The Mighty 1090's morning show, Sileo was named once again to the Talkers Magazine's Top 100 sports radio shows in America at number 93 in 2014 after tripling the ratings. In March 2015 and 2016, Sileo was named radio pregame host of the San Diego Padres. In October 2015, the Little Italy Association of San Diego honored him as one of America's most famous Italian Americans by adding him to the legendary "Banner Program". In 2015 Sileo was named number 29 by Talkers Magazine, among the most important SportsTalk Radio shows in America. He was also named #16 in Jason Barrett's Top 20 Morning Sports Radio Shows in America. He was named to RadioInk's Top 30 Local Sports Radio host in America at number 24. In 2016, the Football Writers Association of America (FWAA), invited him to vote weekly on the SUPER-16 Grantland Rice Poll which teams up weekly with the National Football Foundation (NFF). Again in 2016, he was named to the Radio Ink Top 30 SportsTalk radio shows in America, he came in at #21. He started out 2017 year being named #20 on Jason Barrett's Top 20 Morning Sports Radio Shows in America. He named to the 2017 Talker's Top 100 Sports Talk Radio shows in America in at #31. He was one of the few ex-pro athletes hosting a morning sports radio talk show as a solo host in America. In 2018, Sileo once again was named to Radio Ink's Top 30 SportsTalk radio host in America. In January 2018, Sileo left "The Mighty 1090am" morning drive show for Entercom's new talk and sports station on 97.3 FM "The Machine" from 10am-2pm doing general talk radio. One month later, Entercom re-branded the station as "97.3 The Fan." Sileo returned to morning drive 5am-9am. In April 2019 Sileo left the morning show on 97.3 FM, but remained with Entercom Communications for several more months. In August 2019, he was hired by IHeartMedia to host afternoons on Fox Sports 910 KGME in Phoenix. But the program was discontinued the following week due to pressure from the Arizona Coyotes hockey team. KGME carries the Coyotes and team management felt Sileo's past controversial remarks on sexuality and race were not a good fit with the team's flagship radio station. In September 2020, Sileo started a new nationally syndicated radio show on the USA Radio Network. In April 2021, Sileo started