Trying to make a big splash in free agency automatically risks making a big mistake. While this winter’s shopping season has been especially strange because of the way in which the economic situation has had an impact on who signs where and for what, it’s interesting that most teams haven’t made the mistake of offering too many long-term contracts for pitchers, a reflection of the increasing certainty that anything beyond three years can go from million-dollar expense to millstone on the payroll lasting years beyond that bit of off-season impulse buying had seemed like such a good idea. Nevertheless, spend some teams did, and regrets they will most certainly have, but who did the worst? Let’s break this into different categories: the worst one-year, two-year, and three-year contracts, with honorable mentions in each category, and capped by the worst deal of the winter for its length, expense, and likely return.

Worst One-Year Contract: Trevor Hoffman, Brewers, $6 million

There was a lot of action involving closers changing places this past winter, but you can rely on the Brewers to keep throwing money at the problem in their joyless pursuit of a reliever who might merit a seven-figure payday. Ever since Derrick Turnbow‘s control vacated the premises during 2006, they tried trading for Francisco Cordero only to watch him walk away after 2007, rented Eric Gagné for 2008 at the hefty cost of $10 million only to watch skipper Ned Yost burn out the fragile former All-Star early on, and have now decided to pile a subsequent risk on top of that one by giving the fading future Hall of Famer a chance to spin his wares far from the wide-open spaces of Petco Park. With little to keep lefties honest any more, and without the benefit of the game’s best pitcher’s park to provide an assist, the changeup fiend might have to switch from AC/DC’s “Hell’s Bells” to “Back in Black,” to at least celebrate his reward for almost certainly closing out his career as a Brewer. What happened to the wisdom that conjured up Turnbow, or before him Danny Kolb, and then avoided getting too involved with either? As the transient utility of Turnbow or Kolb or even Salomon Torres last year substituting for Gagné demonstrated, you can assign save opportunities for all sorts of people and get perfunctory effectiveness; spending top dollar for falling stars can go Tunguska on you both on the payroll and on the diamond.

Honorable Mention: Jason Varitek, Red Sox, $5 million.
Alex, can I buy a ‘C’ for $5 million? It takes an awful lot of faith in one player’s intangibles to look past last year’s equally intangible production at the plate and spend a very tangible number of clams on a player who isn’t a better option than any of the less-expensive alternatives in camp, starting with Josh Bard, but also including George Kottaras and Dusty Brown. Add in concerns over Varitek’s ability to deter the running game, and that’s a lot to pay for a former famous person.

Worst Two-Year Contract: Willy Taveras, Reds, $6.25 million

The problem with signing Willy Taveras has little to do with the total expense; it’s not zero dollars down, but in baseball terms it’s not really all that expensive. It has even less to do with the things that he does do well, like run and steal bases (generating a NL-best 11.9 Equivalent Baserunning Runs), covering the gaps, throwing pretty effectively for a center fielder). The problem is what Taveras is being employed to do-lead off-and the chance that he can deliver on it with even a modicum of effectiveness. His park-neutral PECOTA projection for 2009 is for a .319 OBP, which doesn’t sound too good for a team that got a .326 OBP from its weak crew of leadoff options last year. The real pity is that the Reds could have instead run with a platoon that puts sophomore Chris Dickerson in center and leading off-Dickerson’s projected to a park-neutral .331 OBP, which he’d surpass if his minor league splits held in the majors and he was limited to starting versus righties. And no, employing Dickerson wouldn’t cost “only” $6.25 million the next two years-money that might have instead been spent on getting a left fielder who might actually help the Reds score some runs.

Honorable Mention: Aaron Miles, Cubs, $4.9 million.
While Jim Hendry’s desire to deal with his lineup’s heavy lean to the right was commendable, did it really have to involve spending this kind of money for a mediocre defender who projects to “contribute” a .238 Equivalent Average, well below last year’s position averages at short (.255) and second (.264)? Miles’ replacement-level production is the sort of luxury item most teams should forgo, especially when there are utilitymen knocking around the minors who cost less, and especially when the Cubs could have simply stuck with the since-dealt Ronny Cedeño in the role for less, and gotten better glove work and more upside for their troubles.

Worst Three-Year Contract: Raul Ibañez, Phillies, $30 million

OK, now we’re talking real money, the sort of cash that you might think gets Congress yammering about limiting executive pay in the boardrooms of baseball as well as banking. By striking early into his tenure and inking Ibañez a couple of weeks into December, newly minted Phillies general manager Ruben Amaro completely failed to anticipate the shape of this winter’s market, as younger and arguably better players like Adam Dunn, Bobby Abreu, and-that’s right, Phillies fans-Pat Burrell all got less money over shorter contracts, costing their employers just a combined $41 million for five player seasons. Amaro also radically overspent to bring a DH-to-be in his age-37 through age-39 seasons to the National League: PECOTA’s long-term forecasting valued Ibañez’s next three seasons at $13.5 million in marginal value over a replacement-level player (MORP), and that’s without any special accounting for this winter’s frozen market place. While the Phillies had to make a call one way or another, offering Burrell arbitration or a deal like the one he signed with the Rays, or waiting out the market to bring Ibañez’s value down toward where Dunn and Abreu signed would have been the much smarter play than that early bit of headline-grabbing.

Honorable Mention: Milton Bradley, Cubs, $30 million.
Technically, this could wind up being a two-year deal for $18 million, with 2011 being either a club option for $12 million or a $2 million buyout if Bradley’s persistent health woes bite the Cubs in 2009 or 2010. This isn’t to bang on Hendry overmuch-somebody was going to take the risk on Bradley’s health, but like the Phillies with Ibañez, by buying earlier in the winter and spending top dollar for a down-ballot MVP-caliber DH, the Cubs have added a lot of risk with few guarantees. The relative expense of the Angels‘ bringing in Bobby Abreu (one year, $5 million) goes to show that balancing out the Cubs’ righty-hitter-heavy lineup didn’t have to go this steep for this long, and while the upside risk is pretty tasty, Bradley’s history is such that it’s a tough bet to take or make.

Worst Contract of the Winter: A.J. Burnett, Yankees, five years, $82.5 million

Without signing the occasionally healthy and occasionally valuable Burnett, the Yankees’ rotation would feature CC Sabathia, Joba Chamberlain, Andy Pettitte, and Chien-Ming Wang. So why spend $16.5 million per year for the next five on a pitcher with Burnett’s spotty track record? Well, because you can, I suppose, and because somebody else you’re competing with might, but is investing this kind of money in a pitcher coming off of just his second full season in a big-league rotation in ten in The Show really where you want to wind up? Between Burnett’s repeated problems with durability and consistency over the course of his career, the money alone for this kind of length was nuts. Add in that young pitching is the organization’s great strength-Phil Hughes representing just the front end of the wave-and short-term deals like Pettitte’s incentive-driven one-year contract look entirely sensible as an adaptation to the market and the team’s immediate win-now needs; Burnett’s deal, by comparison, does not. Consider this the white elephant that’ll make Yankees fans forget Carl Pavano.