The thing about Jack is that when he was in Portland he was a below-average three point shooter (at best). Last year he shot them at 41%.
I'm not a huge Jack fan, but that kind of three point shooting off the bench really gets my interest. It'd be interesting to see him compete with Bayless for the backup PG slot. Or you just make Bayless the official backup SG. Having Bayless and Jack coming off the bench would make a nice physical tandem.
He's far from my first choice, but I could live with him if the price is right.
Unfortunately, he's owed $15 mil over the next three years. That's a pretty steep price for a backup PG.
I'd do a straight-across swap for Webster. (We could call it the Chris Paul Trade, since the two combined are worth Chris Paul!) Don't know if they would. I wouldn't if I were in their shoes.