Iwas rather impressed to learn that Sir Jackie Stewart was one of Rolex’s original serious brand ambassadors and has been part of the brand family since… 1968, when he was 29 years old. That means the Scottish motorsports legend has been a part of the Rolex image for over 45 years, and whats more important isn’t just what Rolex has done for Jackie, but what Sir Jackie has done for Rolex.

Today, the concept of a brand ambassador (no matter the industry) is rather straight forward and typically a business transaction whereby one company wants to leverage the popularity of a particular well-known individual. It wasn’t (and to a small degree still isn’t) always that way, and people like Jackie Stewart represent an older, more involved approach, where an ambassador is really an integral part of the company in the way a consultant is. Rolex doesn’t even refer to their ambassadors by that name, but rather as “Testimonee,” as though the term were a proper noun.

That means the “Testimonee” people need to embody certain values that Rolex holds dear and in many cases they need to be existing Rolex customers. These highly acclaimed individuals bring more to the table than just a rich following of fans, but also a unique perspective that helps Rolex decide how they want to interact with a particular sport. So in this case, Sir Jackie Stewart was (and still is) quite influential in how Rolex interacts with the world of motorsports through its various partnerships and sponsorships such as Formula 1 (F1), Daytona, Pebble Beach Concours d’Elegance, the Rolex Monterey Motorsports Reunion at Laguna Seca, and more.

I was fortunate enough to spend some time with and shadow Sir Jackie Stewart in and around Pebble Beach – one of my favorite places in the world – during and around the Concours d’Elegance time in August. There is probably no one better than Jackie to be hanging out with when admiring some of the world’s most important classic cars – especially the race cars. Sir Jackie not only knows an awful lot about cars, but he has some very wise opinions on them. He is a passionate chap, and there is nothing better than being around such a talented person who can articulate what they do and don’t like. A car lover myself, I realized there was a lot to learn from someone like Mr. Stewart about automobiles, so I did by best to shut up, listen, and only ask meaningful questions.

Sir Jackie Stewart has grandchildren old enough to wear Rolex watches but the legend is sprightly and quick spoken with a charming sense of humor and a quick eye for details. Jackie’s upbringing was relatively humble, and when he was 15 years old he began working at his family’s garage as a mechanic. Fortune and effort took Jackie from being a mechanic to working for some high-profile local clients, and later to competitive skeet shooting. Jackie was almost an Olympic shooter, but fate took him down another path – car racing.

History will show that from the start, Stewart was an adept driver who used to drive a Ford van like those you can buy at this page. Jackie claims that he owes much of his professional success to his learning disability dyslexia – or at least how he managed to live with it. Stewart is remarkably open about struggling with the problem but in a sense sees his lot in life as a virtue. He is quick to name a list of noteworthy successful people who also have dyslexia and frankness about the topic is unique and refreshing. According to Jackie, dyslexia not only prevented him from finishing school, but also allowed him to hyper-focus on his strengths as a means of compensating for what he might lack elsewhere. For Jackie, his struggles with dyslexia prompted him to intently focus on certain attention-requiring tasks that require not only an extreme attention to detail, but also rapid decision making – such as shooting moving targets, or competitively driving a dangerously fast automobile.

Stewart also isn’t shy about his innate sense of competitiveness, but nevertheless is a proven team player. Car racing historians well recall Stewart’s intent advocacy for improved race car driver safety and the implementation of sport-wide rules designed to save the lives of the people he was racing with. In many ways, Sir Jackie Stewart was not only a legend on the track, winning major events such as Formula 1 three times, but also helped change the sport forever.

What you need to know about Jackie as a watch guy is that he most certainly is one. In his opinion, “Rolex is the best” – a notion he formed early in is life, and his perception has remained quite solid since buying his first Rolex in 1966, which was a Day-Date in gold on a President bracelet. He purchased it after winning a major race, and to Jackie it was his way of feeling that he “made it.” This purchase was of course prior to him working with Rolex. It goes without saying that Jackie has quite the selection of Rolex watches today after having been intimately connected with the company for so long, and he wears each of them with an impressive degree of fashionability and respect for the nature of the timepieces.