Senatus autem, mi Brute, fortis est et habet fortes duces. Itaque moleste ferebat, se a te, quem omnium, quicumque fuissent, fortissimum judicaret, timidum atque ignavum judicari. (Cic., Fam. XI, 18)
Can anyone tell me why judicaret is in the subjunctive?
Independent clause in indirect discourse, so subjunctive, I would say.
Clausula independens per orationem obliquam, tunc modo subjunctivo, dicam.
The “fortissimum judicaret” is not parenthetical. The fact that they judged him the best is precisely what makes it so hurtful that he criticise them now. So it must go into the subjunctive.