He later went on to establish Home Box Office (HBO) to cater to the burgeoning movie market. Dolan's entrepreneurial spirit led him to sell HBO and his cable service, allowing him to develop Cablevision, which provided television and internet services to countless households in the northeastern United States. In a landmark transaction in 2015, the Dolan family sold Cablevision to the European company Altice for close to $18 billion.

By this time, his son, James Dolan, was at the helm of what some critics referred to as the "family empire." The Dolans garnered a mixed reputation in New York, often facing public ire over the Knicks' performance and disputes with networks regarding programming, which sometimes denied customers access to major events like the Oscars and the World Series. At the time of his passing, Forbes estimated Dolan's net worth at $5.4 billion.