Winnipeg’s Sam Katz is giving Toronto’s Rob Ford a run for his money in the race for Canada’s most controversial mayor.

But Katz’s problems are of a very different order than Ford’s. While Ford’s indiscretions range from reading while driving to dealing with a conflict-of-interest hearing involving about $3,000 given to a charitable group, Katz has spent much of the autumn defending various business deals involving him, his friends, his business partners and fellow civic officials – which are all too often, according to his critics, one and the same.

In September, it was discovered that Katz had purchased a shell company, called Duddy Enterprises LLC, in Scottsdale, Ariz., from Phil Sheegl, Winnipeg’s chief administrative officer and an old buddy of the mayor, for $1.

Katz initially said he was the victim of a “witch hunt” but eventually acknowledged he had erred in making the transaction and should have bought a shell through traditional means and incurred the cost of several thousand dollars.

Within days of the Duddy Enterprises snafu, it also came to light that Winnipeg had agreed to swap a couple of aging fire halls as well as some vacant, city-owned land for some privately held property on which a new fire/paramedic station was built. That deal had been negotiated by the city’s fire chief and executives with Shindico Realty, which is run by brothers Sandy and Robert Shindleman – old friends of Katz – without the knowledge or approval of city council.

Shortly after that, Katz was defending his purchase of a $1-million home in Scottsdale from Sandy Shindleman’s sister-in-law. Katz said he didn’t have to finance it because of his successful, 40-year business career in nightclubs, travel agencies, comedy clubs and real estate: “I’ve been blessed and very fortunate in many of my business ventures. You know what? If you work hard, wonderful things can happen.”

Indeed, Katz has won three elections, thanks in large part to his ownership of the Winnipeg Goldeyes, the minor-league baseball team that won the American Association league title this year. Katz also was the driving force behind the construction of Shaw Park, the team’s downtown stadium, which can hold more than 7,000 fans.

So far, Katz has denied allegations of any impropriety, saying repeatedly that he hasn’t done anything wrong. He has launched an independent inquiry into the fire-hall land swap and taken the fire chief out of the real estate process.

There are no rules stating civic officials can’t own property in other jurisdictions. Nevertheless, Katz’s preoccupation with Arizona has drawn the ire of many. For one, Katz has missed numerous public events at which one would expect to see a mayor – such as a Remembrance Day ceremony to lay a wreath – because he was down south.

Oh, and then there’s this: thanks to the YouTube generation, a video of the mayor kicking an inner-city youth in the face during a charity soccer game a couple of years ago has received thousands of hits.

Katz had said that 2010 would be his third and last election but later recanted, saying he wouldn’t rule out running again.

However, his recent actions and the subsequent backlash from voters, both through letters to the editor and social media, may have made the decision for him.

© 2012 Investment Executive. All rights reserved.