He also explicitly stated in his first press conference that after 10 years a change is good, hence the reason there's a huge correlation between the core's FA timeline and his second 5 year contract. Assuming Theo leaves at that point, best case scenario would be Jed moving into his role and perhaps McLeod as GM (if he hasn't already taken a GM role elsewhere). theo said a lot of things at that press conference and he's very good with words and with explaining things, but that whole 10 years thing is overblown. he was miserable in boston and came up with an old quote from Bill Walsh to explain at his introductory press conference why he left a sinking ship that was going down in flames. (he also said "Every season is sacred" and talked about dual fronts, trying to win and trying to build at the same time at that press conference) by all accounts, he is not miserable here, and I can't see him leaving for at least as long as this team is winning divisions and giving him chances to add more jewelry to his collection. if it wasn't for his miserable relationship with ownership and lucchino (or, in other words, if he had a relationship there like the one he has with ownership here) i doubt he would've ever left. yet leaving after 2021 gives him the time to run the DNC for pending 2024 election against Trump Jr.