Mets shortstop Jose Reyes is primed for a payday as he prepares to enter free agency on the heels of a strong season at a position where offense is scarce. Though injuries have limited him to 101 games, Reyes’ bat has been the best of any shortstop’s on a rate basis, producing a .315 True Average (TAv) that is tops at the position and a .336 average that leads the National League. In terms of overall value, the 28-year-old Dominican is tied for first with Troy Tulowitzki at 4.5 Wins Above Replacement (WARP).

Reyes will become available to the highest bidder in an offseason that features few attractive options for suitors in search of a shortstop. In the wake of recent extensions granted to J.J. Hardy and Yunel Escobar, the market will largely be restricted to past-their-prime veterans on their last legs like Orlando Cabrera and the recently-released Miguel Tejada, as well as defensive specialists like Cesar Izturis, John McDonald, and Jack Wilson. Beyond Reyes, only Jimmy Rollins and Rafael Furcal (whose $12 million club option is unlikely to be exercised) offer any real offensive upside, and Reyes is the lone member of that trio on the youthful side of 30.

That perfect storm of positional scarcity should have Reyes and his agent Peter Greenberg salivating, but how smart an investment is the lifetime Met, and how long should teams be looking to commit when they start approaching him with multi-year packages? All long-term contracts are fraught with risk, and while position players are generally safer bets than pitchers, Reyes represents more of an actuarial puzzle than most. His 2011 season is a microcosm of his major-league career: periods of dynamic and productive play, interspersed with extended absences due to injury.

Reyes returned from his latest stint on the disabled list on Monday, his second such forced absence this season and seventh overall (including two extended stays on the 60-day). Altogether, Reyes has spent over 350 days unavailable due to injury since his first full season in 2004; since players often become more susceptible to injury with advancing age, his next team could well be in for more of the same. Worse still, his health trouble has often been concentrated in his hamstrings, which suggests a chronic problem that repeated rest and rehabilitation have been unable to solve.

Even if Reyes isn’t hurt, his next team (or his current one, should he remain in New York) will likely have to rest him regularly just to minimize the risk of losing him for longer periods, a protective measure that Mets manager Terry Collins has already implemented.  Baseball Prospectus’ proprietary injury projection system, CHIPPER, paints Reyes as an undependable player in the short term, giving him a greater-than-85-percent chance of losing at least 30 days to injury in 2012. CHIPPER doesn’t project further into the future, but it’s unlikely that Reyes will be a safer bet at 35 than he is at 28.

BP’s performance projection system, PECOTA, generates comparables in order to develop custom aging curves for each player. By examining the list of players deemed most similar to Reyes at the same age, we can get some sense of what might lie in store for him. Reyes’ top two PECOTA comparables are also members of the upcoming free-agent class: Rollins and Furcal. Rollins enjoyed a career year in his age-28 season—the campaign Reyes is about to complete—but his subsequent work has been a mixed bag. Of the four seasons since, one was excellent, another was above-average, a third was a disaster both at the plate and in the field, and a fourth was moderately productive but shortened by a lingering calf strain.

Furcal’s early 30s have told a similar tale. The back, not the hamstring, has been Furcal’s least cooperative part, but he’s also tended to be productive when healthy. He was limited to 36 games in 2008 and 97 last season; this year, he’s succumbed to both injuries and ineffectiveness, making two trips to the DL and putting forth a replacement-level performance when he has been on the field. Reyes’ top-10 comparables also include Barry Larkin and Carlos Beltran, two more oft-injured sometime stars, as well as Roberto Alomar, who followed a career year in 2001 by falling off a cliff at age 34, and Chuck Knoblauch, who was essentially finished after age 32. The company Reyes keeps in PECOTA’s similarity index hints at his top-flight talent, but it can’t be reassuring to any team considering an investment in his future.   

On the plus side, Tom Tango’s research has revealed that players who derive a high percentage of their value from speed tend to age more gracefully than the population of players as a whole. Tango discovered that a speedy player like Reyes in the age-29-31 bracket can expect to lose more than four wins less over the life of a seven-year contract than a player who’s less fleet of foot. It’s not clear if this is because speed itself is more resistant to the effects of age or because speedy players tend to be more athletic, better-conditioned, and more capable of compensating in other areas as their physical gifts diminish, but regardless of the reason, speed works in Reyes’ favor when it comes to long-term deals.

Given his age and the long-term contracts awarded last winter, it’s likely that Reyes will be looking for a pact in the neighborhood of seven years, a length that could allow him enough time to sign an additional multi-year deal before calling it a career. The list of position players recently awarded contracts of at least seven years in length includes a number of regrettable deals—come on down, Alfonso Soriano, Alex Rios, and Vernon Wells—as well as a few more that have gotten off to disappointing starts—better luck in 2012, Joe Mauer, Carl Crawford, and Jayson Werth—with extensions for Albert Pujols and Chase Utley probably representing the most encouraging precedents.

Reyes has answered some questions this season, recovering all of the on-base percentage points he surrendered in 2010 (and then some), but he’s made others only more pressing, returning to the DL twice with a painfully familiar complaint. He’s very likely in line for a nine-figure payout despite the missed time, so there is little doubt that he’ll be quite comfortable regardless of how the offseason plays out, but the more years are tacked on to the end of his next deal, the more likely it is that the team that wins this winter’s sweepstakes will lament its commitment to a player who so often comes up lame.

Most long-term deals are bad bets, since the "Winner's Curse" usually ensures that the team that emerges from a free-agent bidding war victorious has to overpay for the privilege. Clubs are often willing to take a bath at the back end of a deal in exchange for a few productive seasons early on, but unless those glory years lead to a championship (and sometimes even then), the latter portions of long-term pacts often lead to buyer's remorse. What's more, Reyes' fragility suggests that his decline phase could be more precipitous than most, threatening to hamstring—in his case, quite literally—his club's efforts to compete and making a lengthy commitment even more ill-advised. With so few marquee shortstops available, the urge to throw caution to the winds and add one of the position's few standouts will be strong, but Reyes' track record doesn't justify a Crawford-sized contract. If the negotiations take a turn in that direction, the wise GM won't wait to bow out.

A version of this story originally appeared on ESPN Insider Insider.