At the time, Mr. Rutledge said, the cable industry had an energy similar to that of Silicon Valley today, the feeling of building something revolutionary. “It was the place to be,” he said. “It was very cool. It is still cool.”

Mr. Rutledge expected to take on a major operating role in the company. But after AOL acquired Time Warner in 2001 to form AOL Time Warner, Mr. Rutledge was passed over for the chief executive job at Time Warner Cable and left the company. “I just thought I would be miserable,” he said. “They didn’t believe in the vision of the industry the way I thought it should be.”

That vision, he believed, did not involve owning networks like AOL but instead transforming the pipes that deliver entertainment and information for the digital age.

Mr. Rutledge eventually landed at Cablevision, which is controlled by the Dolan family. He helped lead the company through a period of success and the development of a series of innovations, including the introduction of triple-play bundling, in which subscribers receive a discount for purchasing multiple services including cable television, phone and Internet. The company faced challenges and lost subscribers after Mr. Rutledge left, but analysts said that it is not clear whether he was to blame.

“The open question has always been: Why did Cablevision end the way it did under his watch?” said Rich Greenfield, a media analyst at BTIG Research, adding that the company struggled in the face of stronger competition from Verizon.

Cablevision declined to make an executive available for comment for this article.

During his tenure at Cablevision, Mr. Rutledge met Mr. Malone, a larger-than-life figure who was one of the industry’s pioneers. Mr. Malone tried to recruit Mr. Rutledge to run DirecTV, the satellite operator he controlled at the time.