I really like Rudy Gay a lot. However, I wouldn't trade Rondo for him straight up. Rondo fills a position of need, and could fill it for the next decade.
Rondo for Gay + the #2, I'd do.
Rondo for Gay + Conley, I'd think about, and probably do.
Rondo for Gay, I pass.
You'd lessen our chances of winning the title to pick up Gay, or even Gay and the #2?
I'm not sure that Gay + Conley, or Gay + #2, really would lessen our chances of winning, especially if we added a veteran free agent. We may downgrade at the PG position, but we'd be getting a huge upgrade elsewhere.
I mean, you were one of the members who thought we'd win the title with a healthy KG this year, right? Well, if the only player you subtract off this year's team is Rondo, and you add Mike Conley, Rudy Gay, and Antonio McDyess, wouldn't that amount to a net upgrade? (That presumes you either re-sign BBD or replace him with a comparable talent).