The mistake he made with Benny Blanco was one thing. Heat of the moment misjudgment, etc. But he had to know that a mafioso wasn’t going let Kleinfeld live after stealing a million dollars from him. No way he could have been that naive.
Likewise, why would Tony T risk his escape by relying on Kleinfeld?
Great movie, but this plotline was too irrational.
Fair points.... but here's my take: Carlito essentially felt like he owed Kleinfeld his life so even though he knew it was an insane thing to do he went along because he felt honour bound.
As for Tony T - they tried to lampshade this a bit when Kleinfeld says he's been 'sailing these waters for 20 years' implying that he had the skill and the means and nobody else Tony T controlled did. It is hard to believe that only one of Tony T's crew went along to help, there's no way around that, but I suppose you could say they underestimated K and assumed they wouldn't need to get anyone else involved.