Although the consensus in the comments on a previous post seems to be that Rudolph Valentino would have had nothing to do romantically with Marilyn Monroe, a connection does exist between the two. In Affairs Valentino I wrote about Joseph Schenck's stint in prison and his presidential pardon. But it was Schenck who, after his pardon, promoted Marilyn and gave her the first breaks in film. It is still rumored they were lovers.
Schenck and his United Artists, produced Valentino's finest films, The Eagle, The Son of the Sheik. Schenck certainly did not discover Valentino but he elevated his films, imo to a higher degree and also made him a very wealthy man. The story of George Ullman v. Joe Schenck after Valentino's death is a gripping one which I also covered and analyzed in Affairs Valentino.
Schenck was said to have also discovered Marlon Brando and there is no doubt his long history in Hollywood connected some of the greatest stars; including Valentino.
And in the “what if” musing/discussion, I think Valentino might have been interested in Marilyn because she was such a huge star. If only for a fling. But the powerful Mr. Schenck played a major role in both Valentino and Monroe's life. Monroe and Schenck as a couple... oh dear I think not. (see below)