Milton "Maishe" Rockman was the Meyer Lansky of Cleveland. He was also married to Boss John Scalish's sister and Scalish was married to Rockman's sister. He was a top advisor to John Scalish, but was never made because he was Jewish. He was very close to Bill Presser from Cleveland, one of the most powerful members of the Teamsters Union and a conduit to the Central States Pension Fund. Maishe was as close as one could get to being made, he was also brother in laws with Underboss Angelo Lonardo, as Lonardo was married to Scalish's other sister.

Rockman was with Scalish on his deathbed and after Scalish died, Rockman said it was his dying wish to have James "Jack White" Licavoli as his successor, which everybody in Cleveland, Detroit, Pittsburgh & Youngstown knew this was a lie and that Lonardo should have succeeded his brother in law as boss. The reason why Rockman did this is because he and Angelo did not get along, as Lonardo was old school and never allowed Rockman in on "family business" with other LCN families. This always was a source of tension for the two, as Lonardo would have him walk away from the table when sensitive conversations were to take place with other representatives from families like Chicago, Milwaukee & KC. Rockman knew that James Licavoli would listen to him and that he would be easier to control than Lonardo.