As an early investor in the cable industry, Kilmer recognized the growing value of sports programming content in the rapidly fragmenting broadcast, cable and satellite distribution system. Research showed that sports, entertainment and leisure were growth industries in North America. Due to its immediacy and its ability to cross horizontal and vertical demographics, sports represented ever increasing value as content in a competitive distribution environment. In addition, the southern Ontario geographic region represented a large sports market. As a means of capitalizing on this trend and leveraging its construction industry expertise with respect to a need for a new arena, Kilmer initiated the NBA franchise competition in Toronto in 1992.

While initially unsuccessful in acquiring an established NBA team or new NBA franchise, Kilmer made a significant minority investment in Maple Leaf Gardens Limited in mid 1996. Using the comprehensive knowledge of modern day sports and arena economics that it had developed, Kilmer was able to demonstrate to the other shareholders of the Maple Leaf organization that significant revenue enhancement and cost saving synergies could be gained through the cross ownership of an NHL team, NBA team and a sports arena. Subsequently, Kilmer played a leading role in engineering the acquisition and financing of the Toronto Raptors basketball team and Air Canada Centre in 1998.

Subsequent to the acquisition of the Toronto Raptors and the building of the Air Canada Centre, Maple Leaf Sports & Entertainment Ltd. has realized substantial increases in revenues and operating cash flow. As well, the company has expanded its broadcasting initiatives through its two digital channels, Raptors TV and Leafs TV. More recently, MLSE was awarded a Major League Soccer franchise, the Toronto FC, and has partnered in the development of a condominium / hotel complex next to the Air Canada Centre. Kilmer has maintained its investment in MLSE and Larry Tanenbaum serves as Chairman of MLSE and as governor for the NHL, NBA, and MLS.