Those familiar with El Greco's portraits from this period will be entirely familiar with the style of Portrait of a Gentleman (1600-1605). The artist would normally use dark, neutral backgrounds and put his subjects within black clothing, which was popular at that time. Normally, it would be the white ruff and cuffs which would then contrast against the darkness, and we see that again here. The ruff used here is particularly large, with two levels helping it to grab our attention. The gentleman's face is almost lost within this touch of flamboyance and extravagance. One can immediately assume this model to be of significance within his local community, in order to wear clothing in such a manner. El Greco allowed a number of different subjects to sit for him, though they would always be of a high status as otherwise there would be no funds to pay for the painting. He would know some of the subjects, whilst others would seek out the artist specifically to obtain their own portrait. El Greco would try to fit these commissions between larger projects, as a means to building his reputation and also providing regular income to himself and his studio.

The model within this painting has never been formally identified, though several suggestions have been put forward by those familiar with his career. The likes of Miguel de Cervantes have been put forward as possibly the man in this painting, alongside others who were in and around the artist's circle, but it would be impossible to be sure today. This is the case for a number of his portraits, where documentation has been lost in the centuries that have passed since. There would also be a cross over in this period of his career, where the artist's studio would also become more prominent and this would lead to further confusion as to who was involved with what painting. Many copies were also produced and sold around Spain, without the levels of documentation that appeared in later centuries. Portrait of a Gentleman remains on display at the Prado Museum, as one of over forty artworks from his career that are to be found here. He was popular with some Spanish monarchs, who would later gift their collections to this important Spanish museum.

He would become a highly regarded portrait painter, with this piece alone being considered of a high technical standard. Patrons started to be drawn to the artist, even though some in Spain saw him as an outsider because of his roots in Crete, and his time living in Italy. El Greco was a strong character who was willing to accept conflict, so long as his lived proved successful and he also fiercely defended the unusually expressive nature of his work. Something that did bring favour within Spain was his clear commitment to God, giving his religious scenes a particular authenticity. It was rare for an artist to profit from their work during their own lifetime, but El Greco was able to forge a successful career in which his legacy was already understood, long before historians of the 19th century would start to laud his work all across Europe. This success was matched by the desires of some Spanish monarchs to acquire his work for their own personal collections.