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Conrad Black speaks in Toronto on May 14, 2013.FRED LUM/The Globe and Mail

Toronto Mayor Rob Ford has a date with Conrad Black.

The city's embattled mayor will sit down with the former newspaper publisher for a segment on Mr. Black's show that airs weekly on Vision TV and is targeted at the over-50 crowd. The show promises to be an interesting conversation between the erudite Mr. Black and a mayor who has built his reputation as a scrappy regular man who doesn't have time for the so-called elite.

It's also a pairing of two men trying to redeem themselves following considerable setbacks – Mr. Black spent time in an American prison after being found guilty of fraud and obstruction of justice and Mr. Ford is trying to rebuild his reputation after admitting to using crack cocaine and having a problem with alcohol.

Vision confirmed the mayor would appear on the show, which is cohosted by Denise Donlon and airs on Monday nights, but didn't confirm which night it would air.

Mr. Ford knows what he's walking into – Mr. Black has already come out swinging against Mr. Ford's critics in a column written in the National Post in which he suggested the mayor should simply "be more careful, including the avoidance of inflammatory malapropisms."

"But nothing has come to light that disqualifies him from fulfilling the mandate his electors gave him, and I do not believe that the City Council has any legal capacity to redefine the powers of the mayor, unless the provincial legislature assigns the authority over municipal government to the Toronto Star, shelter for rabid editorial writers," Mr. Black wrote. "No sane person could imagine that the City Council is a teeming hotbed of Tocquevillian champions of disinterested local government, and no one has conferred any power of usurpation of legally attributed powers on those who fester in the council."

The mayor has been a regular on the U.S. television circuit since he became enveloped in scandal, but hasn't given many Canadian interviews aside from an interview with Peter Mansbridge on CBC. He's preferred to handle his own media – he had a weekly radio show on a Toronto radio show until recently and Sun News Network gave him a show that lasted one episode.

Sun News said it took four hours to shoot and eight hours to edit the one-hour show, which is more than usual and meant the show wasn't financially feasible to produce. Mr. Ford responded by vowing to start his own YouTube show with his brother, Councillor Doug Ford. The brothers said they turned down offers to from the likes of Dr. Phil and Oprah Winfrey in opting to produce their own show, which they hope to release on YouTube by the end of the year.

With a report from Elizabeth Church