Ike Evans, owner of Miami's most glamorous hotel, needs his 1958 NYE concert to be a smash. He makes a deal with mobster Ben Diamond to ensure success that threatens his life and family.

Ike tries to bribe officials to legalize casino gambling. An old friend visits Vera, and Ben wonders if his wife is faithful. Ike contacts his wealthy ex-sister-in-law for a favor.

Mike Strauss' body is seized, Ike reacts to a break-in, and Victor plots to get his wife out of Cuba. Vera secures Jackie Kennedy for a charity event but laments not having children with Ike.

Ike is determined to save Judi Silver from Ben Diamond. Polaroids of Stevie and Lily surface. Vera tries something new to get pregnant, Danny and Mercedes' bond grows, and Klein's search ramps up.

Ben and Ike bet heavily on a boxing match and Vera receives another cancellation from Jackie Kennedy. Meanwhile, Danny receives photos intended for Stevie and the DA makes an important discovery.

Things are going badly for Ike: Meg turns down his offer, he is caught lying to Ben and Klein shows him damning evidence. Meanwhile, Stevie's affair comes back to haunt him.

Lily and Stevie's affair becomes dangerous for them both and Judi finds herself in Klein's hands.. meanwhile, Mercedes and her father receive some bad news.