CC Sabathia's timing was perfect. Both for when he became a free agent and when he finally agreed to terms with the Yankees. Barry Zito elevated the bar for pitchers with his $126M contract he signed with the Giants after the 2006 season while Johan Santana moved out of the way a winter ago after he was dealt to the Mets and subsequently signed a $137.5M extension. The Yankees were in the mix for Santana but chose not to part ways with their prospects although it can, of course, be argued that the two picks they will be forced to relinquish for Sabathia will someday be every bit as valuable. In hindsight, if the Yankees would have made the trade for Santana last winter, they probably don't miss the playoffs in 2008, have a zero sum on the prospects lost versus the draft picks, and would be one less year invested in Santana at an identical annual cost than they will be with Sabathia, which can, of course, cut both ways. For Sabathia, he didn't have a peer among pitchers in the free agent market. Derek Lowe can't match Sabathia's age. Ben Sheets can't match Sabathia's durability. A.J. Burnett can't match Sabathia's overall makeup. Since 2006, Sabathia and Santana have been the best two pitchers in the game, but Santana has been slightly better with a 2.87 ERA compared to Sabathia's 3.03. Santana also has a better strikeout rate, quality start percentage and WHIP. They are both among the very best in all of these categories, but Santana edges Sabathia in all of them. Sabathia also hasn't been able to be an effective postseason starter, giving up 22 earned runs over 25 innings in five separate starts. There is no denying that he can pitch in big games, however, as evidenced with how well he pitched down the stretch for the Brewers on short rest. He has averaged almost 32 starts per season since 2001 with his low only being 28 back in 2006. He is extremely durable and has the kind of presence in the clubhouse that any pitching coach would want to build a rotation around. This kind of infectious character Sabathia innately possesses is a very close second (after pure talent of course) for what makes this signing so undeniably valuable for the Yankees. Sabathia is much more Paul O'Neill than he is Kevin Brown or Randy Johnson. His presence in the dugout and clubhouse on the every four days he's not pitching will also be incredibly important to a Yankee team that is not as teflon as it was in the late 90s. Sabathia is unquestionably a nine-figure contract kind of player, but in terms of a return it is impossible to expect the 1.65 ERA he had in Milwaukee and also difficult to count on a level of performance that truly matches Johan across the board although he won't be far off. For a team like the Giants or Brewers that also wanted Sabathia, they would need a 1.65 ERA over the six or seven years of the deal for nine-figures to be considered a sound investment. But for the Yankees, the stability of 200+ annual innings with an ERA in the 3.00 neighborhood and the possibility of brilliance and dominance in October is more than enough to justify the price tag. What was perhaps most impressive about this process was the almost obscene level of patience Sabathia demonstrated in leaving the Yankees' $140M offer on the table for nearly a month (Brian Cashman delivered that proposal on November 15th). Sabathia and his camp did not have any leaks of what he was trying to accomplish in waiting other than maturely weigh his options. He comes out of his free agency as admired and genuinely congratulated for being $160M richer (and with $20M more than initially offered) than I think anyone else is capable of and that was because he made family his priority despite still taking the biggest offer. For the Yankees, they get their guy and do not have any lasting chinks in their armor because of the wait. I'm sure it was almost fun for Cashman and company in some way and this, their theme song to their offseason as they move a block north to their new stadium, sounds a little more dramatic. Not counting the Nick Swisher trade or the unorthodox way of how they re-signed Damaso Marte, signing CC Sabathia to the richest contract ever for a pitcher is an excellent first move to return to the playoffs. Grade for Yankees: A- Updated: Sabathia's contract includes an opt-out clause after the third year, which knocks the grade down for the Yankees to a B-. The only way Sabathia will not opt out is if he under performs the contract or gets injured and if the financial climate is healthy and he continues to be a perennial Cy Young contender, the Yankees will have to negotiate a new deal that would probably take him to the doorstep of 40. Grade for Sabathia: A++