Stuart Handler

Chief Executive Officer, TLC Management

Handler’s multifamily firm is best known for amassing and operating large portfolios of vintage apartment buildings. Since launching TLC in 1997, Handler has built one of the region’s larger privately held apartment platforms, historically concentrated along the lakefront and on the North Side.

That long-hold strategy has evolved in recent years. In 2025, Handler emerged as an aggressive suburban buyer, paying roughly $60 million for apartments in Mount Prospect, and following that with a $100 million acquisition of a large Vernon Hills complex. The moves reflected both rising competition in the city and Handler’s belief that well-located suburban rentals offered better pricing and fewer political landmines.

At the same time, TLC has shown a willingness to prune. Later in 2025, Handler sold a portfolio of Hyde Park apartment buildings, one of the firm’s more established Chicago holdings, signaling a tactical shift rather than a philosophical one. TLC remains committed to long-term ownership, but the sales underscored the reality that recycling capital has become harder to avoid as values, taxes and compliance costs climb.

Handler has been outspoken about the pressures facing multifamily owners, particularly rising assessments and regulatory uncertainty. He has supported a change in the Cook County Assessor’s Office from two-term incumbent Fritz Kaegi, who many multifamily investors have said is creating unpredictable costs that ultimately constrain investment.

— Sam Lounsberry