I don't quite understand the fascination with Bayless--he's really a SG in a PG's body, and even though he's increased his assist rate he's also increased turnovers. Didn't play much defense last year, really average at best when he tries. Best asset is his driving ability and ability to get to the line. I get the allure that he's super young and was a lottery pick hyped up with great scoring ability, but to me that's just an illusion. But in a team that's desperate for a guy who can seriously drive to the basket, he might actually get some run. But then again, I thought that was the case in NO as well, and then a month later he gets traded--tells you what they think of his upside.
As for the trade itself, it's not groundbreaking for either team and can be considered a wash. New Orleans in particular I'm not sure if this was great--trading Peja means they're investing in a guy who might be playing too many minutes (Ariza) given that he can't shoot. Jack is as solid as it gets and ranks as one of the better backup PGs in the league now, but come on, with CP3 being a minutes sponge was this necessary? He's a chameleon though, can adjust to what the situation calls for, can play both guard positions effectively. David Andersen is an absolute bust, and Marcus Banks' career has been irrelevant since about five years ago. NO must be super high on Jack if they're willing to sack Peja's useful expiring for that.
Toronto gets Bayless, and I think that since DeRozan's struggling, Weems is inefficient and Calderon is the only PG, Bayless can get minutes here. Moreover, Bayless moves from a slow-pace team to an above-average pace team, so he can thrive here as well in his one trick of driving and maybe pick up some dimes along the way. Peja actually was a decent defender last year--I think he's slightly underrated in this area, even between his chronic injuries and lack of diversity in his game. But a veteran presence. So ultimately not sure who wins out here.