The rise and fall of Italy’s warriors-for-hire - Stephanie Honchell Smith
At dawn on July 29th, 1364,
John Hawkwood—
an English soldier turned
contract mercenary—
led a surprise attack against an army
of sleeping Florentine mercenaries.
The enemy commander quickly awoke
and gathered his men
to launch a counterattack.
But as soon as the defending army
was ready to fight,
Hawkwood’s fighters simply turned
and walked away.
This wasn't an act of cowardice.
These mercenaries, known as condottieri,
had simply done just enough fighting
to fulfill their contracts.
And for Italy’s condottieri,
war wasn’t about glory or conquest:
it was purely about getting paid.
For much of the 14th and 15th centuries,
the condottieri dominated Italian warfare,
profiting from— and encouraging—
the region’s intense political rivalries.
The most powerful of these regions were
ruled either by wealthy representatives
of the Catholic Church
or merchants who’d grown rich
from international trade.
These rulers competed
for power and prestige
by working to attract the most talented
artists and thinkers to their courts,
leading to a cultural explosion
now known as the Italian Renaissance.
But local rivalries also played
out in military conflicts,
fought almost entirely by the condottieri.
Many of these elite mercenaries were
veterans of the Hundred Years’ War,
hailing from France and England.
When that war reached
a temporary truce in 1360,
some soldiers began pillaging
France in search of fortune.
And the riches they found
in Catholic churches
drew their raiding parties to the center
of the Church’s operations: Italy.
But here, savvy ruling merchants
saw these bandits’ arrival
as a golden opportunity.
By hiring the soldiers as mercenaries,
they could control the violence
and gain an experienced army
without the cost of outfitting
and training locals.
The mercenaries liked this deal as well,
as it offered regular income
and the ability to play these rulers
off each other for their own benefit.
Of course, these soldiers had
to be kept on a tight leash.
Rulers forced them to sign
elaborate contracts, or condotta,
a word that became synonymous
with the mercenaries themselves.
Divisions of payment, distribution
of plunder, non-compete agreements—
it was all spelled out clearly,
making war merely another
dimension of business.
Contracts specified the number of men
a commander would provide,
and the resulting armies ranged
from a few hundred to several thousand.
Individual soldiers regularly moved
between armies
in search of higher payments.
And when their contracts expired,
condottieri commanders became free agents
with no expectation of ongoing loyalty.
When John Hawkwood launched his
surprise attack
against the Florentine condottieri,
he was working for Pisa.
Later, he would fight for Florence
and many of Pisa’s other enemies.
But regardless of who was
contracting them,
the condottieri fought primarily
for themselves.
Their extensive military experience
allowed them to avoid
taking unnecessary risks
in the heat of battle.
And— while still deadly— their clashes
rarely led to crushing victories
or defeats.
Condottieri commanders wanted battles
to be inconclusive—
after all, if they established peace,
they’d put themselves out of business.
So even when one side did win,
enemy combatants were typically held
hostage and released to fight another day.
But there was nothing merciful
about these decisions.
Contracts could just as easily turn them
into ruthless killers,
as in 1377, when Hawkwood led the massacre
of a famine-stricken town
who’d tried to revolt
against the local government.
Over time, foreign condottieri were
increasingly replaced by native Italians.
For young men from humble origins,
war-for-profit offered an attractive
alternative to farming or the church.
And this new generation of condottieri
leveraged their military power
into political influence,
in some cases even founding
ruling dynasties.
However, despite cornering the market on
Italian warfare for nearly two centuries,
the condottieri only truly excelled
at engaging in just enough
close-range combat
to fulfill their contracts.
Over time, they became outclassed
by the gunpowder weaponry
of France and Spain’s
large standing armies,
as well as the naval might
of the Ottomans.
By the mid 16th century,
these state-sponsored militaries forced
all of Europe into a new era of warfare,
putting an end to the condottieri’s
conniving war games.
