There's a controversy as to whether Rembrandt composed Old Man with Gold Chain in Leiden, in Amsterdam, or between the two cities.

We do know that this painting dates from the year that the young Rembrandt started his fruitful business relationship and living situation with Hendrick Uylenburgh, an art dealer. In those days, the art market was strictly controlled by the guild system, which was good for artists in the sense that it gave them a direct pathway to regular employment. On the other hand, of course, the guild was a necessary barrier to the right to sell work in an area, and you could only join after serving as an apprentice for a couple of years in the workshop of a master.  Rembrandt served for four years in Uylenburgh's workshop. In his final year, he married his master's niece, Saskia Uylenburgh. Rembrandt endured this initiation process before he was admitted to the Amsterdam guild, three years after he released Old Man with Gold Chain. 

The art historian Cornelis Hofstede de Groot wrote an enormously impressive, ten-volume Catalogue raisonné based on the work of the historian John Smith—an attempt to make a systematic and definitive list of all the greatest Dutch artworks. De Groot listed Old Man with a Gold Chain as a painting of the artist's father, an opinion fully rejected by the painting's current owner. It is now accepted to be a favorite model of Rembrandt's, who appears in several of his other works. He wears here a medallion that suggests a military career, though his beret would have been considered retro at the time of its creation. The painting was, centuries later, bequeathed to the Art Institute of Chicago by Evaline M. Cone, the widow of acclaimed piano manufacturer William Wallace Kimball.

Surely, Old Man with Gold Chain emerged around the time that the master packed his bags and traversed the Haarlemmermeer, an enormous lake separating Leiden and Amsterdam. The lake received the ominous moniker "Waterwolf." The Waterwolf had a ravenous appetite for human settlements, and, in the five decades prior to Rembrandt's move to Amsterdam, it gobbled up three unsuspecting villages: Vijfhuizen, Nieuwerkerk, and Rietwijk. Some scholars say that Rembrandt commuted around or across the Waterwolf for years prior to his move to Amsterdam.