Was Montana ever really a criminal ?
Doesn't sound like it,yet he was an important member of the Buffalo Family
How did he get in with those guys and rise to such a high level in the first place?
From what has been written about him, he was indeed. Maybe not a 'roll-up-your-sleeves' street hoodlum like many, but from what is known about him, for years, Montana was among Buffalo's most important mafioso. At one time, (if memory serves me correctly) John Montana supposedly actually served as the overall "Capo Famiglia" of that borgata before later stepping down in favor of others.
But his strength --- as we know --- came from his ability to infiltrate business and government, so, in a very real sense, he could be considered the MOST important and accomplished criminal of their entire Family.