Not really, I can't think of many times where they've picked a bad film butfar too afraid of controversy and thus in hindsight they're almost always wrong. For example in Streetcar Named Desire (Marlon Brando's first role) everyone except Marlon Brando won an Oscar for acting. Similarly for director's Kubrick never won, Welles never Won, Lynch has never won, Bergman never won, Hitchkock never won, Kurosawa never won and Tarentino hasn't won.
Even when major directors do win it's rarely for their best work, often it's something they do when they're older and their past work is viewed more favourably (or at least with less controversy) so often they win it for films that are clearly inferior to their earlier work, sometimes this doesn't go so badly like with Clint Eastwood's Unforgiven which is easily his best film.
Even when major directors do win it's rarely for their best work, often it's something they do when they're older and their past work is viewed more favourably (or at least with less controversy) so often they win it for films that are clearly inferior to their earlier work, sometimes this doesn't go so badly like with Clint Eastwood's Unforgiven which is easily his best film.