Eddie, I'm going to offer up some advice sorta like Curly Dave and you can take it for what it is worth. If you do or don't get Oscar fixed, you need him in a pen when you are not home. If you can't do that, you need a big liability added to your homeowner's policy. The next time he is out on the highway, someone may have an accident and now the local law enforcement knows exactly who he belongs to. This wakeup call is a dirt cheap warning. Paying for somebody's car and hospital bills may be next. Oscar is smart and will follow when you leave because he is used to following you around your place and playing. It's just natural for him to see you go down the driveway and follow. When he gets to the road, he's not afraid of those cars because he has been playing with you and the Mule and that's all he knows.
You may be thinking the same thing and planning an enclosure, but I'd get one of those dog kennels and put an electric wire/fence charger around the bottom to discourage Oscar from digging out. If he ever does escape again, you'll have the pen to show that you actually tried to restrain Oscar.
Maybe I'm a bit more sensitive than some, but Kathy had a pet dog that killed himself when a neighbor's pig came calling. The pig ran back and forth outside the inner dog fence and her dog went nuts chasing the pig. The pig was just playing with the dog because he was smart enough to know he could not get out. Finally, the dog found a tight spot in the field fence at the corner post and forced his head through, but could not get it out. The dog strangled himself in the fence. Lots of things can happen when animals get loose. They are fun and great to have, but there are times you just have to contain them. When you come home, let Oscar out and play, but put him back in that pen at night or anytime you are not there. It's for his safety and everyone else's safety.