Dolan's earliest professional endeavors focused on the packaging, marketing, and distribution of sports and industrial films, which he produced with his wife in their Cleveland home and then sold to televisions stations which syndicated the material.[7] Dolan sold his interests to Telenews in exchange for a job,[6] and when he was 26 years old, he moved to New York City and founded Teleguide Inc, a service that provided information to hotels.[8]
That same decade, Dolan founded Sterling Manhattan Cable, the first company to wire buildings to have cable television access.[8] In its early years, Sterling forged first-of-its-kind agreements to bring New York professional sports teams, cultural programming, and movies into the homes of New York City cable viewers,[9] including agreements with the New York Knicks and New York Rangers.[6] Two years later, he sold Sterling Cable's Manhattan operations to Time Inc. and renamed his Long Island business Cablevision Systems.[8]
In the early 1970s, Dolan founded Home Box Office, the first premium programming service in the cable television industry, which he sold to Time Life.[7][8] Later, he organized Cablevision Systems Corporation on Long Island[10] and spearheaded many of the company's advancements.[6] After that, he was the vision behind VOOM, Cablevision's effort to expand content delivery and meet the demands of the exploding HDTV market,[11] which was expected to include six million households by the end of 2003 and 12 million by year-end 2005, but was shut down when other directors deemed it financially unsustainable.[12]
From 2001 through early 2002, Dolan was a bidder in the sale of the Boston Red Sox. He submitted a maximum bid of $750 million,[13] but ultimately lost out to a group headed by John Henry, Tom Werner, and Larry Lucchino.[14]
The Dolan Center for Science and Technology is John Carroll University's showcase building. Completed in 2003 at a cost of over $66 million, it houses JCU's science departments, including Mathematics and Computer Science.[25]
In November 2016, Dolan received an honorary doctorate from Fairfield University, in recognition of "his remarkable contribution to [American] culture industry, for his exemplary vision and tenacity as a media pioneer, and for his important contribution to Fairfield University as a trustee and donor who has supported scholarship funds and the Charles F. Dolan School of Business."[27]
