Anthony McCarron writes that the list of pitchers with $100 million contracts is neither long nor encouraging:

Long-term contracts for pitchers are generally considered risky by baseball executives, but when deals reach the $100 million mark, teams flirt with doom. In the brief history of $100 million contracts for pitchers - there have been only four, including Kevin Brown who signed a seven-year, $105 million deal with the Dodgers before the 1999 season - every pitcher except Johan Santana last season has been plagued by injuries, ineffectiveness or both.
Still, CC Sabathia figures to make much more than $100 million this winter, and several teams have determined he's worth the gamble of a mega-deal. The Yankees have already offered him $140 million over six years, and some in the game believe the Angels will come close to that. The Brewers have a five-year, $100 million offer on the table, too.
While Sabathia has proven he's a terrific, durable pitcher, there are plentiful cautionary tales for the Yankees, Brewers and Angels to consider. None of the four previous $100 million pitchers - Brown, Santana, Barry Zito and Mike Hampton - has pitched in the playoffs for the team he signed with. In fact, none of the teams that have signed a pitcher to a nine-figure deal has made the playoffs while that pitcher has been on their roster.
"The dangers in these kinds of deals are tremendous," said a baseball executive who spoke on condition of anonymity. "How old is the pitcher? What is his history of injury? Based on his age, how fast will his performance decline, because most pitchers, as they get older, they lose their velocity and have to become more of a pitcher and mix it up, change.

How old is the pitcher? He's 28.

What is his history of injury? He has almost none. In 2005, Sabathia missed the first two weeks of the season with a strained oblique muscle. In 2006, he missed most of April with a similar injury. Since then, he hasn't missed a start. In his eight-year career, he's averaged 32 starts per season; he's one of only eight major leaguers to start more than 250 games over that span.

Based on his age, how fast will his performance decline? Well, again, he's only 28

Nobody's a sure thing, and that goes double for pitchers. But other than the potential contract, I don't see that Sabathia's got much in common with Kevin Brown, Barry Zito, or Mike Hampton. Brown had been up and down, durability-wise, and was well into his 30s when the Dodgers signed him (and it should be said that he did pitch brilliantly for two years). Zito was a disaster waiting to happen, his performance obviously slipping long before the Giants signed him. And Hampton was a very good pitcher who was thrown into an extreme environment.

Essentially, all three of those deals were festooned with red flags from Day 1, and I'll bet that if you take a few minutes and look, you can find a bunch of pointy-headed sabermetricians who cautioned against them immediately.

Johan Santana, though? Not so much. Aside from the uptick in homers allowed in 2007, there simply wasn't anything about Santana not to like (and the homers ticked back down in 2008). I'm not convinced that he'll ever again be the pitcher he was in Minnesota -- his strikeouts ticked down this year -- but Santana is the sort of pitcher a team like the Mets has to sign.

The same goes for Sabathia. He's relatively young, and yet he hasn't been particularly overworked; in his first six seasons, he threw more than 200 innings just once. His track record is obviously impeccable, as he won the Cy Young Award in 2007 and was probably the best pitcher in the major leagues in 2008.

If I were considering signing Sabathia, there's really just one thing I would worry about: He's the most massive great pitcher we've ever seen. Sabathia's listed weight is now 290 pounds. Maybe it's because of rank political correctness, but Sabathia's build seems to me like the elephant in the room that everyone's ignoring.

There isn't another pitcher like him, and never has been. What happens to 290-pound pitchers as they move into their late 20s and into their early 30s? If it were me trying to sign Sabathia, that's the single unanswerable question I would ask the smartest people around me to answer.