Reason #1 - Because he can't hang in the AL
With all of the requisite caveats about small sample sizes, let us just note that Dempster's career ERAs versus the Yankees (6.88) and the Red Sox (7.13) don't exactly inspire us. Dempster also got smoked for eight runs in 2.1 innings against the White Sox on June 27 last year. All that glove twitching and junkballing might work against the Houstons and Cincys of the world, but we're guessing that once the boy is put into a man's league, his results may vary.
Reason #2 - Because his arm is due to fall off sometime in early 2009
After four years in the bullpen and three years as a closer, Dempster pitched 206.2 innings last year. That's a year-over-year increase of 140 innings from 2007 to 2008. Knowing that, is there anyone who would really want to hitch their wagon to him for four years at $50 million?
Reason #3 - Because he's gonna be too damn expensive
As mentioned just above, the Cubs' "hometown discount" offer was apparently $50 million over four years (according to Paul Sullivan of the Tribune.) That's a lot of money for a guy who will likely never put up a season as good as last year. A contract like that is fine for the Cubs, but if it were to go wrong for the Jays, it could hinder the team's ability to maneuver and adjust for the next few years.
Reason #4 - Because we remember Corey Koskie
Sometimes, those stories of bringing home good Canadian boys to play for their "home team" just don't pan out. We've got a feeling that Dempster, the hometown boy who grew up 4,422 kilometres away from the SkyDome, might get a king's welcome to Toronto from the rather parochial sports press in the Great White North. But we doubt that warm and fuzzies will do much for the Jays in the win column.
Reason #5 - Because that Harry Caray impression won't play here
Sure, we get that Dempster's a hoot. A real cut up. But we've heard his impression of Harry Caray one time too many, and we've always felt like his impression is really an impression of Will Ferrell's impression. He might leave Jamie Campbell in stitches, but we'll take a pass on his comedy stylings.