Khamenei is a geriatric cleric ruling
over an increasingly secular population
whose median age is 30. Aside from Syria’s
Bashar Assad, he has no reliable friends in
the world. And he goes to bed every night
and wakes every morning believing that
the U.S. government is actively trying to
overthrow him. This paranoia— frequently
reflected in official state media, which
Khamenei controls—is also driven by po-
litical expediency. Mohammed Khatami,
the reformist cleric who was Iran’s Pres-
ident for two terms (1997–2005), told
me in a private meeting in Oslo in 2008
that when he was in office Khamenei
used to tell him that Iran “needs enmity
with the United States. The revolution
needs enmity with the United States.”
Despite its distance and a military bud-
get less than 3% of that of the U.S., Iran
has loomed large in American domestic
politics. The Iran hostage crisis ended
Jimmy Carter’s presidency; Iran- contra
tainted Ronald Reagan’s presidency; Ira-
nian machinations in post-Saddam Iraq
exhausted George W. Bush’s presidency.
And the Iran nuclear program and nego-
tiations engrossed the Obama presidency.
Trump inherited from Obama an Iran
that resembled the late-stage USSR, pow-
erful beyond its borders but hemorrhag-
ing billions of dollars in foreign entangle-
ments and mired by internal economic
malaise and ideological fatigue. But in-
stead of marshaling global unity against
Tehran’s malign activities, Trump aban-
doned the nuclear agreement the U.N. re-
ported Iran had been adhering to.
To this day, senior U.S. government of-
ficials confuse Khamenei with his char-
ismatic predecessor: Grand Ayatollah
Ruhollah Khomeini, the founder of the
Islamic Republic. Although Khomeini
died 30 years ago, his sinister daily pres-
ence on American TV sets through the
444-day hostage crisis left a lasting im-
pression. “These economic sanctions are
just a part of the U.S. government’s total
effort to change the behavior of the Aya-
tollah Khomeini,” Secretary of State Mike
Pompeo said in a November 2018 briefing.
“The assets of Ayatollah Khomeini and his
office,” President Trump followed up in
June 2019, “will not be spared from the
sanctions.”
The confusion—like so much the U.S.
does—may serve Khamenei. He prefers to
obscure his vast power behind the Islamic
Republic’s byzantine array of institutions.
The Assembly of Experts, Guardian Coun-
cil, Expediency Council and Revolution-
ary Guards evoke a Game of Thrones–style
drama. But in reality they are all led by
individuals handpicked by Khamenei orunfailingly loyal to him. They serve to but-
tress rather than check his authority.
Khamenei is a reader. He has fre-
quently said Victor Hugo’s Les Misérables
is the greatest novel ever written, and his
Instagram feed shows him smiling as he
reads a Persian translation of Fire and
Fur y, Michael Wolff ’s unflattering ac-
count of Trump’s first year in office. And
though it’s unknown whether he’s read
The Prince, he displays a Machiavellian
genius in manipulating what Iranians call
“the system.” Khamenei’s slyest feat: as-
suring that he has power without account-
ability, while Iran’s elected Presidents
have accountability without power.
Iran makes a great show of its highly
manipulated presidential elections, and
their importance to the public became
clear when the 2009 ballot was stolen.
Millions took to the streets in what be-
came known as the Green Movement, bru-
tally quashed by the leader’s internal mi-
litia, the Basij. Marring the ballot was a
dangerous miscalculation by Khamenei,
and perhaps an unnecessary one. No mat-
ter the challenge brought by a President—
the economic challenge of Hashemi Raf-
sanjani (1989–1997), the democratic
challenge of Khatami, the populist chal-
lenge of Mahmoud Ahmadinejad (2005–
2013) or the pragmatic one of Rouhani