Should Ghost of Carl Crawford Still Haunt Theo Epstein?

Both Halloween and the start of free agency are upon us, which makes it a great time to revisit the most famous ghost in Theo Epstein’s closet: Carl Crawford. Easily considered the future Hall of Fame exec’s worst free-agent signing, it’s worth reviewing for any lessons that may still haunt Epstein this offseason.

As a refresher, Crawford entered free agency after the 2010 season. He had a two-year combined WAR of 12.0 and was the big “it” position player in that class. He had it all. Entering his age-29 season, he ranked in the AL’s top 5 in offensive WAR, runs scored, stolen bases, and Bill James’ power/speed mix rating. His batting average (.307) was also top 10, and he had won a Gold Glove.

Using Boston’s big payroll and a desire to beat the Yankees at all costs, Epstein signed Crawford to a seven-year, $142 million contract. That’s one year shorter than Jason Heyward’s contract, but when inflated to today’s dollars, the annual average value (AAV) of Crawford’s deal was actually $2 million more ($25M to $23M).

Epstein certainly won that offseason over the Yankees, who saw lefty starter Cliff Lee spurn a $138 million offer. But then Crawford flopped in every way possible. In 2011, he produced a paltry 0.3 WAR and would average just 0.7 WAR over the next five years.

One season later, Epstein’s successor, Ben Cherington, traded the bad contracts of both Crawford and Josh Beckett to the Dodgers. The cost included shipping a still-prime Adrian Gonzalez, but it helped clear Boston¹s payroll decks. Cherington then retooled with a mess of smaller signings: Mike Napoli (3 years, $39M), Shane Victorino (3/$39M), Stephen Drew (1/$9.5M), Jonny Gomes (2/$10M) and David Ross (2/$6.2M). All would be key to the the Red Sox’ 2013 World Series victory.

One narrative about the Crawford signing has it that it was forced on Epstein as part of his power struggle with Red Sox team President Larry Lucchino. This is not true, as Epstein himself dispelled. It also runs counter to Epstein’s eagerness to flex big-market power and go after the biggest free agents.

So with the mega-contract decisions of Bryce Harper and Manny Machado looming, should Epstein mind the Crawford ghost? Might Harper’s injury history and less than stellar record against elite playoff pitching serve as a ill omen? Or should Epstein be scared off by Machado’s lack of hustle during the Dodgers’ unsuccessful title run and other character flaws?

The Cubs organization could also consider the Cherington model of going with a smaller, more precise passel of free agent signings and trades to fill in around a quality core.

The answer is not easy. As Cubs president, Epstein’s bids for Jon Lester and Ben Zobrist certainly paid off. But Heyward has been a mixed bag and Yu Darvish gets an incomplete so far. And as the Tyler Chatwood signing reminds, even more modest contracts (3/$38M) can slide off the tracks.

So in keeping with today’s chant of “trick or treat, smell my feet,” will this year’s signings lead to a bag of goodies or leave a stank on the organization for years to come? That is the risk every free agent season. Who knows if today’s great signing today remains prized tomorrow or if he pulls off his costume to reveal the ghost of Carl Crawford.