I was 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. 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.

When you see Jackie admiring the watch on his own wrist you can see tell-tale signs of a watch guy. There is a perceptive stare that takes in all the details while contemplating the gestalt of the design. His hand runs over the crystal, bezel, and bracelet admiringly. This is a watch Jackie has worn countless times, and yet it continues to impress him. At this moment, he is wearing an 18k gold GMT-Master II, but over the last few days, I’ve seen him with a Everose Cosmograph Daytona, and also a new green-dialed gold Day-Date on a matching green strap. Green is sort of his color, British racing’s color, and it happens to be Rolex’s color as well.

Jackie shares that it was difficult to select what watches to bring on this trip. He managed to narrow it down to just five, and upon returning home in the UK or Switzerland (he travels between the two) he will be eager to reunite with his collection to discover old friends. This isn’t how someone who has a mere business relationship with a brand speaks. This is a watch guy who has been fortunate enough to work closely with a company he greatly admires (any who greatly admires him) for almost five decades. Jackie loves new Rolex watches as well as the legendary models. He comments on feeling positive about the fact that a Rolex today resembles a Rolex of the past, and feels confident that a Rolex of the future wouldn’t look out of place today.

Stewart’s taste for watches is much like his taste for cars as he prefers classic, clean lines, as well as a touch of pizazz. In Jackie’s opinion it can be dangerous to be too conservative. Without a little personality, designs are easily forgotten in his opinion. It is a treat to walk around with him as he picks apart and critiques what many people consider to be some of the world’s most important automotive treasures. The man loves cars and their performance, but has a distinct eye for elegance and aesthetics. He also happens to know a great deal about the history of automobiles and the purpose of many design elements and parts that most people take for granted. Jackie can tell a car built for the American market versus the European market based on things such as the seats, and of course has an affinity for UK car brands such as Jaguar, Rolls Royce, and Land Rover (despite who may own them today).

One of Jackie’s favorite things to do is to complain about designers who dress a car in “dirty underwear.” This often repeated term is meant to characterize elements such as mirrors and bumpers, that while necessary can easily ruin the purity of a car’s design if not done “cleanly.” In Jackie’s own words, he remarks, “I like women’s underwear” (I smirk), “I just don’t like dirty underwear, you get it?” What Jackie is trying to say is that attractive underwear can augment the form of something otherwise beautiful underneath. However, if the thing meant to augment is ugly, then it quickly detracts from the object as a whole. Jackie’s tastes are quite resolutely British in that regard (classic). He likes a nicely designed car and there is no problem if is it a bit bold or creative. Having said that, if there is something about the design of a car or watch that calls too much attention to itself individually (as opposed to the whole), it is a mistake – and as an example he points to too tall roof lines or unattractive lights that simply don’t go with the greater aesthetic of the car.