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Born in Tampa, Florida, he attended Jesuit High School where he was voted Class Wit. After graduating magna cum laude from the University of South Florida in 1980, where he was a member of Sigma Alpha Epsilon fraternity, Lionel worked as a District Aide for Florida United States Senator Richard "Dick" Stone and in his unsuccessful campaign for reelection. Lionel graduated from the Stetson University College of Law, and as trial lawyer worked as both prosecutor for the Hillsborough County Florida State Attorney's Office (13th Judicial Circuit), and a criminal defense trial lawyer thereafter. He is admitted to practice law in Florida, New Jersey and New York as well before the U.S. Supreme Court.
He began his radio career hosting a show at WFLA 970 AM in his hometown of Tampa from 1988 to 1993. The Lionel Show debuted in Tampa, Florida, on weekends on 970 WFLA in October 1988. For years, Lionel had been a frequent caller to local shows, eventually becoming a "chronic", which is industry vernacular for frequent callers. He was noted for using various aliases and personas to get on the air. His most enduring moniker, "Lionel", alludes to Francis Lionel "Lion" Delbuchi, the character played by Al Pacino in the movie Scarecrow.
When WPLP (WFLA's rival station across Tampa Bay) offered Lionel a talk show, he declined, due to WPLP's rather meager offer—and his trepidations about how a radio show would affect his law career. In October 1988, WFLA management gave him an irresistible offer to move behind the microphone as a Sunday afternoon radio host. In January 1989, his show moved to middays (9 a.m. to 12 p.m.), Monday through Friday. Seven months later, he took the afternoon drive slot, where his lively mix of current events and dry humor proved to be a ratings success. In 1993, he was hired away by WABC 770 AM, a major talk radio station in New York City when a former ABC network president, Jim Arcara, heard Lionel's show while vacationing in Florida and lured him to the Big Apple. Lionel manned the morning drive slot on New York's heritage WABC 770 AM in early 1994. He set ratings records for WABC as its morning-drive host during the mid-1990s. For a time, Lionel did both morning drive and afternoon drive for a period immediately following talk radio legend Bob Grant's departure from WABC.
In the late 1990s, toward the end of his tenure at WABC, Lionel also hosted the CourtTV law show Snap Judgment. He also provided daily updates on WCBS 880 AM during the Clinton impeachment process. In 2000, he began his national radio show, The Lionel Show, originally syndicated by Premiere Radio Networks through 2001. His show was then syndicated by independent Rex Broadcasting until 2003, when it was picked up locally and nationally syndicated by the WOR Radio Network in New York City. It was broadcast six days a week (9 p.m. to midnight ET weekdays, and 5 to 8 p.m. ET Saturdays). In 2000 and 2001, in addition to his radio work, Lionel was a morning host on an Internet-based talk radio site, eYada.com until 2001.
Talkers Magazine included Lionel In their list of Talkers Frontier Fifty and the "HEAVIEST HUNDRED: The 100 Most Important Radio Talk Show Hosts in America" at number 23, and estimated the show's audience at 1.75 million unique listeners per week. The magazine described him as "a uniquely witty and intellectual personality" and "defying categorization".
He released a comedy album titled You Don't Look Like You Sound in 1996, and fronts a bluegrass band called Lock 'n' Load.
Lionel wrote a book, "Everyone's Crazy Except You and Me...And I'm Not So Sure About You: America's Favorite Contrarian Cuts Loose". It was published by Hyperion and was released on August 5, 2008. On March 22, 2010, Lionel began a nightly commentary on New York's WPIX Channel 11 and was a regular contributor to the morning and late night newscasts, as well as the station's legal analyst. He then launched LionelMedia.com on June 23, 2010, containing podcasts, audio, video, essays as well as his YouTube channel "Lionel Nation." In August 2012, Lionel began hosting the morning show on The New IQ 106.9 in Philadelphia. In 2015, Lionel began regularly appearing on RT and RT America as a legal and media analyst.
Lionel has appeared on Court TV, PBS, Tribune Media, C-SPAN, CBS, ABC, NY1, BBC, Bloomberg TV, MSNBC, Fox News, CNN, CNBC, Newsmax TV, HuffPost Live, RT America, RT International, Arise America, Food Network, CrossTalk, The Alex Jones Show, Stone Cold Truth, Air America, Coast to Coast AM, SiriusXM, Cumulus, iHeartMedia, France's Canal+, Radio New Zealand, Rossiya 24, Radio Belgrade, NTV and 92nd Street Y.
Lionel also appears in the 2016 fourth season of the Netflix television series House of Cards.