Over his three-decade career as New York City’s most notorious transit enthusiast, Darius McCollum has become an urban folk hero to some for his habit of posing as a friendly transit worker, driving buses that do not belong to him and taking city subways for joy rides. He has inspired a play. Someone is filming him for a new documentary.

Yet several people who had been close to him said they gave up on him after repeatedly watching him leave jobs and therapy programs, always ending up behind bars again.

Now Mr. McCollum, 48, who has Asperger syndrome, may have another chance at help, if he wants it.

On Wednesday, when Mr. McCollum was supposed to be sentenced in Queens Criminal Court for stealing yet another bus, his lawyer said he was likely to be paroled and sent to a residential treatment program with a long-term, detailed therapy plan.

It is the first time such a structured approach has been tried, said the lawyer, Sally Butler, who noted that participation in the program would be a condition of parole.