In this episode, Gianni and Jeanie welcome co-author Michael Benson as the discussion revolves around Benson’s new book about Carlo Gambino, along with his previous collaboration with the host on various organized crime books. Benson shares insights into his journey into writing about gangsters, starting with a chance encounter with Frank Damario and editing his book. He details the process of writing about Carmine Persico, Albert Anastasia, and other notable gangsters. The conversation also touches on personal anecdotes including Benson’s background and experiences, as well as the Gianni’s reflections on growing up surrounded by organized crime figures.

Gianni and Jeanie interview Tony Orlando, who recounts knowing Russo since around 1980 and praises Russo’s legendary storytelling and Las Vegas speakeasy era. Russo shares stories from his youth, including selling ballpoint pens after polio and meeting Frank Costello, plus his real-estate connection to O.J. Simpson’s Rockingham house. Orlando and Russo discuss shared connections to John Catsimatidis and the Copacabana, where Orlando says his uncle Carmine Fava was maitre d’ and where Orlando witnessed performers while underage. Orlando tells personal stories involving Crazy Joe Gallo (including being invited to Gallo’s home and seeing a pet lion), his early hit at 16 (“Halfway to Paradise” written by Carole King), and friendships with major entertainers. Orlando describes working at CBS with Clive Davis as a vice president, signing artists like Barry Manilow, and later achieving major success with Tony Orlando and Dawn, including “Tie a Yellow Ribbon,” a TV show watched by 36 million weekly, and a Phyllis Diller on-air moment where her wig came off. He shares multiple Frank Sinatra anecdotes, including Sinatra correcting his diction, recording “Tie a Yellow Ribbon” for John Wayne, arranging a star-studded Friars Club event honoring Gene Kelly, and a Caesars Palace night when Sinatra learned his mother’s plane had crashed. Orlando explains he retired from touring concerts due to travel and overhead but is launching a storytelling show and considering a book or audio format; he also notes work for eight presidents and other career highlights. The conversation ends with Russo promoting upcoming New Jersey appearances and book signings, and Orlando describing his WABC radio show and longtime veterans charity work through his Tribute to Valor Foundation, which brings Medal of Honor recipients to schools and has reached about 100,000 students.