Rationale: Chicago has a hurt Derrick Rose for the year and in my mind would LOVE an expiring player in the mold of one of the best distributors in the league. The team defense Chicago is known for will definitely hide Calderons deficiencies. I honestly see no better talent filling in the PG spot for Chicago, i see Calderon as meant for the bulls.
Ed Davis is also a delicious part of this deal, joining Taj Gibson, Joakim, and Boozer within the rotation, this would be the grittiest and most defensively savvy front court in the league, bench and starters! Bonus is the amount of money shed, Ed is only 3 mil, Calderon is an expiring 10 million they would love for next off-season!
For Toronto, Loul Deng is the answer at SF, we clear PF jam, and get good return value for Calderon who is likely gone soon (if not now, at mid-season). Loul is known for both his defense, and his savvy veteran presence on offense. Still young enough to contribute for the next while and would officially change the face of this team. Negatives include his contract of 13 million.
Though Chicago would probably need to improve their wings now, they could probably use the flexibility Calderon gives them next summer to get a stronger wing ready in time for Derrick Rose's return! Hopefully younger and cheaper then Deng.