Money Down the Toilet: MLB’s Worst Contracts

Catcher - Jorge Posada (NYY)

This was a close call with the O's Ramon Hernandez (due $8 million in 2009 and earning a scandalous $7.5 million this year) running Posada really close. What settled the debate was the sheer length of Posada's contract — he's in the first year of a four-year deal worth $52.4 million. Add in that he's currently under the knife, his season is over, has full no-trade protection, and it seems unlikely he'll ever be even an average catcher again and you have one of the worst contracts in baseball.

A lesson learnt for Brian Cashman — there's no room in baseball for sentiment. Posada should have been cut loose last year, despite the fans and local press calling for the Yankees to offer him the four years he wanted.

First Base - Todd Helton (COL)

Here's a good bumper sticker: Todd Helton — killing the Rockies since 2003. Nine years, $141 million and change — for a singles hitter. Helton is a good disciplined hitter and a thorough professional, but he's owed the best part of $60 million including his 2012 buyout and has full no-trade protection. No amount of clubhouse presence is worth that.

Second Base - Julio Lugo (BOS)

Okay, he doesn't actually play 2B for the Sawx, but as there's a lot of competition for worst shortstop contract he's moving over. He's probably a less-bad second bagger than he is shortstop, anyhow.

Lugo was supposed to be the answer at SS after the revolving door years in Fenway. Instead, he's an untradeable albatross and has been beaten out by the Alex Cora/Jed Lowrie tandem. For the $17 million he's earned by the season's end, Lugo has returned a season of .294 OBP hitting and been demoted to the bottom of the lineup, when he's actually healthy or not riding pine. Still owed $18 million plus an unlikely $9 million vesting option.

Third Base - Eric Chavez (OAK)

It's too easy to pick on A-Rod here with his ludicrous deal that pays him $25 million a year or so until he's old enough to need his food mashed and can't remember his own name. The fact is A-Rod puts up numbers and bums on seats.

A much worse contract is that of Eric Chavez of the (normally) fiscally-prudent A's. Chavez was a decent player a few years ago, but he's played 113 games since the start of the 2007 season and returned 17 home runs and 60 RBIs. He can't stay off the DL and is still owed $26 million following this year. If he ever shows he can a) stay healthy and b) hit above .500 SLG, he might be moveable, but it's a long shot.

Shortstop - Derek Jeter (NYY)

Wow, there's some serious competition here. Exhibit A is Jack Wilson of Pittsburgh, he of the career .375 SLG percentage and still owed almost $15 million through 2009. Exhibit B is 32-year-old Michael Young of Texas, who's owed $80 million through 2013 despite a serious decline in his numbers since 2005. The winner, however, is legendary Yankee captain and all-round sporting icon Derek Jeter, New York demi-god.

Jeter is owed $61 million for the 2008, 2009, and 2010 seasons. His OBP, SLG, and OPS have seriously declined since 2005 to such an extent that all three are at their lowest point since he first made the team full-time in 1996. His defense is dreadful. He hits into rally-killing double plays for fun. The clamor for another contract that sees him end his career in a Yankee uniform will start next year, as it did for Posada and Mariano Rivera last year. Brain Cashman should ignore it.

Outfield - Juan Pierre (LAD), Aaron Rowand (LAA), Vernon Wells (TOR), Gary Matthews, Jr. (LAA)

The Dodgers seem to have cornered the market in bad contracts (Pierre, Andruw Jones, Jason Schmidt) but Juan Pierre's is easily the worst. It runs until 2011, pays him $28.5 million for the next three years on top of the $15.5 million he's already earned. All this for a guy who's not worth a starting spot, can't throw, has no power (career .371 SLG), gets caught stealing more times than one-legged kleptomaniac, and gets on base at the same rate as Kelly Shoppach, Cleveland's mighty backup catcher.

Finding a bat to replace Barry Bonds isn't easy. Brian Sabean, not one of the games' brighter GMs, decided to turn to a man who'd never drove in 100 runs, had two seasons of 25-plus homers on his resume (both in hitter-friendly parks in Chicago and Philadelphia) and was an big injury risk.

To compound the error, Sabean, in a moment presumably clouded by alcohol, offered Aaron Rowand a five-year deal worth $60 million. He's a good defensive outfielder and an average hitter. $12 million a year is a lot to pay for that.

Vernon Wells can hit. He plays decent defense. He's a good guy. He also earns a heck of a lot of money — $126 million to be exact over the next seven years. Consider these numbers: 2011 $23 million: 2012, 2013, and 2014 — $21 million per year for a guy who will be 33-, 34-, and 35-years-old, respectively. He's not even 30 yet and can't stay healthy. This is the ultimate in albatross contracts for a franchise that simply can't afford them.

There are so many bad outfield contracts I added a fourth guy, which is appropriate as Gary Matthews, Jr. has the look of a bench player already, even though he's not even two years into a five-year, $50 million dollar deal.

Matthews, Jr. earned his deal on the strength of a few highlight-reel defensive plays in Texas, where he was an average (at best) hitter in a hitter-friendly ballpark. He's never hit 20 homers in a season, or drove in 100 runs. His career best SLG percentage is .495. He doesn't steal bases and has only hit over .300 once. His career OPS is .745. The only thing above average about this guy is his contract.

Designated Hitter - Travis Hafner (CLE)

He can't field. He can't stay healthy, despite hardly ever playing a position and only has to run the bases around 40% of the time. He can rake and owns a fantastic career OPS of .932, even with one down year on his resume.

Hafner is the ultimate conundrum. You don't want to lose him because he's so good, but you know he's fragile and you've heard the rumors of a "supplementary lifestyle." I can empathize with Mark Schapiro on the four-year, $57 million deal he gave Hafner. But it's not going to work out on the basis of his disastrous 2008. He's languishing on the 60-day DL and a lot of experts and scouts suspect this could be a regular gig. It's a shame because the guy's a talent.

Starting Pitching - Barry Zito (SF), Jeremy Bonderman (DET), Dontrelle Willis (DET), Carlos Silva (MIN)

There can be no other place to begin other than back in beautiful San Francisco, home of great architecture, a beautiful waterfront, a spectacular bridge, and Brian Sabean, our heroic drunken GM, prone to costly errors of judgment on a scale unimaginable even by Steve Phillips.

Barry Zito (SF) was a great pitcher in Oakland in 2002. He had a good year in 2003. Then he had three mediocre years and became a free agent. Sensible GMs, even though they craved lefty starting pitching, steered well clear of Barry and his agent Scott Boras, as they were asking for at least a six-year deal. Sober GMs know that long-term deals for pitching rarely work out well.

Fearless Brian knew that this was weak-kneed defeatism. He threw caution to the wind, knowing Barry Bonds' deal wasn't going to be renewed, so he had cash to (literally) burn, and blew away the (limited) opposition with a mind-boggling seven-year, $126 million contract that even Boras couldn't believe.

In one foul swoop, Denny Neagle, Mike Hampton, and Carl Pavano were consigned to the history books. This was the worst, most spectacularly stupid contract in baseball history.

Barry Zito LHP is the proud owner of a 5.80 ERA and a 1.80 WHIP. Brian Sabean is said to be considering trading Matt Cain for Juan Pierre when he checks out of the Betty Ford clinic.

Then there's Jeremy Bonderman (DET). RHP has always been what horseracing folk call a "talking horse." He's always on the verge of a great season. He's a 220-inning strikeout machine waiting to happen. He's a Cy Young winner one day, the stopper to-be at the head of the rotation, the soon-to-be intimidator that posts a sub-3.00 ERA.

The only problem is he's been in the league for six seasons and has never posted a sub-4.00 ERA for a full season. His career WHIP is a below average 1.39. Hitters aren't really intimidated by him — his career BAA is .268. He takes one step forward then follows it with two steps back. He has talent, but can't harness it, so much so that rumors of some of the front office being in favor of moving him in 2007 surfaced. He's owed $25 million over the next two years and has been paid $8.5 million for a wasted 2008.

Next is Dontrelle Willis (FL). Three years for $29 million dollars from 2008-2010 looked good if you ignore Dontrelle's disastrous 2007 in Florida. GM Dave Dombrowski chose to ignore a 200 IP, 5.17 ERA season in which Willis appeared to completely lose the little control of the strike zone he possessed.

Dombrowski is regretting that mistake to the tune of $22 million over the next two years. Willis is at Class A Lakeland and went a miserable 4.1 innings on Saturday. He has talent, but his mechanics are extremely suspect, his control has never been anything other than mediocre, and his peripherals have declined every year since 2005 (K/BB down, BB/9 up, H/9 up).

Finally, there's Carlos Silva (SEA). Bill Bavasi was finally fired in June as Mariners GM following a series of Sabean-esque blunders that left the season in the toilet by May. Not content with offering Miguel Batista a ridiculous deal (see below), he waved $48 million under Carlos Silva's nose for four years of less than average pitching.

Silva has one supposed good point — he doesn't walk many batters. That's primarily because batters find it so easy to hit him they don't need to wait for a walk to get on base. His career BAA is .301. He once walked a meager 9 batters in 188 IP and has made a career out of that stat. His current ERA is 5.62 and he's managed 4 wins. In the next three years, Silva will earn $35 million while the Seattle faithful boo lustily.

Relief Pitching - Miguel Batista (SEA)

Not much to write home about here except failed reliever, failed starter turned failed reliever again Miguel Batista in Seattle. He's due $18 million for 2008 and 2009, but can't hold a rotation spot on a very poor team. He can't get anyone out from the 'pen and got kicked out the rotation in June when sporting an ERA over 6.00. An outing in July against Cleveland summed up his season — 2 IP, 7 H, 8 R, 8 ER, and 1 HR.

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