1941 - Take a good look at his eyes and think about that dark alley I mentioned.
Harold once killed a member of the Purple Gang in Eastern KY over a load of bootleg whiskey. Harold did time for that murder, but it still sparked a rather large war between Cleveland and Detroit. Moe Dalitz (one of the founders of LV)keep Harold alive for this murder. It was not his only murder but it was the only time he did TIME.