The plot to kill Castellano was well thought out and heavily supported within the Gambino family, which i think Chicago meant. In all honesty though it seems it inflated Gottis ego too much, because it went perfectly more or less. Gotti got too into his role as boss, and way too into his media persona that heavily hit the Gambinos even after his life sentence. If it was true that Carlo wanted Tommy to be boss after Paul, i imagine it would have worked out alot better. But hindsight is a blessing, and for all we know Tommy could have been worse or just as bad as Gotti, or Paul may have even named Tommy Bilotti as boss.