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Aiming for the Fairway: On Golf, Watches, and the Importance of Family

Author: Greg Trotter | April 30, 2024

We are shaped by our past. The experiences shared with family and friends over the years leave an indelible impression on who and what we are. The things we find interesting, the practices in which we feel compelled to engage are often influenced, in one way or another, by those around us.

For Owner Brad E., his lifelong interest in golf was shaped by his family. As he explains, “I come from a very, very, very golf-oriented family.”


It didn’t hurt that he was raised just around the corner from Medinah Country Club, one of the most storied courses in the country. Indeed, the Country Club has played host to several major tournaments, including three U.S. Open championships, two PGA championships, and the 2012 Ryder Cup.

Brad became seriously interested in golfing around the time he was eight years old. “That’s really when my passion for golf developed. I can remember when I was like eight or nine, going down to Florida to visit my grandparents in Pompano Beach. They played golf every day. I still have the scorecard from the last round I played with my grandmother.”


He began caddying at Medinah at age 12, and he didn’t quit until he turned 16. His friends began to get into the game, too. “We had a lot of fun then. All my buddies began to caddy or began to get the golf bug. We all tried out for the high school golf team.” Between friends and family, “I very much grew up around the game.”

During those years, he honed his skills and got increasingly invested in the sport. Of course, as a young kid, his strategies for practicing were not always the most professional. “I don’t know how we didn’t hurt somebody or break 1,000,000 windows! We’d go out in the side yard and hit golf balls through the neighborhood into a park that was a block-and-a-half away.”

Life and work can sometimes get in the way of our hobbies, however, and Brad’s interest in golf waxed and waned over the years. “My dad ended up joining Medinah Country Club, and that was the reason I had to stop caddying. I started doing some manual labor-type work and stopped golfing because I was so busy working.”

Inevitably, though, he found his way back. “During my senior year of college, I spent a lot of time at the driving range just kind of gathering my thoughts; that was kind of my place, you know?” But, he says, whether he’s playing or not, “golf has always been with me.”

Nevertheless, even though Brad ultimately returned to golfing on a regular basis, he’s had to change his routine up considerably. Gone are the days when he could spend most of his time out on the links.

At his peak, Brad played a whopping 150 to 170 rounds per year, but he’s had to scale that down since becoming a father to his daughter, Sophia, and son, Sully. “Now that I’ve got kids, the time away is precious.” He adds that, “Now, I’ll do 36 holes in five hours just because I don’t want to stop playing, and [I’m] jamming as much in as [I] can because I just can’t get enough of it, and I’ve got such a small window to get it.”


Fortunately for Brad, his kids are getting into the hobby, too. On this particular outing, Brad’s son tagged along for the ride. But he got an earful from his daughter when he arrived home.

“When I walked in the house, she was sitting at the dinner table, arms crossed. She said, ‘We’re golfing tomorrow.’ So the family is kind of catching the bug, too.” He adds that, “One of my daughter’s favorite things is to take her shoes off and go run on the ‘green carpet’ as she calls it.”

So, beyond the family connection and all the memories associated with the game, why is golf so important to Brad? “You know, golf is just something that you can be competitive with. When you’re on the course, you can be out there for fun and enjoyment or just to clear your mind.”


Golf is one of the oldest sports, with roots dating back to the 15th century. It’s unique, too, in that, largely, you play against yourself. Of course, in a tournament, you’re competing against others. But there’s no defense preventing you from putting your ball into the cup on the green, unless you count the rough, bunkers, wind, or other environmental factors as the opposing team. (Believe me, this might be the most effective defensive line in history!)

In addition, golf is, perhaps more than most other major sports, a mental game, something you undertake to prove something to yourself. As Brad puts it, “I’m competing with myself and kind of competing against the course.”

Like baseball, golf can be superstitious. There's lots of talk about "swing thoughts" and "repetition". It's not long before you’re wondering whether the pair of pants you were wearing when you shot a birdie on 17 are, in fact, lucky.

But Brad has learned not to take things too seriously out on the course. “I know I’m not going to the PGA…I can only control my swing. I try to control my swing to the best of my ability.” He adds with a wink, “And I’m not that great.” Brad said that, at the end of the day, “I’m out here for fun; I’m out here to have a couple of beers; I’m out here to spend time with my kids; I’m out here to hang out with my best buddies or my dad.”

If only we all could achieve such a zen-like attitude out on the course!


In fact, it seems that Brad takes a similar, relaxed approach to many different aspects of the game. When asked about his favorite golfers, for example, he didn’t reply with the usual names such as Tiger Woods or Phil Mickelson (though he did point out that Woods played a formative role in getting him and his friends interested in golf). Hero worship isn’t his style.

Instead, he gave a more measured response. “You know, not everybody needs to be Wayne Gretzky, but Wayne Gretzky needs a support staff to be Wayne Gretzky. It’s really amazing how awesome some of those people are. When you’re a kid…you only hear about the people who are scoring the goals, and you forget that somebody has to help get them there.” For him, “it’s the people who help carry the bags of the superstars” who are the real heroes.

Brad’s association with the game of golf isn’t limited just to playing or watching it, however. He’s also applied his prowess as a woodworker to crafting things like divot tools and ball markers, among other useful things.


He fell into woodworking when he learned it would be thousands of dollars less expensive to make some updates to his then-new home rather than hire a contractor to do it. Before long, he’d built a closet, some cabinets, and drawers. And, since he had the tools, he figured, why not keep going?

He began making cutting boards and various golf-related accessories. Despite a minor setback involving a saw blade and the tip of his finger, Brad has produced quite the variety of tools, including everything from ball markers to head covers, most of which he gifts to friends and family.

For him, making these objects represents the important connection he has with the people in his life. And if he gives you something, he damn well expects you to use it! 

“I want people to use my stuff. You know, I have buddies that I’ve gifted a tool to, and they’ll say ‘it’s too pretty to use.’ I’m like, no, I didn’t waste all that varnish on the tip and put seven coats of epoxy on there for you not to use it!”



Brad doesn’t put as much stock into thinking about golf gear as you might think. He still uses the same set of clubs that his dad gave him as a high school graduation gift when he's not playing with some vintage clubs. He also has a penchant for collecting custom putters from the likes of Tyson Lamb. 


Watches are a slightly different story. “I document my life with watches. I can remember on my eighth birthday sitting on the patio and opening a Dick Tracy two-way radio watch. I was always the kid with a watch.” He also fondly recalls his collection of Swatches that were always on his wrist. "I remember the Saved by the Bell Swatches. You know, the 80s watches with the clear bands that aged into that almost brownish color, and you're wondering 'what material is this'?" 

He has two Omega Seamasters that were passed down to him from his grandfather. He got a G-Shock during a trip to Hawaii in 1994, and he marked the first big deal he closed in his first job out of college by purchasing a Hamilton Khaki Field watch. His wife gave him a Tissot chronograph as a wedding gift. And he bought his first of several Oak & Oscars, a Humboldt 12-HR, when he landed his current job.

It should also be noted that Brad is one of the oddballs who does actually wear a watch when he plays golf, and more often than not, it’s either the Olmsted or Humboldt on his wrist (his Jackson sometimes makes an appearance, too).

Brad finds being an Owner to be a unique experience. As he puts it, there’s more behind the brand than just the watches themselves.


He notes that there is an obvious connection between golf and watches. After all, there are some big brands that sponsor tournaments and that can be seen on the wrists of many professional golfers. Those big brands spend big money to be omnipresent in that universe.

But that’s another reason Brad values Oak & Oscar so much. It’s organic in a way that many endorsement deals are not.

“There’s a story behind the [Oak & Oscar] brand…it’s more than just an object.” He adds that the golf community and the group of Owners he's met since buying his first Oak & Oscar are similar in that they're a great group of diverse folks. "The community helps build something that the brand can't do alone."

If there’s a single takeaway from Brad’s lifelong love of golf (or watches and woodworking, for that matter), it’s that it provides a way for him to connect with people he loves.

“It’s helped me bolster the father-son relationship, the father-daughter relationship. I can think of so many times on the golf course with my dad over time.”

From a certain perspective, our hobbies can seem silly or unimportant. But, from another perspective, the relationships they allow us to foster with others and the curiosity about the world they allow us to maintain render these activities some of the most important things of all.

Are you an Owner? Do you have a story? Of course you do! We’re always looking to meet our Owners and share their adventures on our site and with our fans. Send us a message and let us know you’d be willing to chat with us about you and your adventures, and we’ll do the rest.