Crawford's deal: Worst deal ever?

The turmoil enveloping the Boston Red Sox continues. On Friday, Red Sox principle owner John Henry had some choice words regarding the signing of Carl Crawford last offseason. Henry, in no uncertain terms, indicated the signing was not something he liked, telling a Boston sports radio station:

    "[Crawford was] definitely a baseball signing. In fact, anyone involved in the process, anybody involved in upper management with the Red Sox will tell you that I personally opposed that. They all know that."

While one can debate the merits of openly criticizing a player with whom you still have many years of necessary co-existence, there’s no question that the first year of the seven-year, $142 million contract was an epic failure. With the Red Sox and Crawford in the headlines and free agency not that far away, just how bad was Season No. 1 of Crawford’s contract? You can make a strong argument that it is the worst start to a deal of anywhere near this magnitude in free agency history.

In that last decade, there have been 18 free-agent contracts issued of at least $50 million in total value and $15 million in average annual value (please note: includes only free-agent contracts, not extensions). When you assess the net difference between the average annual value of the contract and what the player actually contributed in that first season, Crawford grades out as the worst -- and it’s not particularly close.

Here's a look at the worst returns in the first season of free-agent contracts with an average annual value of at least $15 million and total value of at leas $50 million, since 2001 (data from FanGraphs.com).

As one can see, Crawford’s return-on-investment is easily the worst in the past decade. Barry Zito’s seven-year, $126 million contract is often held up as the cautionary free agency tale, as Zito’s production never justified such a contract in the first place and he didn’t elevate his game upon signing with the Giants. He has not had a single season since joining the Giants where he justified his average annual value. Crawford’s return in the first year of his contract -- which is worth just over $2 million more per season than Zito's -- blows Zito’s out of the water.

Some of the other most-maligned contracts in MLB history appear on this list, including Jason Bay's deal with the Mets, Jayson Werth's from this past offseason with the Nationals and Carlos Lee's with the Astros. Carlos Beltran's first season with the Mets is often cited as one of the worst first-year performances after signing a free-agent deal in league history. Given that they are both athletic outfielders whose value, in part, is derived from their defense, Beltran seems like an apt direct comparison. But even Beltran's uninspiring start to his Mets career easily surpassed Crawford's first taste of the dirty water.

Carlos Beltran versus Carl Crawford, Year 1

Beltran: .266/.330/.414, 52 XBH, 2.7 WAR, +2 Defensive Runs Saved

Crawford: .255/.289/.405, 47 XBH, 0.2 WAR, -4 DRS

While Crawford was demonstrably worse in 2011 than Beltran was in 2005, Beltran posted a remarkable bounce-back season in 2006. In that season, he posted an MVP-caliber performance, complete with a 7.9 Wins Above Replacement mark that fully re-established his value as an impact player. Crawford certainly retains the skill set to put together a similar return to form, though we know that he’ll be attempting it without the complete support of Henry, the man who issued the contract that has started out as poorly as any big deal of the past decade. In fact, extending back even further and loosening the parameters a bit, there is only one contract since 1990 of at least $50 million total value (putting aside the AAV of $15 million requirement) to grade out worse in the first season: No, not Mike Hampton, not Kevin Brown ... but Adam Dunn deal with the White Sox, one which generated a stunning -$27.0 million return in 2011. Clearly, not good company for Crawford.

Justin Havens is a researcher for ESPN Stats & Information.