threw just 205 2/3 innings, made just 26 starts and 60 relief appearances (the latter all in 2004, the fourth year of the deal), and missed all of the second (Tommy John surgery) and fifth years (knee and hip surgery), after which he never returned to the major leagues.
Contract: $39.95 million/four yearsbWAR: 0.3$/bWAR: $133.17 million
Pavano was sort of a cross between Matthews and Dreifort. Save for his walk year in 2004 (18-8, 3.00 ERA, 137 ERA+ for the Marlins) he had never excelled in the major leagues in seven previous, injury-pocked seasons, and after he signed with the Yankees he spent more time on the disabled list than on the mound. From 2005-08, Pavano made just 26 starts and threw only 145 2/3 innings with the team, and he missed all of 2006 due to a back injury and made just two appearances in 2007 before undergoing Tommy John surgery.
His bWAR line above comes from his first 17 starts with the Yankees in his first season with the team (4-6, 4.77 ERA). After that he managed just nine more over the next three and a half years. Adding insult to injury, he then averaged 214 innings per season with the Indians and Twins in the first three years after his contract expired.
Contract: $121 million/eight yearsbWAR: 1.8$/bWAR: $67.22 million
Hampton's contract is remembered for the injuries that plagued him in the second half of it (he started just 25 games and threw just 147 1/3 in the second four years of the deal, missing the 2006 and 2007 seasons entirely). Yet, over the first four years (2001-04) he averaged 30 starts and 186 innings a season. The trouble was, he wasn't any good.
Hampton "earned" his contract with fine seasons for the Astros and Mets in pitching-friendly ballparks in Houston and Queens, but it only took two years and a 5.75 ERA (88 ERA+) for the Rockies to realize their mistake. After the 2002 season Colorado orchestrated a complicated three-team trade that sent Hampton to the Braves via the Marlins and managed to get the Marlins to help Atlanta pay his contract by taking on the salaries of catcher Charles Johnson and outfielder Preston Wilson. Hampton started to right his ship in Atlanta, where he posted a 106 ERA+ in 2003 and 2004, but then his elbow gave out. He missed all of 2006 and 2007 due to injuries and made just 44 more appearances before retiring after the 2010 season.
Contract: $80 million/six yearsbWAR: 1.5$/bWAR: $53.33 million
This is the contract that most likely to haunt Tigers general manager Dave Dombrowski's nightmares. Much like the hefty Prince Fielder, currently playing very well in the first year of a nine-year, $214 million contract with Detroit, Vaughn was a corpulent, superstar first-baseman in his 20s and a perennial MVP candidate who earned a huge contract. Vaughn, the 1995 AL MVP with the Red Sox, saw his production plummet when he left Fenway Park after the 1999 season (from a 148 OPS+ in his last six seasons there to a 117 OPS+ in his first two seasons in Anaheim), after which his body began to break down.
The ruptured bicep that cost him the entire 2001 season may have been a fluke, but the Angels knew better. They flipped him to the Mets, who got one more 114 OPS+ season out of him in 2002 before his knees gave out and ended his career at age 35 in 2003, the fifth year of his contract.
Contract: $51 million/five yearsbWAR: 1.0$/bWAR: $32 million
Like Hampton, Neagle signed with the Rockies before the 2001 season and the two lefthanders combined to give Colorado the worst offseason in major league history. They were part of the Rockies' plan to sign changeup specialists based on the theory that breaking balls didn't break in Denver's thin air (a theory since disproven by more scientific methods than Neagle and Hampton's failures).
Neagle, who was awful in the second half of the 2000 season with the Yankees, posted a 5.32 ERA (95 ERA+) in his first two years in Colorado. Then, in 2003, his elbow gave out in June, requiring Tommy John surgery, after which a combination of age (he was 34 at the time of the injury), poor performance and bad off-field behavior prevented his return to the major leagues. However the last of those, which came in the form of an arrest for solicitation in 2004, allowed the Rockies to void the last year and option buyout on his contract under a morals clause, eliminating $19 million of their debt and thus reducing their cost per win above.
Contract: $126 million/seven yearsbWAR: 3.9$/bWAR: $24.17 million
Zito, who won the Cy Young award for Oakland in 2002, is in the sixth year of this contract and has gone 52-69 with a 4.53 ERA (91 ERA+) for the Giants. That he was healthy and left off the postseason roster when they won their first West Coast world championship in 2010 tells you almost all you need to know about his importance to the team.
Contract: $126 million/seven yearsbWAR: 4.7$/bWAR: $16.76 million
Contract: $136 million/eight yearsbWAR: 5.7$/bWAR: $16.75 million
Wells' contract got two general managers fired: the Blue Jays' J.P. Ricciardi, the man who signed Wells to the deal back in 2008, and the Angels' Tony Reagins, who inexplicably traded for Wells prior to the 2011 season, sending Mike Napoli to the Blue Jays in the process. I'm oversimplifying a bit (Reagins technically resigned and there were certainly other factors that led to both men's dismissals), but not much. Wells, who is still owed $21 million each of the next two seasons, is now an expensive extra outfielder for the Angels, who were doing better when he was on the disabled list.
Soriano had a 40/40 season for Washington prior to signing his deal with the Cubs as part of Chicago's spending spree after the 2006 season. He has since almost completely stopped stealing bases and he was never particularly good at getting on base or fielding. He has hit .251/.308/.468 over the past four seasons while averaging 23 homers, five steals and $18 million in salary.
That's a litany of misery. So where would Crawford fall on that list? Here are the five big-money, long-term contracts from the last three years that are off to the worst starts:
There's still hope that Dunn (the major league home run leader this season), Howard (who is in the first year of his five-year extension) and Crawford (who has five years left after this one) can provide some return on their team's investments. The other two seem likely to become permanent residents on this list. Lackey is missing this entire season due to Tommy John surgery and has just two years left on this deal, and Bay, whose pact expires after next season, has hit just .235 in three injury-plagued years for the Mets.