Joba Chamberlain for Roy Halladay: Would You Pull the Trigger?

There are nights when it all must become too much for J.P. Ricciardi to bear.

Restless evenings where the Blue Jays general manager stares at the ceiling of his plush Toronto condominium and instead of counting sheep, only sees Jacoby Ellsbury triples, CC Sabathia shutouts, and Carlos Pena walk-offs.

It's these visions that can drive a man to insanity...or to trade Roy Halladay.

The Blue Jays' fast start and subsequent "Hey, these guys are dangerous because they believe in themselves!" stories are long gone, replaced by the bitter reality that Toronto plays in a division that arguably houses the three best teams in baseball.

While mid-budget teams like the Blue Jays can succeed (the Rays being the most obvious example), Toronto's roster and farm system simply don't stack up as presently constituted. A facelift is necessary to compete in the treacherous AL East.

Halladay is 10-2 this season and perhaps the most respected starter in baseball. He has become the hottest midseason trade candidate of the decade. If Ricciardi plays this right, he can retool the franchise for years to come.

The team that lands Halladay, meanwhile, becomes an instant postseason favorite.

The popular thinking around baseball is that the Phillies are the front runners for Halladay, and that the Yankees will be nothing more than mischief-makers in the process.

But just for fun, let's imagine the Yankees managed to acquire Halladay. A rotation led by Sabathia, Halladay, and A.J. Burnett heading into the postseason? That's downright scary.

Halladay's price tag would obviously be huge, and there's no way you'd be able to acquire him without it hurting...a lot.

Like, Joba Chamberlain a lot.

The Yankees famously passed on Johan Santana two years ago, unwilling to deal their best prospects for the ace left-hander. Even with Phil Hughes' emergence as a bullpen weapon this season, you have to wonder if it's a decision that still eats at Brian Cashman.

Halladay, in that sense, could be a chance at a mulligan for the Yankees GM, and Chamberlain is the blue-chip name that could get a deal done.

Joba has certainly given the Yankees (and their fans) fits this season, but he remains a tremendously promising talent. The organization still regards Chamberlain as a future ace in his own right. Just how strongly they believe that would dictate whether a deal could ever happen.

Let me close by throwing a scenario at you.

Ricciardi, having not slept in four weeks, calls you at 4:00 a.m. tomorrow and dejectedly mutters, "Halladay for Chamberlain, Frankie Cervelli, and David Robertson. Take it or leave it."

I don't know about you, but I've got Halladay starting Game One of the ALCS at Fenway Park.

What's your move?

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