David Ortiz reportedly is looking for a three-year contract from either the Red Sox or a new team willing to give it to him. Contracts that guarantee the ages Ortiz is looking to have locked up (36, 37, and 38) are rare, especially for a DH. Frank Thomas hit .252/.361/.472 as a 34-year-old, and received a two-year deal from the White Sox (then he posted a 149 OPS+ over the next two years). Jim Thome signed a six-year deal before the 2003 season, but only his age-36 and 37 seasons were covered by the contract -- his age-38 campaign was an option year, and therefore not guaranteed.
Looking a little further back, Edgar Martinez's contract expired after his age-37 season, prompting the Mariners to sign him to a one-year deal with an option for the next two seasons. Reggie Jackson signed a five-year deal with the Angels before the 1982 season, after his age-35 campaign. But those were the early days of free agency, too. There wasn't anything to compare many of these contracts to, and some ridiculous (for the time) dollars and years were thrown around in the name of bringing home a shiny new bauble. Jackson was also a part-time DH who played more outfield than anything, so his deal doesn't quite fit the bill.
What you often find with designated hitters at this late stage of their career are one-year deals, like the ones Ortiz's peers, Vladimir Guerrero and Hideki Matsui, signed before the 2011 campaign. Ortiz essentially inked one as well, thanks to that one-year option, a move that was an overpay for a year in the sense of how the market was going. For Ortiz, though, it fit, as the extra monetary padding helped quiet the multi-year deal discussion. Temporarily, anyway.
Ortiz had a fantastic 2011 campaign, one of the most productive ever for a 35-year-old (or older) designated hitter, so it's no wonder he is now speaking up about multiple years, market and history be damned:
Notice a theme, here? These names don't appear more than once for the most part. Thome has a pair of seasons, and Edgar Martinez has four -- yes, four of the top 10 35-and-up DH seasons are courtesy of Edgar. Other than that, it's all one offs. Jason Giambi has hit .236/.362/.458 since his one year on this list (113 OPS+). Frank Robinson, except for one more decent season, was a part-timer following his 1973. McRae had a 114 OPS+ after his age-36 season, sticking around for five more seasons, but, like Giambi, saw his playing time diminish.
As you can see, using the "But his age-35 season was amazing!" argument only goes so far, as the rest of these guys were pretty good at hitting a baseball, too. The main concern with whoever signs Ortiz is what you're getting. Is he going to turn out to be expensive and less useful with time? Will he end up as a part-timer, unable to face left-handers perhaps, or with a bat that slows and makes mistakes his only avenue for success? Or will he be that rarity, an Edgar Martinez, who just keeps on hitting for years?
We don't know. The Red Sox don't, either. And neither do any of the teams courting Ortiz. They might have an idea, sure -- so do we -- but they don't know.
Risk is what makes three years to Ortiz problematic. The reward is there for a team brave enough, misguided enough, or full of enough depth to make it work. But the investment of years and dollars that Ortiz expects is going to make things difficult for most clubs. They might be more afraid of locking up the next Giambi, McRae, or Frank Robinson than they are excited at the prospect of the next Edgar Martinez.
That makes Ortiz leaving Boston even more unlikely, as another team has to do something somewhat nuts to pull him away from the Sox. Ortiz will likely end up with a heavily-compensated one-year deal, or a two-year contract. The risk with Ortiz goes down the fewer years are committed to him, and given his age and the history of players at his position, it's hard to imagine anyone absorbing three years of risk.