Robert "Bobby O" Olszewski (born September 6, 1977) is a former American politician who previously served as a member of the Florida House of Representatives, representing the 44th District which included Windermere, Winter Garden, Gotha, Lake Buena Vista, Oakland, parts of Ocoee, and the Dr. Phillips, Horizon West, and Williamsburg communities in Southwest Orange County.
[1] The district contained Walt Disney World, Universal Studios Florida, SeaWorld, International Drive, and the Orange County Convention Center.
After graduating from Dr. Phillips High School in Orlando, Olszewski earned an undergraduate double major from the University of Central Florida in Radio/Television (B.A.)
[9] Olszewski additionally served as a television analyst for Spectrum News 13[10] and WFTV ABC 9 in Orlando, the nation's 15th largest media market.
[14] Olszewski was the only Winter Garden Commissioner to vote against removing prayer from the commission meetings stating his vote was “the most indicative of defending the Constitution.” [15] When Major League Baseball's Houston Astros and Washington Nationals were looking to leave their respective Spring Training homes in the Florida Grapefruit League, Commissioner Olszewski reached out to both organizations about moving their Spring Training to Winter Garden.
[19] Olszewski was runner-up [20] for the Orange County Commission [21] race in District 1 [22] where he was endorsed by Major League Baseball All-Star and World Series Champion Johnny Damon and Joey Fatone of N Sync.
[23] After Eric Eisnaugle was appointed by Governor Rick Scott to serve as a judge on Florida's Fifth District Court of Appeal, Olszewski won the Republican primary in the special election.