All charm and ease as he darted through the room ego-burnishing the brightest and the best in HBO’s firmament, Plepler surely felt the tension of this high-stakes moment. He is faced with the responsibility of keeping the suits and the shareholders sated, while maintaining HBO’s creative edge as a swarm of rivals take the model it invented and threaten to beat the originators at their own game.

A few months after the Emmy party, sitting poolside at Beverly Hills’ Peninsula hotel with HBO’s programming chief, Casey Bloys, Plepler was reflecting on the panicked reaction to the idea that the network might be spoiled by corporate interference. “What happened was kind of moving,” he told me, clipping his sunglasses onto his crisp white shirt. “The response from serious people was: ‘Do not do that!’ ”

Deeply suntanned and aggressively urbane, the 60-year-old Plepler looks every bit the part of a Hollywood executive, though he’s based in New York and as likely to drop names of East Coast cognoscenti as to trade entertainment gossip. Plepler grew up in Manchester, Connecticut, the son of a trial lawyer he once described as a “Jewish Atticus Finch.” As a young man, he worked as an aide to Democratic senator Christopher Dodd, author of the Family and Medical Leave Act. After a spell as an executive on Time Warner’s corporate communications team and with HBO’s then C.E.O., Jeffrey Bewkes, Plepler was tapped in 2007 to oversee the network’s programming. Drawn to writers and journalists, he fostered a raft of political and literary projects and brought on Tina Brown, Jake Tapper, and Frank Rich as consultants. (Rich remains in the fold as executive producer of Veep and Succession.) His friendly relationship with the press helped spread his legend as a different kind of suit.

David Simon, the former Baltimore Sun reporter who has created more shows for HBO than anyone else, including The Wire and his forthcoming adaptation of Philip Roth’s The Plot Against America, likes to talk about the time he floated two very different ideas to the network. The first was a limited series based on a true story about segregation and federal housing policy in late-80s Yonkers. The second was a drama series about prostitution and the birth of the pornography industry in 1970s Manhattan. HBO may be notorious for its edgy, titillating content, but Plepler chose the former, resulting in 2015’s Show Me a Hero.

“At any other network, if you brought them the sex show, the boss jumps up and goes, ‘You got my attention!’ Whereas at HBO, the boss jumped up and went, ‘What about that political pilot?,’ ” Simon says. “It kind of made me love him more.” (Eventually, Plepler let Simon make that series about porn, The Deuce.)

As HBO’s chairman and C.E.O. since 2013, Plepler elevated Bloys to the network’s top creative job three years ago. The pair make an unlikely double act. Plepler is the showman while Bloys—a pale and youthful-looking 47-year-old—comes over as earnest, with a tendency to clasp his hands when getting a point across. Bloys spent many of his 15 years in HBO’s West Coast office shepherding comedy fare such as Veep, Girls, Ballers, Eastbound and Down, Barry, and Insecure before taking the programming reins in May 2016.

“We’re not going to say no to what we want to say yes to.”

Upon his appointment, some in the entertainment world whispered that Bloys didn’t have the experience to oversee HBO’s drama slate, which is key to the network’s future. This signature block has taken on a new urgency lately as HBO is faced with transitioning from its focus on a single night a week for its scripted shows (the big Sunday rollout) to something like the frantic output of its streaming competitors, where there’s no such thing as a schedule, just a dizzying spray of options constantly on tap.

Emilia Clarke on the set of Game of Thrones, 2016. By Helen Sloan. Thandie Newton and Jonathan Nolan on the Westworld set, 2017. By John P Johnson.

The network, which had 54 million cable subscribers at the close of 2017, already dipped a toe into the direct-to-consumer game with the four-year-old HBO Now. The app had more than seven million U.S. subscribers at the end of 2018. (Netflix had 58.4 million U.S. subscribers in the third quarter of 2018.) As viewers increasingly ditch their cable boxes, what was once a sideline is becoming the main event. To keep up, HBO will need to accelerate its output, which is why Stankey’s demand for “more hours of engagement” garnered so much alarm. His somewhat more reassuring comment that “you’re going to have to have the latitude, the freedom, and the resources to be able to go about doing what you all do very well” was less widely circulated. Of course, what HBO does well runs the gamut, from the TV equivalent of art projects to documentaries to blockbuster dramas, not all of which have the same level of payoff.