“How far does your cunning reach?” he once asked his
top general. The proud reply—“I have never been
trapped in any situation from which I did not know how
to extricate myself”—set up the perfect trump card for
Muawiya, who countered: “I have never been trapped in
any situation from which I needed to extricate myself.”
Eight centuries before Niccolò Machiavelli wrote The
Prince, Muawiya was the supreme expert in the
attainment and maintenance of power, a clear-eyed
pragmatist who delighted in the art and science of
manipulation, whether by bribery, ɻattery, intelligence,
or exquisitely calculated deception. His father, Abu
Sufyan, had been the wealthiest and most powerful of
Mecca’s traders and had owned valuable estates and
mansions in the rich trading hub of Damascus long
before Muhammad had his ɹrst Quranic revelation. And
though Abu Sufyan had led the Meccan opposition to
Muhammad, his son’s family ties extended even to the
Prophet himself. After the fatah, the “opening” of Mecca
to Islam, Muhammad had brought Muawiya close in a
demonstration of unity. His eighth wife after Khadija’s
death had been Umm Habiba, Muawiya’s sister, and he
had appointed her brother to the coveted position of one
of his scribes, so that Muawiya could tell of being among
those present in Aisha’s chamber in the days that
Muhammad lay dying. If no others remembered him
being there, it was certainly not in their interest to say
so.