Ryan Dempster rejected a two-year, $25 million contract from the Red Sox just this past weekend. Dempster is looking for three years, and $13 million per season, and would also like to pitch in the National League for a team that has spring training in Arizona. Given that, it's not a shock to see him turn down the Red Sox considering their offer fulfilled exactly zero of those requirements.
Dempster's laundry list of wants is apparently flexible, though, as, according to Ken Rosenthal, the two sides are in serious discussions about a contract still, even after this recent rejection. There's no word on what those talks are, or what Boston (or Dempster) are giving in on in order to make it work. But just talking is news on its own, considering things seemed a bit dead just a few days ago.
The right-handed Dempster has had issues with lefties over his career, but Fenway Park is the park to stop that. And, considering how friendly Wrigley is to left-handed hitters, Dempster didn't do half bad during his nine seasons there, amassing a 114 ERA+ with success as both a reliever and a starter, while limiting the opposition to a .129 Isolated Power at Wrigley. He's durable, has averaged 199 innings in the five seasons since returning to the rotation, and while in his mid-30s, should still have plenty left in the tank. Just maybe close your eyes if he has to pitch in Yankee Stadium against a bunch of lefties.
Dempster isn't a bad option, but it all really depends on the terms of the contract. As with any of the options out there, the performance of the rotation members already in place means a whole lot: Dempster is great as an additional piece, but not as the lead arm.