In his 2001 autobiography, ‘A Passion to Win’, longtime Viacom boss Sumner Redstone uses the word “friend” 67 times. That’s not counting mentions of “friendship” and “friendly”.

Who are these friends? Mainly people Redstone had worked with or done deals with. Since Aaron Spelling’s TV production company ended up as part of Viacom, Redstone writes, “he has become one of my closest friends”.

Redstone and his fellow top executives at Viacom “are not just business associates, we are friends.” His assistant, Tilly Berman, is “a close friend not only of me but of my entire family.” Cablevision founder Chuck Dolan is “an admired friend”.

Former Time Warner CEO Gerald Levin is “a very close friend”. Redstone and former Nickelodeon chief Geraldine Laybourne are “extremely close friends”.

I could go on and on: Others name-checked as Friends of Sumner include Hillary and Bill Clinton, Archibald Cox, Martin Davis, Marvin Davis, Ted Kennedy, Sherry Lansing, Jack Valenti, Barbara Walters — and many more.

But let’s focus on a couple of friends who happen to be in the news. Philippe Dauman, the current CEO of Viacom and a long-time Redstone lieutenant, is a “close friend”. Redstone’s children Shari and Brent, meanwhile, “are my best friends”.

This would seem to give Shari Redstone an edge over Dauman in the current battle over the now-92-year-old Sumner Redstone’s fortune. “Best” is better than “close”, right?

Things are never quite that simple with Sumner Redstone, though. Five years after the elder Redstone wrote that his kids were his “best friends”, Brent Redstone sued his father, then ended up selling him his stake in the family company. In 2014, Sumner reportedly made a similar offer to buy out Shari, their relationship having deteriorated so far that for a time they communicated only by fax.

Shari turned that down, and eventually started talking to her dad again. Now Dauman, who stayed loyal to Redstone even after being pushed out at Viacom in the 1999 merger with CBS (he returned in 2006 after the two companies split again), is suing to prevent his removal from the family trust.

It’s anybody’s guess what will happen next. “Friend” doesn’t seem to mean quite the same thing to Redstone as it does to most of us. In a 2001 “New Yorker” review of the billionaire’s book, Malcolm Gladwell concluded: “Redstone aligns his passions with his interests, and when his interests change, so do his friendships.”

Consider his relationship with his fellow media mogul Barry Diller. For a long time, Redstone writes, the two were “extremely friendly”. As they battled each other for control of Paramount in the early 1990s, Redstone began to have doubts (“Barry was supposed to be my friend”). After Viacom won that bidding war, but at a cost $2 billion higher than originally anticipated, he spent several years referring to Diller as his “$2 billion ex-friend”.

But in his autobiography, he concludes, “I once again consider Barry a good friend.”

In a business context, this flexibility was quite effective. Redstone got along well with lots of people. If they let him down, or went to war with him, the friendship faded.

But he wasn’t averse to rekindling it later, if it was useful. In any case, he allowed neither friendship nor animosity to stand in the way of his main goal — which was, as the book title says, winning.

From his high school years at Boston Latin (where he had, he reports, the highest grade point average in the school’s 300-year history) through two quick years at Harvard through breaking Japanese codes during the Second World War through law school at Georgetown and then Harvard (where an unwarranted D from an alcoholic professor — not a friend — doomed his chances of graduating No. 1 in his class, something he was still steamed about half a century later) through a short but spectacularly successful legal career to joining his father’s drive-in movie company and building it into an entertainment-industry giant, Redstone was always focused on coming in first.

He writes: “Most people who succeed in significant areas do not succeed because of a desire for money. There are other more important motivations: the desire to be the best and the desire to win. And for better or worse, the desire for power. Winning is power.”

This candour is refreshing. And there are even a few parts of the book where Redstone’s passion for winning is infectious — notably the account of his 1986 hostile takeover of Viacom, which is when he got to know Dauman, then a hard-working young associate at the law firm that represented Redstone.

After a while Redstone’s life story does start to feel a bit empty, though. “Redstone is a supremely unselfconscious man,” Gladwell wrote in his review, “and that trait, which has served him so well in the business world, is fatal in an author.” The unexamined life may or not be worth living, but it’s definitely not much fun to read about.

It can also get terribly sad at the end, when there’s nothing left to win. After decades of accomplishment and excitement, Redstone’s waning years have been embarrassing, even a little tragic. Mainly it’s because, despite his self-proclaimed gift for friendship, he doesn’t seem to have any real friends.

— Washington Post