Carlos Delgado’s contract expires at the end of this season, and opinion is divided on whether the Blue Jays will be able to re-sign him at that time. Whether he stays or goes, however, no one but Carlos, his agent and their immediate families will be saddened by the expiration of that deal, signed as baseball’s turn-of-the-century spending frenzy approached its end. In case you’ve forgotten, the contract paid him $14.8M in 2001, $17.2M in 2002, $17.5M in 2003 and $18.5M in 2004.

Many Toronto fans have since bemoaned this contract, at length. But if you don’t think the Jays got off easy, you haven’t been keeping an eye on the rest of baseball.

Delgado’s deal was for just four years, his prime production period, for the going market value at that time. He was a young, handsome, popular, homegrown player on the verge of superstardom, and he would have made at least that much elsewhere. True, injuries and the general organizational malaise of the late Ash Era hurt his production, but he played every day, contributed what he could and generally reserved his complaints for certain members of the press corps.

Now imagine if Carlos had been signed not for four years, but for ten; not for a maximum of $18.5M , but for millions more per year, every year. Now imagine if he’d suffered health or off-the-field problems that seriously hurt his production, or if he played a key defensive position terribly, or if he became a clubhouse distraction or even a cancer.

Those nightmare scenarios befell several teams over the past few years, the ones who weren’t lucky or smart enough to dodge the bullet that Gord Ash, to his credit, dodged in the winter of 2000. When the free-agent bubble burst a season or two ago, the Blue Jays were in a relatively good position, with Delgado’s contract the only albatross on the books and already half complete. Thanks to the good work of JP Ricciardi in dumping bad contracts held by stalwarts like Raul Mondesi and Alex Gonzalez, Delgado’s deal is the only major one left, and at the end of September, it’s done.

So cheer up, Jays fans: things could have been a lot worse. How much worse? That’s what we’re here to find out.

Today, we’re going to look at five truly ugly contracts and five organizations (well, four really) that, when the millionaire musical chairs game ground to an unexpected halt, were left without seats. We’re going to decide: what is the worst player contract in baseball?

The rules are simple: rank the following five contracts in terms of their heinousness. I’ve suggested a few criteria, but you can choose your own:

· total money payable
· total length of contract
· foreseeability of trouble at time of signing
· irresponsibility of contract in the context of the team’s overall vision

You’re allowed to use 20/20 hindsight if you wish -– the contract wouldn’t have been so bad if such-and-such hadn’t happened -- but part of offering a good contract is being able to envision the reasonable foreseeability of injury, decline, local market conditions and so forth.

Ready? Here are your five candidates, listed alphabetically. Voting will take place on a 10-7-5-3-1 point scale, so remember to rank all five contracts. Votes will be tabulated when I can get around to it. All figures courtesy of the Bluemanc contracts Website; all ages as of July 1, 2004.




1. Mike Hampton, LHP, 31

Eight years, $121 million

2001: $8.0M
2002: $8.5M
2003: $11.0M [ATL $2.0M / FLA $9.0M]
2004: $12.0M [ATL $2.0M / FLA $10.0M]
2005: $12.5M [ATL $1.5M / FLA $11.0M]
2006: $13.5M
2007: $14.5M
2008: $15.0M
2009: Team option $20.0M or $6.0M buyout
(Plus $20.0M signing bonus deferred until end of contract)

The story goes that a prominent sabrmetrician advised Dan O’Dowd that a superior sinkerball pitcher like Hampton would flourish in Coors Field. Half a season into this gigantic contract (the biggest in baseball at the time), O’Dowd and his advisors looked like geniuses: Hampton had a 9-2 record, an ERA in the 2.00s, and was seriously being talked about as a Cy Young candidate. We all know what happened afterwards: utter implosion, as Hampton became the worst starting pitcher in baseball for the next year and a half.

The Rockies did extricate themselves from their disaster, at least partially: they dealt Hampton to the Marlins for two shorter yet also egregious contracts, those belonging to Preston Wilson and Charles Johnson. The Braves then worked a nice piece of chicanery, acquiring Hampton for Tim Spooneybarger and basically half of Hampton’s remaining contract. Hampton was pretty decent for Atlanta last year and will probably remain so for the next few seasons. But the Marlins can’t complain either: they rid themselves of a lot of long-term obligations, picked up superb leadoff man Juan Pierre from the Rox, and got themselves a World Series championship to boot.

Overall, Hampton’s was probably the least painful of the contracts from a purely financial point of view, since the cost was spread out among three teams. But that doesn’t mean the deal was any less awful when it was signed (you gotta love that deferred signing bonus at the end, like the tail of a rattlesnake). And it’s not like this was the only mistake Dan O’Dowd made. Consider …



2. Todd Helton, 1B, 30

Nine years, $141.5 million

2001: $5.0M
2002: $10.6M
2003: $10.6M
2004: $11.6M
2005: $12.6M
2006: $16.6M
2007: $16.6M
2008: $16.6M
2009: $16.6M
2010: $16.6M
2011: $19.1M
2012: Team option $23.0M or $4.6M buyout

Unlike Hampton, no one could question Todd Helton’s credentials before his contract. He was one of the best young hitters in the game, powerful and destructive even away from Coors Field. A near-miss contender for the Triple Crown in 2000, Helton signed this contract before the 2001 campaign, a deal that would keep him a Rockie until he was 38. Could anyone have foreseen the back troubles that would spring up the following year, sapping some of his power and cutting his home run totals from 42 and 49 in ’00 and ’01 to 30 and 33 the last two seasons? Or that the good people of Denver would finally tire of the Rockies’ losing ways and stay away from Coors Field in droves, depriving the franchise of its cash cow’s money flow? Or that the decade-long Mardi Gras of a spending spree that had gripped baseball would come to a crashing halt?

Even with a sore back, Helton still has tremendous value today, and he’s still in the prime of his career. But word has it that the Rockies are shopping his contract with a persistence bordering on desperation, as the franchise seeks to redefine itself as a small-market team. Trouble is, there are very few teams out there willing to take on that kind of money, and they’re not particularly interested in adding a contract that will expire the same year Britney Spears turns 30. Dan O’Dowd succeeded in making Mike Hampton someone else’s problem; he may yet do the same with Helton.



3. Derek Jeter, SS, 30

Ten years, $189 million

2001: $11.0M
2002: $13.0M
2003: $14.0M
2004: $17.0M
2005: $18.0M
2006: $19.0M
2007: $20.0M
2008: $20.0M
2009: $20.0M
2010: $21.0M
(Plus $16.0M signing bonus paid over 8 years)

There’s perceived value, and there’s actual value. The perceived value of Derek Jeter in February 2001 was off the charts. There was some good reason for that: he had just posted 40 HRs and 40 steals over the previous two seasons combined, batting .349 and .339 with excellent plate discipline in those campaigns. But there was a lot of perception that didn’t accord with reality, starting with the belief that Jeter was an outstanding defensive shortstop. Then there was his cult-icon status in New York City, his rock-solid clutch-hit reputation in the playoffs, his Mariah Carey-level celebrity grade, and his heartthrob status that to this day remains something of a mystery to me. One national columnist wrote that Nomar Garciaparra had to look up and squint in order to see Derek Jeter. That was the environment in which the shortstop could sign a $189M contract that some people actually referred to at the time as a “hometown discount.”

Real value, of course, is a little different. Today, it’s not just sabrmetricians who know that Jeter has the worst range of any shortstop in baseball, and that “Mr. Clutch’s” career batting line of .314/.385/.469 in nearly 400 post-season at-bats is indistinguishable from his .317/.389/.462 overall lifetime numbers. Today, Jeter has had two straight average seasons (one of which, in fairness, came courtesy of Ken Huckaby), a trend that shows no sign of reversing as this middle infielder approaches his mid-30s. Today, there’s a vastly superior shortstop playing to Jeter’s right, a situation that everyone connected to the Yankees must quietly be recognizing hurts the team. The reality is that Derek Jeter is terribly overpaid for what he produces on the field, a situation that will only worsen over the length of his contract. But will anyone in New York face up to that?



4. Manny Ramirez, LF, 32

Eight years, $160M

2001: $13.0M
2002: $15.5M
2003: $18.0M
2004: $20.5M
2005: $20.0M
2006: $19.0M
2007: $18.0M
2008: $20.0M
2009: Team option $20.0M
2010: Team option $20.0M
(Plus $16.0M signing bonus paid over 5 years)

In the winter of 2000, a lot of bad decisions were being made by a lot of people, many of them associated with firms like Arthur Andersen and Tyco. But baseball team executives should not be left off this list. At the 2000 winter meetings, the Boston Red Sox desperately wanted free agent Mike Mussina to anchor their rotation; instead, he signed a six-year, $88.5M contract with the hated Yankees. So how did Dan Duquette respond? He did the equivalent of getting back at the nice girlfriend who dumped you by marrying the local flibbertigibbet. He signed Manny Ramirez, a tremendous hitter with a fragile temperament, to a contract two years longer and an incredible $71,500,000 richer. The Cleveland Indians presumably still have Duquette on their Christmas card list.

We all know what’s happened since, of course. Relations between the Red Sox and Ramirez deteriorated to the point where they simply placed him on waivers, hoping that someone named George might pick up the contract where they dropped it. No such luck, which led to trade discussions with the Rangers, which led to all sorts of bad things happening to Red Sox Nation. Despite his status as an overwhelming offensive force, Ramirez’s contract, as has been proven this past off-season, is literally untradeable. Manny is a one-dimensional player ― although, what a dimension― and no team is willing to take on his idiosyncrasies unless most of his salary obligations remain behind in Boston. Is it the worst deal in Red Sox history? Short of the one that helped finance No, No, Nanette, yes, it is.



5. Alex Rodriguez, 3B, 29

Ten years, $252 million

2001: $21.0M
2002: $21.0M
2003: $21.0M
2004: $21.0M
2005: $25.0M
2006: $25.0M
2007: $27.0M
2008: $27.0M
2009: $27.0M
2010: $27.0M
(Plus $10.0M signing bonus paid between 2001-2005)

A-Rod’s presence, of course, hangs over this contest like a cloud. In his own way, he’s a central player in discussions of the Jeter and Ramirez contracts, and I’m sure you’ve been thinking about him from the first paragraph of this feature. Rodriguez, even more so than Helton, is at the top of his game: he has the rare distinction of being among both the best offensive and the best defensive players in baseball. Unlike the others, he’s still in his 20s (barely), and continued excellence can be expected from him for many years to come (indeed, the move to third base might actually help prolong his career somewhat).

But there’s no escaping the fact that A-Rod’s was the ultimate contract, in the literal sense that the likes of it cannot be seen happening again in North American professional sports. “One quarter of a billion dollars” is a phrase that simply doesn’t belong in personal services contracts, yet there it is, in the total value column of the albatross that nearly sank the Texas Rangers. Rodriguez is a Yankee now, on one of only two teams that could have afforded his contract, giving New York a left side of the infield that approaches half a billion dollars in total value. But when the Steinbrenner Era passes, as it almost certainly will during the length of these deals, how soon will it be before these contracts, and especially A-Rod’s, begin weighing down even this mighty franchise?

The one thing that all these deals have in common is that they’re hot potatoes: whichever team owns the contract last will come to regret it. The Braves won’t be happy about the tens of million they’ll be paying to an aging junkballer at the end of the decade. The Rockies are probably still calling around about Helton’s deal, while the Red Sox have presumably resigned themselves to having Manny’s contract in the fold till the day he retires. Will the Yankees retain both of their out-of-position infielders to the bitter end? It says here that if they can unload one or both someday, they’ll do it.

These are five hottest potatoes in baseball; but which burns the worst? That’s your call.