Soon after the Harvard Inn opened, Yale married Maria Delapia, with whom he would have two daughters, Rosa and Isabella. They later separated, he married a younger woman called Lucita in 1927 and they had a daughter, Angelina. Yale was also noted as a stylish dresser, favoring expensive suits and diamond jewelry. One newspaper reporter called him the "Beau Brummell of Brooklyn". Yale was also known for generosity toward the less fortunate people in his neighborhood, who often approached him and requested financial assistance. After a local delicatessen owner was robbed, Yale replaced his lost cash. When a fish peddler lost his cart, Yale gave him $200 with an admonition: "Get a horse, you're too old to walk". Yale was dubbed the "Prince of Pals".
In a last-ditch effort to mend the relationship with his longtime friend, Capone invited Yale to Chicago to view the Dempsey-Tunney heavyweight title rematch at Soldier Field on September 22, 1927. While their visit was civil enough, the pair's friendship began to rapidly deteriorate after Yale returned to New York. Distracted by a gang war with rival mobster Joe Aiello, a brief exile from Chicago, and the 1928 Republican primary election, Capone had to wait until the spring of 1928 to plan retaliation.