The Cubs and Toronto first talked trade in early October. Among the many names that were mentioned was star pitcher Roy Halladay. Halladay, going into the last year of his contract before becoming a free agent, will be shopped extensively by the Blue Jays during this offseason. The one caveat is that Halladay has a complete no-trade clause, which allows him to stop any type of deal unless he first approves.
Among the names that the Cubs and Blue Jays talked about was Vernon Wells in the original scuttlebutt that got out about a possible Milton Bradley-for-Wells deal. Toronto also talked to the Cubs about Lyle Overbay; another contract the Blue Jays would like to rid themselves of. Actually, Toronto has talked to many teams about the big contracts they have committed to Wells, Overbay and Halladay. Toronto is trying to go young and free themselves of the heavy payroll load that they are committed to at this point.
As far as Halladay and the Cubs, it doesn't look good for the North Siders to be able to come up with the kind of money it would take to take on his contract. The most feasible situation would be to trade Carlos Zambrano and at least one of the top young prospects in the system like Starlin Castro, or Josh Vitters, in any deal that would make sense for both sides. The problem with that type of trade is two-fold: One, Zambrano has a full no-trade clause, and two, trading the team's top future prospect at shortstop by moving Castro would be counter-productive to what the team is looking forward to in years to come.
Halladay will most likely be traded in the offseason, but trading him to the Cubs is a real long shot. First and foremost, general manager Jim Hendry has to move Milton Bradley's contract. The most logical team still remains to be the Tampa Rays, who are hoping to include Pat Burrell in the deal. For the Cubs, that would mean that they would have to complete that trade, eat some money on Bradley's contract, and then trade Burrell.
The Cubs already have a long-term commitment (five years) to a left fielder who is below average defensively and strikes out too much. Therefore, it will be imperative for Hendry to move Burrell's contract before the season begins.