In the summer of 1985, a college senior-to-be from Sheridan, Wyoming, was washing carts and lugging bags at Skokie Country Club on Chicago's North Shore.
Jim Benepe was a star on the Northwestern University golf team, and he stuck around Chicago for the summer because he needed a little money and a lot of flexibility — enough cash to eat, enough flexibility to drive to amateur tournaments on weekends.
Skokie, one of the Midwest's oldest private clubs and the site of Gene Sarazen's 1922 U.S. Open title, was closed on Mondays. That meant non-members could play the course.
At the time, a group of club regulars were growing increasingly impressed with Benepe.
"So what happens?" club member Frank Battle told the Chicago Tribune. "The day we were to get together, Jim went out and shot a 65 at Skokie, breaking the course record. After that, the sponsors were very agreeable to staying on."
The cart boy had answered the question in the only language that mattered.
When Benepe decided in 1986 to turn pro rather than grind another year as an amateur, around 25 men signed on as backers — Chicago attorneys, local businessmen, a few Skokie members and his father back in Sheridan.
Each agreed to be on call for up to $2,000 over three years, according to a July 1988 Chicago Tribune story. The pot came to around $50,000. Benepe's share of any winnings would be 75 percent. The backers' share was mostly the pleasure of being along for the ride.
"None of us got in this for the money," Battle told the Tribune. "We just wanted to help Jim get started and get some experience."
Where the money took him, first, was Asia. Then Canada. Then Australia.
"I went down there and played, and I had a good finish in the Australian Open, won the Victorian Open in the beginning of 1988," Benepe told Cowboy State Daily. "I'd already won in Canada in '87."
This success earned him an invitation to his first PGA tournament — the Beatrice Western Open in July 1988.
On the opening tee at Butler National Golf Club in Oak Brook, Illinois, he made birdie. Three days later, rounds of 71-68-69-70 put the 24-year-old at 10-under.
A closing double-bogey from Peter Jacobsen on the 18th hole sealed a one-stroke victory in the first PGA Tour event Benepe had ever entered, making him the first player since Ben Crenshaw in 1973 to win on Tour in his debut, according to Northwestern athletics.
In the clubhouse afterward, Jacobsen — a close friend of Bill Murray and a fixture on the celebrity pro-am circuit — reached for the "Caddyshack" reference sitting on the tip of every Chicago sportswriter's tongue.
"It's kind of a 'Cinderella story,' as they say," Jacobsen told the Tribune. "I don't know if he's ever been a groundskeeper, though."
The winner's check was $162,000, per the Tribune. PGA Tour exempt status ran through 1990. And a ticket to the 1989 Masters came with it.
Local Caddy
Preparing for his Masters at the azalea-clad Augusta National Golf Club, Benepe hired a caddy who already knew the place cold.
"He had started caddying there, like a lot of guys occasionally do," Benepe said. "He approached me and said, 'Hey, I worked there. I know the course. I think I could help you.' He pitched me."
The caddy — Benepe believes his first name was Robert, though the last name escapes him now — worked at Augusta year-round and caddied only selectively on tour.
"He could tell me what to do," Benepe said. Whether he could execute was another matter.
Rounds of 82 and 75 added up to 13-over 157, and Benepe missed the cut at the 1989 Masters.
"I didn't play well," Benepe said.
A second Masters invitation came in 1991, Benepe posted rounds of 78-74 and again missed the cut at Augusta.
He did manage a 35 on Augusta's infamous back-nine, before gradually moving away from pro golf and building a successful career in the aviation fuel industry. He plays about 20 rounds a year now, sometimes at the Powder Horn Golf Club in Sheridan, where he has a longstanding connection.
For this year's Masters weekend, Benepe will likely catch some of it on television, while on an end-of-season ski trip to Showdown in Montana.
Other golfers across Wyoming will likely keep their TVs locked on Masters coverage, with the birds chirping in the background and the breeze carrying the scent of magnolias across the course.
Every golfer senses The Masters is a magical experience, and some diehards from Wyoming remain determined to make a pilgrimage.
Birthday Trip
For Tom Cobb, a fifth-generation Laramie County resident, The Masters had been a fascination since he watched Jack Nicklaus execute some legendary strokes.
"I was young, and I saw Nicklaus win at 46 years old, and I think that's really when it started," Cobb said.
A gift from his wife's aunt, who knew a member at Augusta National, put Cobb on the grounds in 2011 for his 45th birthday. Walking in through the then-new entry point off the street felt, he said, like stepping through a portal.
"You come in from the street, and it's like average America — businesses, CVS pharmacy, all of this," Cobb said. "And all of a sudden you come in the back way, and you go into Augusta, and it's like a whole different world. It's like completely calm. I don't hear anything. The flowers and the smells."
Down along Amen Corner, the 13th hole became his favorite square of property on Earth. Standing in the pine straw near where Phil Mickelson hit his famous 2010 shot from the trees, Cobb stopped and listened.
"It was quiet that day, so I could hear the creek on 13 running right along that left side," Cobb said. "It was incredibly beautiful."
A practice round delivered the moment he is still telling friends about. Over on the par-3 16th, where tradition calls for players to skip balls across the pond toward the green, an eight-time major winner was giving a tutorial to a young Northern Irishman.
"Rory (McIlroy) was just a young kid — I think it was maybe his first or second year playing — and he was in a practice round with Tom Watson," Cobb recalled. "Watson is showing Rory how to execute this shot. You could tell his eyes were huge, looking at Watson do this. It was pretty fantastic."
The skip, Cobb said, came off clean. Fourteen years later, that same Northern Irishman completed the career Grand Slam at the 2025 Masters. He's back this year trying to become a repeat Masters champion.
Jackson Voice
Traveling from Jackson, Leslie Mattson made her first Augusta trip last spring, tagging her brother along for a rite she had been putting off for too long.
"If you grew up in New England like I did and now live in Wyoming for 30 years, it's usually snowing and gray, and you look at, watch TV and see The Masters, and it's green and floral," Mattson said. "If you're a golfer, you've got to do it."
Her entry into the game came in 1984 at Salem Country Club in Peabody, Massachusetts, where her father — now 92 and still playing — has been a member for more than 50 years. The U.S. Women's Open was at Salem that year, and a lifelong habit was born.
The Par 3 Contest — a Masters tradition — with players' kids caddying in miniature white jumpsuits, caught her by surprise. So did Augusta's honor code around the folding chairs patrons leave along the ropes. Walk up, she said, and you can sit in an empty chair until its owner returns.
"You just say, 'Thank you' and move on," Mattson said. "It's just this cool tradition with great etiquette and camaraderie."
Through the Jackson golf scene, Wyoming can claim a secondhand connection to The Masters through Mark Bradley, a pro at Jackson Hole Golf and Tennis. His son Keegan Bradley — from Woodstock, Vermont — is making his 10th Masters start in 2026. Also, Mark’s sister Pat is an LPGA legend.
Drawing a straight line between Wyoming golf and Augusta National requires some imagination. The places are starkly different — from the lack of pimento cheese sandwiches in Wyoming to the state’s incredibly impolite weather.
Next Dreamer
Hail, wind, snow in June — so it goes for golfers in the Rocky Mountain West.
For Teton County golfer Rob Wallace, the frustration right now is the calendar. His home courses near Jackson — Teton Pines and Shooting Star — haven't opened for the season yet. Meanwhile, the warm temps, sunny skies and profound lack of snow has golfers tapping their toes waiting for opening day.
"I think you could play on everything over here. There's no snow, but no people either,” said Wallace.
His favorite course is farther south, in the town where he grew up: the Purple Sage Golf Course in Evanston.
"Now, that's a golf course," Wallace said. The wind there can turn a Saturday round into a physics experiment.
"Heavy wind," Wallace said. "Sometimes you could throw the golf ball just right up in the air, and it'll blow a hundred yards one way or the other… a little bit of an exaggeration."
In 2024, Wallace made his own Masters pilgrimage as the guest of an Augusta National member — and came home with a ready-made Wyoming analogy.
"There's some parallels between the Masters and Frontier Days," Wallace said. "They're both rich in tradition, they're well run. The hospitality is world famous. Two iconic venues, one for rodeo and one for golf."
What stood out to him on the Augusta grounds was the discipline of the place. No phones. No photographs. Not a leaf on the fairway or a scrap of paper in the bunkers.
"It's just watching golf, which is something I think we all long for — those of us that are old enough to remember those times," Wallace said.
Off the property, Washington Road in Augusta is a different scene, crowded with pop-up vendors and tournament-week commerce, he said.
One piece of that sideshow, Wallace said, is now gone for good. A Hooters restaurant where the wild-living golfer John Daly used to post up during tournament week, signing autographs and selling merch out of the parking lot, was torn down last summer.
"It's like The Hitching Post being torn down," Wallace said, referring to the bygone hotel and political hangout in Cheyenne.
Green, hushed and scented with a bouquet of ornamental blooms, Augusta National is a world away from the Purple Sage on a windy afternoon — and a world away from Wyoming in general, as another young Wyoming pro was reminded last spring.
"Even just driving in, all the trees — it's just a different shade of green," Brendan Cobb told Cowboy State Daily. "The air feels different. I don't know why. Even when you're in Augusta proper, when you're in the town, going into Augusta National, the air just feels different. It just feels clean."
A Cheyenne Central High School product who earned all-state honors as a senior, Cobb went on to the University of Nevada—Las Vegas, for its PGA Golf Management program. He eventually earned his Class A PGA certification.
One of the perks of Class A membership came the following April: a guaranteed member's ticket to The Masters.
"That is one of the reasons why I went through the program," Cobb said. "I'm like, 'Well, it guarantees me that I get to go. I don't have to go through a lottery.'"
Cobb recalled walking through the Augusta National south gate near Amen Corner — entering a world most only watch on television.
"My first view of Augusta was the gigantic merchandise operation, these super nice bathrooms with attendants, and then just azaleas," Cobb said. "I just couldn't stop smiling. It just felt unreal."
Growing up on the dormant greens of Wyoming and, later, the stones and sand of the Nevada desert only sharpened the contrast.
A Friday walk put him within arm's reach of history in the making. On the 10th tee, he stood about three feet from McIlroy, trying to eavesdrop on a conversation between the eventual Grand Slam winner and his caddy.
"Just watching how he was kind of thinking through the tee shots. It just felt like his week, it really did," remembered Cobb.
Asked whether he'd ever heard of a Sheridan golfer named Jim Benepe, Cobb — the current assistant pro at Cheyenne Country Club — drew a blank.
"When did he play in The Masters?" Cobb asked. Told 1989 and 1991, Cobb paused. "Hey, that's awesome. He got there twice."
David Madison can be reached at david@cowboystatedaily.com.
