The time is slowly coming where the Blue Jays roster will start to change as free agency gets going and the Winter Meetings approach. While much of the focus is on which players the team should add to make the team stronger, there's a flip side to the equation which is what players the team needs to part with the most. A range of factors including previous play, contract situations, and positional logjams affect which players the Alex Anthopoulos and company will be trying to rid themselves of this offseason. Obviously the massive contracts the Blue Jays are stuck with from the Marlins trade make them pretty difficult to move, but there's a lot of GM's in the league that make questionable decisions so nothing is impossible.
The two most expensive contracts for the Blue Jays in 2015 are held by Jose Reyes ($22 million) and Mark Buehrle ($20 million), products of the Marlins trade, who have provided solid play during their time in Toronto but not enough to warrant their massive salaries. Buehrle had his best season in quite some time but if you consider a win costing somewhere between $6 and $7 million, then his 3.5 fWAR only just surpassed his $19 million salary. It's unclear how many more years Mark has left in his arm, but to hope that he repeats his solid 2014 campaign next season is a pretty big risk that could actually be a key factor in how well the 2015 year goes for the whole team. With free agency looming after next season, clearing Buehrle's $20 million from the books would go a long way to getting some financial flexibility this offseason. This financial flexibility is something the Blue Jays are currently lacking and sacrificing a solid starting pitcher may be worth the risk to open up a lot of money for other improvements.
Reyes had a 3+ WAR year as well, but his $22 million per season salary over the next three seasons is beginning to look like a nearly impossible contract to get rid of as he begins to enter his mid-30's. His defence at short is starting to look rather average and $66 million freed up in the future would allow the team to find a suitable replacement for less money while adding the flexibility to make other upgrades as well.
Another aging starter pitcher who earned his contract this season but might put the team in a better situation if he was shipped off is R.A. Dickey. The likeable knuckleballer is about to turn 40 and has another $12 million salary coming his way in 2015 (plus a 2016 club option for the same amount). I think most people would be indifferent to Dickey staying or going, since he is a joy to watch at times and isn't that expensive, but still takes up a rotation spot and occasionally gets into some nasty bad streaks. If the team was ready to aggressively promote some of its young arms, then the Dickey salary would go a long way towards plugging some of their other holes.
The next category of players that might make the team better if they weren't in Toronto next season would be the club option group. Brandon Morrow ($10 million), Adam Lind ($7.5 million), J.A. Happ ($6.7 million), and Dustin McGowan ($4 million) all bring their own positives to the table, but in many of their cases the money could be better spent elsewhere. Brandon Morrow has done nothing but sit on the disabled list for much of the past couple years, while Adam Lind takes up a roster spot while only playing against right-handed pitchers. J.A. Happ and McGowan can be replaced fairly easily for a similar amount of money so it's really up the front office whether they feel comfortable having them on the team next year. If the team wants flexibility in the form of financial and positional freedom, then some of these players would be better on different teams next spring rather than handcuffing the Blue Jays.
Personally, the best "addition by subtraction" option currently on the Blue Jays is Jose Reyes. He's fun to watch and often provides a spark within the team, but his salary is tying the hands of a front office that already has them pretty tightly bound by their bosses (or you could believe that they don't). Shortstops aren't the easiest things to find, but freeing up all that salary would be well worth the risk even if the team doesn't believe Ryan Goins is the answer going forward. The Cubs have more young shortstops than they have seats in Wrigley Field so maybe Anthopoulos can try to deal some experienced veterans to the team in return for a Jose Reyes replacement.