The Holiday House was a well known Mob hangout in Monroeville,Pa.
It featured top shelf national talent. The Feds suspected,but couldn't prove,that Pittsburgh Boss Mike Genovese was a secret owner.Around here,you went to the Holiday House on your birthday,or your graduation,and it was a big deal.

What probably happened was that Chicago contacted the Pittsburgh Family,explained the situation,and got an OK for Leno to do their gig. I would imagine that a piece was kicked back to Pit out of respect.

By the way,the Holiday House closed in 1988,so that would narrow down the identity of the gangster that Leno mentioned.