The Raptors once had a similar type player in Chancey Billups. There was the same questions on what he was. Is he a point guard? A combo guard or a under sized shooting guard. Ultimately the answer was not found in Toronto but in Detroit were "Mr Big Shot" was born playing at the point for a championship team with the Pistons. While you would like to believe and hope that Bayless could find a path to his true identity as a NBA Player, you also have to wonder how long you are expected to wait. Watching Bayless can be a truly frustrating experience at times. He can make a true great spectacular play and the next time up the floor a totally unexplainable turnover. "His Gift" as Dwane Casey refers to it is his ability to score and get into the paint. It can also be his curse at times. He sometimes will call his own number and end up with a highly difficult attempt instead of making the simple pass and the smart play to a open player.
What makes this all the more frustrating and puzzling is I would venture to say Bayless is one of the most intelligent people in just terms of brains in that locker. Taking that to the basketball court, that intelligence is sometimes clouded by his competitive fire. He absolutely hates to lose and gets personally disgusted by the experience. On top of everything he is a nice young man that truly has embraced Toronto and legitimately loves the city. We would kill for more people who felt that way in the NBA that want to play and live in Toronto. Yet it really seems like a hard choice to make based on basketball alone.
In addition to Bayless there are other guys like Maglorie, Aaron Gray to decide about. I am not sure there is anyway you can see both Aaron Gray and Jaamal back. It would seem to make little logic to do so. There is already lots of speculation that Maglorie will return and he is even making playoff guarantees on behalf of the team. I would see this has a slap in the face to Aaron Gray if he ends up out and Jaamal in. Gray has done more in terms of on the floor and seems the perfect fit to play back-up 5 minutes behind Jonas Valanciunas. It is not like Aaron Gray is going to be worried about minutes. Although unlike Jaamal he can log major minutes if required. So, if you have Valanciunas having troubles adjusting to NBA game in terms of picking up fouls, Gray is able to plug in and fill those minutes. If Aaron Gray was from Toronto and Jaamal was from Charlotte this is not even a conversation. People will deny it, same as they did with Jay Triano but the Canadian passport that Magloire has gives him added value as the organization might view it from a PR point of view. He is well spoken and many respect what he has accomplished making it to the NBA out of the Raptors home town. Still numbers don't lie and the Raptors attendance did not trend upwards by bringing home the hometown hero. The simple fact as I have stated many times is the hometown hero stopped being an effective or at least significant NBA talent in 2003. I find his song and dance about his pride for playing for his hometown team to be somewhat hypocritical, as he likely had several chances to come here sooner than he actually did. Ultimately ask yourself this question. If Aaron Gray or Jaamal Magloire is cut loose by the Raptors who likely is still in the NBA next season. The answer is Aaron Gray who always seems to find a landing spot despite not being able to find a long term home in the NBA.
Aside from those mentioned you have Solomon Alabi, Ben Uzoh and Alan Anderson all without contracts heading into next year. In terms of Solo it was kind of nice to see him finally get a chance to play, but in reality there is little chance he has a future with the Raptors or in the NBA. The Raptors have consistently failed to find gold in the second round of the NBA Draft and he is just the latest example of that. He seems like a great person and is well liked by everyone but ultimately is like the last kid that is picked in a pick up game on a school yard in NBA Terms. Both Alan Anderson and Ben Uzoh to a lesser extent have made claims that they belong in the NBA. That said given the high expectations for this off-season if it is with the Raptors it would be viewed or should be viewed as failure on Colangelo's part to upgrade the talent on this roster.
Just because you have a contract that doesn't leave you safe either as the Raptors do have some attractive contracts they could easily move if they so desired to do so, on guys like Gary Forbes and others. Even Amir Johnson's deal is not unreasonable by the standards of what a solid power forward is going for these days in free agency. Colangelo's flexibility gives him options, but it also gives most of this roster insecurity. Aside from Calderon, Bargnani and perhaps DeRozan it is easy to see anyone being moved. Even under the right circumstances these 3 could be moved as well but it would be highly unlikely based on the comments of Colangelo today in his press conference.