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A familiar waiting game for Stephen Drew, Red Sox

01.31.14 at 8:15 am ET
By
Stephen Drew (AP)

Stephen Drew remains unsigned as the start of spring training approaches. (AP)

It may seem as if it’s taken forever for Stephen Drew‘s fate to be determined, with his unresolved free agent status for the 2014 season becoming ever more glaring on the doorstep of February. Yet while it would be natural to assume that the uncertainty would be grating on Drew, it’s worth noting that this is not his first such rodeo. Indeed, the shortstop has pushed the limits of a signing period much further than the 93 days that have transpired since the conclusion of the World Series.

In 2004, Drew was taken by the Diamondbacks with the No. 15 overall pick in the draft — a spot to which he’d slipped based on signability concerns, despite the fact that many viewed him as the top position player in that draft. Those signability concerns proved well founded when Drew struggled to find common ground with Arizona.

Though he initially believed that he was close to reaching an agreement with Arizona under then-CEO Jerry Colangelo, Colangelo was forced to resign in the middle of those negotiations, and Arizona subsequently expressed reluctance to exceed its recommended slot value while in a leadership transition.

The experience could have proved unsettling. It wasn’t. Instead, Drew barely blinked.

His older brother, J.D., had endured his own complex negotiations after being drafted by the Phillies with the second overall pick of the 1997 draft. The outfielder ended up playing in an independent league, returning to the draft in 1998 and getting taken by the Cardinals with the fifth pick — signing for millions more than what Philadelphia had offered.

Familiar with that history, Stephen was comfortable waiting … and waiting … and waiting for the right deal from Arizona. He signed with the Camden Riversharks of the independent Atlantic League in April 2005 while preparing for the possibility of re-entering the draft in 2005.

“They had a lot of things going on in the organization. They got a new owner so we had to work out a whole new contract. But, with that said, I knew I could play in an independent league, stay ready and stay in shape,” Drew recalled last year. “If I didn’t get inked by them, I’d go back, because I was proving myself in a wood bat league. I was doing well and still was playing. So I think that took care of itself.”

Drew ended up playing 19 games with the Riversharks, hitting .427 with a .484 OBP and .744 slugging mark, a performance that validated the Diamondbacks’ assessment of him. Finally, he ended up reaching an agreement at the end of May — 51 weeks after he’d been drafted — on a four-year deal that was worth a guaranteed $5.5 million with incentives that could push it up to $7.5 million.

So, Drew has a history of patience when it comes to his willingness to search for the right deal. That said, the Red Sox also have a history of waiting out a Scott Boras client whose market is limited.

After the 2008 season, the Red Sox offered catcher Jason Varitek — like Drew, a player represented by Boras — salary arbitration in order to ensure that, if he signed elsewhere, they would receive a pair of compensatory draft picks. With Varitek coming off a career-worst year, his market was chilled when teams balked at the idea of paying market value for him and sacrificing a draft pick in order to do so. As such, the catcher remained in limbo until Jan. 30 before finally reaching a two-year, $8 million agreement with the Sox — making less in two years than he would have received in one year had he accepted the team’s offer of arbitration.

Now, Drew appears to be in a similar box as a result of the Sox’ decision to extend a qualifying offer (one year, $14.1 million) to the shortstop after the 2013 season. With teams appearing reluctant to sacrifice a draft pick, it remains to be seen if a team will offer the shortstop a better deal than the one he declined from the Sox right after the season.

Thus, the waiting. For some, that suspended state would be a mind-bending exercise in uncertainty. For Drew, it’s a familiar undertaking.

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