John Hawkwood is an interesting case example. He's probably the most famous (and certainly one of the most notorious) mercenaries of the medieval period. With that in mind, we do have quite a bit of documentation of his life, albeit with significant gaps. Much of his financial information is to be found in these gaps. Hawkwood deliberately kept his finances vague and made a great show of pretending to be merely a poor, simple soldier, which is roughly equivalent to the mobsters from the Simpsons labeling themselves the Legitimate Businessman's Social Club. Certainly, much of his accumulated wealth would have gone back into recruiting, supplying, and feeding the troops under his command, for war was and has always been an extremely expensive affair. However, there's no denying that Hawkwood accumulated a pretty enormous fortune for the time.

We do know that towards the end of his career, Hawkwood was receiving pensions from several Italian cities (such as Florence) in the range of thousands of florins. But what of the vast payments he was either paid for military service or simply extorted from Italian cities? It seems that many cities had a great deal of difficulty hustling up the cash necessary to pay Hawkwood's exorbitant fees. In order to make up the difference, Hawkwood frequently took payments in estates and castles. At one point, he even owned the abbey of Sant' Alberto near Pavia. Besides castles and estates (which were often in strategic locations, allowing him to control access to important trade routes and major roads), Hawkwood bought shares in the public debt of Florence and made thousands of ducats worth of investments in Venetian businesses. He also seems to have converted much of his wealth into what his biographer William Caferro refers to as "expensive baubles." This could range from silk cloth to silver plates to chests full of rubies, diamonds, and emeralds. These riches were deposited safely for him in cities all across Italy, presumably to avoid scrutiny. Caferro notes that keeping chests full of jewelry and expensive vanity goods seems to have been the preferred mode of wealth storage for other successful mercenaries of the period as well, judging from their wills. In short, Hawkwood was as cunning an investor as he was a soldier, and maintained a fairly diverse financial portfolio. Not bad for a man who may have begun his military career as an archer!