Leonard would be very tentative, moving alot and pot-shotting, he wouldn`t be landing much but his hand speed would bother Jake, LaMotta had fast hands too, his fast jab would bother Ray and he would throw more of them like he did v Robi in their final clash which could be a huge factor in this fight.
Ray would have to kill Lamotta's body much like SRR. Jake relentless, he'll eat punches all day and still suffocate you w pressure. All in all, I'll take Leonard.
If Leonard tries to slug and be macho he could be in trouble. However if he boxes he wins by a mile. La Motta was not a huge puncher and Ray took a good punch and otherwise would be too quick IMO. Could make a difference if over 15 rather than 12 rounds but it is not like Ray wasn't also a 15 round fighter.