In his latest column for Sports Illustrated, Jon Heyman suggested that free agent-to-be Cliff Lee might be preparing to ask for something similar to the seven-year, $161 million deal that his friend, CC Sabathia got two off-seasons ago.

Via Sports Illustrated:

Before Halladay took a $60-million, three-year extension with Philly, Lee turned down a similar offer, believed to be for three years and somewhere in the mid-$50-millions from Philadelphia, who eventually traded him to Seattle. Word was, he was thinking about more than double that, maybe something close to Johan Santana‘s $138-million, six-year Mets contract.

Now, rumor has it that Lee might seek three times what Philly offered. In other words, Lee might try to match his old Indians teammate CC Sabathia’s deal, which is for seven years and $161 million. “Why not?” one club executive said. “He’s as good as Sabathia.”

There are some pretty big differences, though, between Lee and Sabathia. The biggest is probably the fact that CC was 28 when he signed his deal with the Yankees and Lee is already 32-years-old.

Those four years are pretty huge in this case. The Yankees had no problem giving a 28-year-old a seven-year deal, at the end of which he will be 35. A 32-year-old will be 39 at the end of his seven-year deal.

Also, the fact that Sabathia is viewed as a guy who can handle a ton of innings with relatively few injuries. Lee, on the other hand, has already dealt with a few injuries during his career and has been dealing with back problems as recently as a few weeks ago.

The thing that Lee does have going for him is that he is in much better shape than Sabathia, and as Heyman points out, relies on velocity much less than Sabathia does.

Also in Lee’s favor, the Yankees are desperate. They really want him. They want him so badly, they were willing to deal their top prospect, Jesus Montero, for him despite the fact that he’s a catcher, as is the 39-year-old Jorge Posada.

Realistically, I could see the Yankees offering him a six-year deal at anywhere from $120-140 million. The bottom line, though, is that Lee is a unique player to hit the market; another pitcher of his caliber will not be available soon. The Yankees will offer them whatever they have to bring him to the Bronx.

My guess is that he ends up with a five-year, $120 million deal. Unless the Rangers are willing to spend that much, all bets are off.

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