There is no doubt that if (and 'when' in many peoples opinions) that Jays are without a shot at the playoffs that Alex Anthopoulos would be looking to move certain players in the right deal. Contenders are looking to boost their chances to go deeper into the playoffs while taking advantage of their trading partner. The Jays would surely look at any deal that would give them a piece moving forward.
One thing that many people always wanted from former G.M. J.P. Ricciardi was an admission that the team was not in contention. Often, it seemed, he was in denial and refused to move pieces before the trade deadline. For example, when A.J. Burnett was pitching well in what would be his final season for the club, Ricciardi was unable to make a move that may have helped the club. He may not have had a viable offer (and he could not have foreseen the Yankees signing two higher rated free agents), but there was little doubt that he was going to opt-out of his deal and leave for another long-term contract. If there was a deal that could have brought back prospects worth more than the picks that they would have received, then a deal should have been made. That all sounds familiar to the Roy Halladay situation that was just endured.
This year, the Jays will be a team which will be called early and often. As a rookie general manager, Anthopoulos will probably receive some low-ball offers, but he is smart enough to know the value of his assets.
A few Jays that contending teams could be looking at:
1B Lyle Overbay
With an expiring contract at $7 million and hot shot prospect Brett Wallace hot on his heels, Overbay will be moved if there is any deal that would bring back proper compensation. Not only would the acquiring club receive a good defensive first baseman (and righty masher), but they would pick up draft pick compensation at seasons end. If the player package heading the Jays way cannot exceed the compensatory picks then the deal may as well not be completed. However, if Wallace is able to surprise in spring and get off to a good start in Las Vegas, he may force the Jays hand in making a deal.
RP Scott Downs & Jason Frasor
Both releivers would, assumably, slide right into a contending teams 7th or 8th inning role perfectly. Both pitchers may be forced into a closing role here in Toronto, but the team getting them would probably have someone already in place as the closer. Teams would probably be hesitant in giving up any top prospects, but many are prone to give up more than normal when they are in a playoff push. Another guy who may fall into this group, but has the ability to start too is Brian Tallet.
SS Alex Gonzalez
As I have said before, many clubs are in search of stop-gap shortstops who are reliable with the glove and won't kill you with their bats. Gonzalez was a victim of the trade deadline last year when he was shipped from the Reds to the Red Sox. He may be in a similar situation this year if he has a strong enough year to gather some interest.
Something that always bothers me is when contending teams are looking to acquire players, but are reluctant to give up unproven prospects for legitimate major-league players. All teams should keep an eye towards the future, but if you are building up your minor-league system for the major-league playoffs, then why wouldn't you be willing to ship them out for someone who is going to help you in the present time. A perfect example from this offseason is the Philadelphia Phillies and their refusal to keep Cliff Lee. To pair him up with Halladay and Cole Hamels would have created a formidable playoff rotation. They were willing to give up a proven pitcher for prospects who are highly-regarded, but not sure things.