Sileo started his sports career at Stamford Catholic High School (now Trinity Catholic) in Stamford, Connecticut. He is the highest drafted NFL player from Stamford, where he led Catholic High to two straight city crowns, was named All City three times and was also named 1st team All-State in football by the CIAC and 2nd team All-State by the New Haven Register. Sileo made the Adidas High School All American football team in 1981. Before his current career, had a short NFL career as a defensive lineman, playing for the Tampa Bay Buccaneers, and appearing in preseason games for the Detroit Lions and the Dallas Cowboys.
Sileo transferred once during his college career. He started at Maryland, where as a freshman he played in 10 games and broke Hall of Famer (and former Terp) Randy White's freshman bench press record with a 435-pound press. Sileo was a member of the University of Maryland's 1983 Atlantic Coast Conference Championship football team. Sileo is reported to have been kicked out of school for throwing someone out a 1st story window on campus. Sileo would also that summer become a honorary member of the Hells Angels and ride with the Bridgeport, Ct chapter. He then went to the University of Miami Hurricanes to form College Football's Greatest defensive Line in Jerome Brown,Daniel Stubbs,Bill Hawkins and Sileo. In 1986, Sileo led the Hurricanes defensive line in solo tackles with 50 and 97 total and tackles for loss with 13 and third in sacks with 6 and first in fumbles with 8. In Sileo's games in 1986 vs. Florida and Florida State, Sileo would register 24 tackles 3 sacks and 5 tackles for loss. He was also the leading tackler in the 1987 Fiesta Bowl, where Sileo started the game off with a QB sack of Penn State QB John Shaffer; Miami fell 14-10 to Penn State with over 70 million viewers watching the Fiesta Bowl with a 24.9 share and 25.1% of households tuned in. He made All South and was an All-America honorable mention and 2nd team All American by Sport magazine in 1986. He was named to the Sporting News preseason All American team in 1987. Sileo in 1987 was a Sporting News preseason Outland Trophy & Lombardi Trophy candidate. Sileo is the strongest Miami Hurricane Football player of all time with a 535 pound Bench Press & 700 pound Squat. Sileo was named to Sports Illustrated's All-Time College Football Walk-On Team in 1992.
Sileo ran out of his five-year eligibility for NCAA play after the 1986 season. On September 6, 1987, two days after the NCAA deemed him ineligible, Sileo claimed that because he had not entered the 1986 NFL Draft, he was a free agent; he proceeded to sign with the Buccaneers. The NFL declared the contract invalid and put him in the 1987 NFL Supplemental Draft. Although Sileo initially sued the NFL and the Bucs to honor his original contract, he eventually submitted to the Supplemental Draft, where the Bucs selected him in the third round (59th overall). Sileo is the second-highest drafted defensive lineman in Supplemental Draft history. Sileo spent his entire NFL career as a backup and special teams player. The only regular season games he played in were during the 1987 season. Sileo was named to the NFL's Honorable Mention All-Rookie Team.
He eventually played for the Orlando Thunder of the World League of American Football in 1992, where he was a first team All-League, and helped lead the team to the World Bowl in Montreal, Canada, where they lost to the Sacramento Surge 21-17. His last professional team was the Las Vegas Sting of the Arena Football League in 1994, where he made honorable mention All League and helped lead the Sting to the AFL playoffs, where they lost to the Arizona Rattlers 51-46 to wrap up his pro football career.
Sileo was hired by San Francisco KGO Radio 810 where he was a sports anchor on the morning show called Dunbar and Rosie and was hired by former GM Mickey Luckoff. Sileo moved across the street to KNBR 680 were Sileo hosted "Sportsphone 68" and The Ticket 1050 where he hosted the morning show with Rod Brooks called Ebony and Ivory from 6-10am . He was also on the Oakland Raiders pre- and postgame shows and was the sideline reporter for Stanford Cardinal football and the San Jose Sabercats pre- and postgame host. In 1998 Sileo moved to Tampa, Florida to take over the morning show on 620 WDAE where he took the morning show over and raised the ratings for the show into the top 5. In 2000, he moved to Fox Sports Radio in Los Angeles, California, where he hosted a 4am-8am program called The Dan Sileo Show. Sileo was the first person hired by than CEO Kraig Kitchin in the network's history; he got the show to 233 stations. In September 2002, Sileo moved back to Florida and debuted on 740 The Team in Orlando. His program, The Dan Sileo Show, began airing from 6 a.m. to 9 a.m. Eastern, with an emphasis on hot topic issues such as race, drugs, and other sports scandals, as well as a typical morning wrap-up of the previous day's events. For a short time in 2004, the program was syndicated on WINZ 940 AM in Miami. On weekends, Sileo also has worked as an analyst on Westwood One radio.
In December 2007, 740 the Team began a format change. Sileo announced on-air that he had signed a new contract extension with Clear Channel to continue his show, but it would move down the dial to NewsRadio 540 WFLA. In January 2008, WQTM switched to a Spanish-language format, and The Dan Sileo Show settled into its new permanent home at NewsRadio 540 WFLA.
His last stop at 620AM WDAE in Tampa, Florida was as morning drive host from 1998 to 2012. Jacor former executives Gabe Hobbs and CEO Randy Michaels were major influences in Sileo's success and Michaels has called Sileo the best sportstalk radio host in America and Hobbs now represents Sileo along with Stuart Levin (www.GabeHobbsMedia.com). Sileo was syndicated in Orlando, back on 740 The Game (after that station changed back to a sports format). Sileo is also a Heisman Trophy voter, a member of the Football Writers Association of America and a member of the Atlantic Coast Conference (ACC) media. In 2011 TV sports columnist Jim Wlliams of the Washington Examiner wrote that Sileo is the best morning sports radio host in the country. In July 2012, Sileo was named to Talkers Magazine TOP 100 SportsTalk Hosts in America at #32.
His career has been marked by a series of several controversial events that led to his firing from three radio stations in 2012 and 2013.
Sileo was fired from WDAE-620 AM in March 2012 after he called three black NFL free agents "monkeys." The Tampa Bay Times reported that, while discussing the possibility of Cortland Finnegan, Vincent Jackson and Jonathan Vilma joining the Tampa Bay Buccaneers, Sileo said, "If they get those three monkeys, I'm good. I'm ready, man. I'm ready. I want those guys. Those guys are great players."
Sileo joined Miami's WQAM-560 AM in April 2012 but was fired in March 2013 after several public missteps. In January 2013, he was suspended from the station after a series of sexist tweets directed at Fox Sports broadcaster Erin Andrews. The Tampa Tribune reported that one of the comments referred to a 2008 incident in which a stalker secretly recorded a video of Andrews in her hotel room. Sileo tweeted to Andrews: "pepe [sic] hole best thing for ur career." He also referred to her as a "bimbo," told her to "make me dinner" and bake me a cake" and added, "love Erin either naked or in a porn..not at a sports desk." The Miami Herald reported that an on-air anti-Semitic remark on Jan. 30 was the decisive factor. The newspaper reported that Sileo's comment — "that's the half Hebrew in me" — regarding saving money prompted a letter of protest from the Anti-Defamation League. Sileo posted on his Twitter account that his grandmother was Jewish, “and because my grandmom is Jewish..my nfl friends lose all [their] money..i said.. ‘I save [EVERY] nickel I have and that’s the hebrew.”
Sileo joined Palm Beach's WMEN-640 AM in August 2013 but was fired on Nov. 4, 2013, after tweeting the previous day that he would pay $1,000 to any University of Miami football player that “TAKES THIS KID OUT” while attaching a photo of a Florida State University football player. FSU defeated Miami two days earlier. Sileo deleted the tweet, claiming he was only joking, but WMEN fired him. “As a result of Dan Sileo’s action on his personal Twitter account ... WMEN has terminated his independent contractor relationship with the station,” WMEN said on its website. “The ownership, staff, and management of WMEN 640 Sports do not condone his actions which have no place in sports.”
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