I also would pick Conn. Billy wouldn't try any toe to toe stuff with this guy I'm sure! From the slight training footage of Greb we see a very fast with his hands and feet middleweight and his record shows not much of a ko punch. Billy could likely match him speed wise and nicely out box him.
I don't disagree, but why was Greb able to really beat up Gene Tunney, and why wouldn't he be able to do the same thing to Conn?
From what I've read, the rough Greb took the young Tunney to school in the first fight...and gave him the beating of his life...Tunney won the second fight, but it was a disputed decision.