The Bulls have that obvious hole at shooting guard that all of Bulls nation is trying to fill. One name that fits pretty well, but hasn't been publicized is Leandro Barbosa.
One of the primary problems in trading for a SG is that to match salaries the Bulls typically need to give up Ronnie Brewer or C.J. Watson, giving up Watson leaves them without a backup PG, trading Brewer often leaves them without really upgrading SG significantly (or possibly at all) as they typically lose defense.
This trade helps solve both problems.
Why for the Bulls
For the Bulls, Leandro Barbosa can play as the back up PG while Rose is out. He can run a high octane fast break oriented style of play and create his own shot. He can play C.J. Watson's role at least as well as C.J. Watson.
He can also come in and play minutes at SG as an offensive option for the team. He's a quality shooter over the course of his career though his percentages are likely helped from a large percentage of open three point shots created in the Suns offense.
Barbosa allows us to use Watson rather than Brewer in a trade, because he's a 1/2 option rather than a 2/3 like most of the SGs we've looked at.
Why for the Raptors
As for the Raptors, the trade makes some sense as well. Barbosa is a pretty expensive player relative to his value. The cost isn't long term (just one more season when he picks up his player option), but it's still 7 million for a player who's not giving you 7 million in value.
They save quite a bit of money this year on the trade as well as having large savings next year. They also replace Barbosa with Watson who can fulfill Barbosa's role in a more wide open offense. They Raptors also wanted James Johnson during the draft, and would have more playing time to offer him. While Johnson hasn't hit his potential here, he's flashed enough signs that he may still interest them as a prospect, especially given how hard he's worked and how little opportunity he's had.
Why it may not make sense for either team
The overall talent in the trade is pretty similar. My fear with the move is that C.J. Watson might actually be as talented as Barbosa, but stuck in a system that doesn't fit him as well. However, Barbosa may end up stuck in the same way as Watson, as much like Watson, he's a player who's used to running more, taking more risks, and creating his own shot.
Would Barbosa play as well as an off ball SG? Would he run the offense as the backup PG or have the freedom to create on his own and be himself?
On the surface, it's a deal that's close for both sides. I doubt it elevates the Bulls to championship contenders, but it does give them one more pure offensive player, and remove their biggest hole currently (Brewer or Korver would start with Barbosa playing the energy role off the bench).
As for the Raptors, they're giving up the best player in theory. Is minor cash savings and James Johnson as a prospect worth it to them? Sure they're not in win now mode, but they're also no where near the luxury tax, so the cash savings isn't that important either. Unless they really believe in Johnson or Watson, the move may not make much sense to them.
Ways to tweak the trade
If something like this was discussed the most likely concession would be the Bulls tossing in their 2011 1st or some cash to help push Toronto over the edge. They might demand back a second rounder if they give up their 1st though.
On the surface, the trade makes sense to both sides to me, particularly if you throw in a Bulls 1st and a Raptors 2nd. The Raptors get a little more ammo in their quest to rebuild while losing a player that's likely not helping them much in the future anyway and saving some cash.
The Bulls upgrade the talent on their roster and fill one of their holes in as well as add another legitimate offensive threat to the team which is dominating on defense but average on offense.