In the wake of Tim Lincecum's recent re-up with the Giants, I took a look back (using MLBTR's Extension Tracker) to see if there were any comparable starting pitching extensions agreed upon during post-season play. There were: each of the last four offseasons has seen one (and only one) rotation member sign a new deal with his club during the month of October. Though the Yankees' massive extension of C.C. Sabathia is not really comparable, the other two deals are. Rather than just asking for an up-or-down vote on the Lincecum deal, I thought it might be more interesting to approach the question in a bit of historical context.
In 2010, the Dodgers decided to hand Ted Lilly a three-year, $33MM deal. In doing so, Los Angeles kept Lilly from reaching the market as a probable Type-A free agent, which might have suppressed his value and would have allowed the club to recoup two draft picks if he signed elsewhere. And in 2012, the White Sox gave Jake Peavy a two-year, $29MM deal, including a club option for 2015 that could have vested (but will not) to become a player option. In so doing, Chicago also agreed to pay Peavy a deferred $4MM buyout on the $22MM option the club already held on him. Of course, the Sox could also have decided to make Peavy a qualifying offer -- at essentially the same average annual value they promised him for two years -- to keep his price down in free agency and deliver a first-round draft choice if he went elsewhere.
Of course, we now know how those two deals turned out for the clubs signing them. Lilly was solid, if unspectacular, in 2011, putting up a 3.97 ERA in 192 2/3 innings. He was off to a nice start over his first 48 1/3 innings in 2012 when he was knocked out of commission by a shoulder injury. He was ineffective in just 23 big league innings this season, and ultimately returned less than 2 WAR over the life of the contract. Meanwhile, Peavy fell well short of his outstanding 2012 season in the first year of his new deal, ultimately throwing 144 2/3 innings of 4.17 ERA baseball, good for 2.4 fWAR and 1.5 rWAR. He was reasonably effective, but hardly dominant, for a sputtering White Sox squad before suffering a broken rib that endangered his status as a trade deadline target. Nevertheless, his pre-deadline return enabled the South Siders to flip Peavy to the Red Sox and return prospect Avisail Garcia (and others), while shedding the remainder of his salary.
Much as with Lilly and Peavy, Lincecum signed his new contract before his present club could make him a qualifying offer that would have limited his free agent prospects. Indeed, the San Francisco front office sought to justify Lincecum's price tag in part by noting that he would have received about the same amount had he accepted consecutive qualifying offers this year and next.
Ultimately, the Lilly and Peavy deals show two possible outcomes for Lincecum's own contract. Though Lincecum is somewhat younger than the other two, he has nearly as many innings on his arm as they did. Injury or ineffectiveness could render the deal a major waste of resources. Or the Freak could pitch well enough for other teams to view the remainder of his contract as a valuable commodity. (Even if his no-trade clause would present a significant barrier to an actual deal.) Which outcome seems more likely at this point?