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From allies to adversaries – the $1.4-million dispute between Michael Wekerle and veteran portfolio manager Rohit Sehgal has decades of history behind it.

As Mr. Sehgal has edged away from the limelight in recent years, Mr. Wekerle's public profile has been boosted by television appearances and a deal to purchase the storied Toronto concert venue, the El Mocambo. Despite these divergent paths, the two once had a close business relationship and friendship.

Lahore, Pakistan-born Mr. Sehgal got his start on Bay Street at an independent brokerage called Moss Lawson & Co., and then began managing money at insurer London Life Insurance Co. in the 1970s.

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He continued his ascent at Dynamic Mutual Funds Ltd., a unit of DundeeWealth at Goodman & Co., where he moved in 1998 to manage mutual funds and hedge funds. There, Mr. Sehgal won awards for savvy investing, and was one of the star managers who helped build the firm into an independent fund giant in Canada. Mr. Sehgal ascended to the role of chief investment strategist at the firm, and gained a reputation for being a man of intense work ethic, focus and conviction.

Mr. Sehgal and Mr. Wekerle worked closely together during his Dynamic years, with Mr. Sehgal buying and selling securities for his funds and Mr. Wekerle helping him find buyers for large amounts of stock as a trader at GMP Capital Inc. Mr. Wekerle once called Mr. Sehgal a "trading savant" with deep knowledge of the markets.

And long before Mr. Seghal invested in the Manhattan property at the centre of the dispute, Mr. Wekerle was one of a few close associates who had committed to a stake in Mr. Sehgal's hedge funds.

The Great Recession introduced a wave of volatility into the stock markets, and the slump in commodities added to the pain. Mr. Sehgal had been a significant investor in resources, from mining to energy. In 2008, Mr. Sehgal's Dynamic Power Hedge Fund lost more than half its value.

By late 2010, the nearly $600-million fund had found its footing and the Bank of Nova Scotia bought DundeeWealth outright, bringing big names such as Mr. Sehgal aboard. A few months later, there was also a big change for Mr. Wekerle, as he gave up running the trading desk at GMP, a firm he'd helped build from scratch.

Now in his late 60s, Mr. Sehgal left the role of Dynamic Funds chief investment strategist in May, 2013, and relinquished daily management of several mutual funds to other managers. The firm said at the time he would look out for new alternative asset-management opportunities.

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