32 new york | july 8–21, 2019
Sumner’s expansion strategy coincided
with the ascendance of cable TV, the cresting
of MTV’s cultural power, and, soon enough,
South Park and Jon Stewart’s Daily Show.
Sumner went from local mercurial million-
aire in Filene’s Basement suits to more
famous mercurial billionaire, still, at least
for a time, in Filene’s Basement suits. He
made a risky, romantic play for Paramount
Pictures, for which Wall Street believed he
overpaid, saddling Viacom with already-
flailing Blockbuster Entertainment in a
complex move to finance the acquisition.
This made Sumner a player in Hollywood,
which he relished. The empire would later
grow to include a majority stake in CBS
(where the CEO turned Viacom president,
Mel Karmazin, once remarked to Sumner in
Shari’s presence, “I didn’t know this was
Take Your Daughter to Work Day”).
For all of Sumner’s self-mythologizing,
Wall Street talked about a “Redstone dis-
count,” meaning the cost of his whims and
his love of litigation for sport. “The problem
was that you were always afraid, if you were
a shareholder, that Sumner Redstone was
going to take the money and have a good
time with it,” explains Columbia Business
School professor Bruce Greenwald. “Buy
more crap, buy more power, whatever.”
Sumner liked to say “Content is king,” but
stock fluctuations and dealmaking were his
true fixation. “He got lucky,” says Greenwald.
“He bought companies, put them together,
pulled them apart, with no particular eco-
nomic logic. He would talk about how he
was going to manipulate the stock.”
What his daughter took from all this was
a desire for order and rules, for unexciting
words like transparency and governance
and a strong board, and she was willing to
push back at her father’s excesses. Green-
wald got to know Redstone when she was
running the family theater chain in the early
aughts, when he would invite her to speak to
his class. “She was pretty disciplined about
what she did, and she was reasonably cre-
ative,” he says. She focused on international
expansion and opening upscale movie the-
aters that served cocktails and coffee.
Sumner’s unending and—as his profile
rose in Hollywood—increasingly visible infi-
delities wound up giving Shari some lever-
age. In 1999, her mother had finally had
enough, and Sumner realized his control
could slip away if his wife combined her half
of his two-thirds ownership of National
Amusements with their children’s one-
sixth each. In that scenario, she could
have forced a sale. According to a lawsuit
Brent later filed, Sumner demanded his
children sign their voting control over to
him. Brent refused, and Sumner saw to it
that he was kicked off Viacom’s board.
The lawsuit, which accused Sumner of
favoring Shari at his expense, resulted ina $240 million settlement. Brent lives on
a ranch in Colorado.
Shari took the deal. When the divorce was
finalized in 2002, Phyllis gave up a shot at
control in exchange for half the cash from
Sumner’s holdings, which were put in a trust
that would benefit their grandchildren—
and included language to the effect that
Shari would succeed him.
By then, her kids were just about grown
and she was ready to step up her role. She
bought an apartment on the Upper East
Side in 2004, telling the New York Times
she was going to start spending more time
at Viacom. At first, Sumner bragged about
her, the better to justify his plan. “She is
obsessive,” he said in the same article. “She
is worse than I am. It is unreal. If she were
not doing the right job, she would not be
there. She was not there a year before I could
see that she was a hotshot.’’
A year later, they were openly at war.
Sumner could tolerate a nominal successor
but not someone getting in the way of his
corporate adventures. She objected when he
sought to increase his own pay and when he
used National Amusements as an engine for
his costly obsession with a video-game com-
pany known as Midway Games. It culmi-
nated in that 2007 fax to a Forbes reporter
in which Sumner railed, “It must be remem-
bered that I gave to my children their stock;
and it is I, with little or no contribution on
their part, who built these great media com-
panies.” The whiplash could be severe. At
a media conference a few months later,
when asked what he wanted his legacy to be,
Sumner replied unironically, “I guess I’d liketo be known as a loving and supportive
father and grandfather.”
By the end of 2008, the bursting of the
financial bubble was grim vindication for
Shari; overloaded with debt, National
Amusements was forced to sell the video-
game company, into which Sumner had
invested hundreds of millions of dollars, for
$100,000. It was Shari’s breaking point. She
threatened to sue her father for mismanage-
ment and mistreatment, even drafting a
complaint, but unlike legions of Redstones
who’d sued each other in public court, she
made a deal that kept the details of the dis-
pute private. On paper, she was slated to
take over the empire, but distanced herself
from day-to-day operations and hung out a
shingle on her own. In 2011, she founded a
venture-capital firm, Advancit Capital, with
her daughter’s husband, Jason Ostheimer.
(Once again, a Redstone was going into
business with the son-in-law and not the
daughter.) Her father had always embraced
the future, and she wanted to do that too,
investing early in the podcast company
Wondery and the meditation app Head-
space, which she uses herself. Two of the
heads of the companies she has invested in
told me she keeps in close touch, texting
them ideas and inviting them to Patriots
games. It was a world without her father
and one where people wanted her around.left to his own devices, Sumner
entered what might charitably be called his
baroque period. He married a school-
teacher half his age and moved into a Medi-
terranean mansion in a gated community
in Beverly Hills with an indoor aquarium
and a pool in which Sumner would swim
naked daily. The couple bragged to friends
about how much sex they had. After they
split, Sumner took up with Sydney Hol-
land, 47 years his junior, after having been
introduced to her by Millionaire Match-
maker Patti Stanger in the fall of 2010. A
year later, Holland moved in, eating lunch
and dinner with Sumner seven days a week
and planning Sunday movie night with
friends like Charlie Rose.
At first, Shari tolerated Holland. She was
biding her time, throwing herself into the
tech world in preparation for what she
assumed would be her ascension. But her
father’s fidelity was ever wavering, and she
found herself again competing for the
throne, this time with Viacom chief execu-
tive Philippe Dauman. “I can’t say what will
happen after I’m gone—which will be never,”
Sumner told the Times in September 2012.
“But everyone understands, I think, that
Philippe will be my successor.” Two weeks
later, he gave an interview saying no deci-
sion had been made.
Worse for Shari, her already strained“If my father wants me to
drop dead, he doesn’t need
to do anything else.
He has made how he feels about
me perfectly clear.”