Schlesinger was the unsuccessful Republican nominee for the United States Senate in 2006, finishing third behind third-party winner Joe Lieberman and Democrat Ned Lamont.

In 2013, he announced that he was running in Florida's 18th congressional district in the 2014 elections; however, he finished in second place for the Republican nomination behind Carl J. Domino.

In April 2006, Schlesinger announced his intention to run for the U.S. Senate seat held by Joe Lieberman of the Democratic Party, with a pledge to spend $500,000 of his personal funds on the campaign.

Many contended that the scandal would jeopardize Schlesinger's Senate campaign, and fellow Republicans, such as Governor of Connecticut Jodi Rell, suggested that he withdraw.

"[10] Throughout the campaign, Schlesinger was considered a longshot, and many Republicans declined to support him, turning instead to Lieberman, who ran and ultimately won as an independent candidate after losing the Democratic Party's nomination in an August primary.

White House Press Secretary Tony Snow also stated that the Connecticut Republican Party suggested that "we not make an endorsement in that race and so we're not.

[17] In an article published on August 4, 2014 by George Bennett of the Palm Beach Post, Schlesinger stated that an internal poll conducted by Cherry Communications showed that 53% of potential voters in the Republican Primary were undecided at the time, so he decided to contribute $100,000 more to his campaign efforts.

[18] The Republican Primary for the Florida's 18th congressional district currently featured four other candidates besides Domino and Schlesinger: Beverly Hires, Brian Lara, Calvin Turnquest and Nick Wukoson.