WE’RE TALKIN’ DERBY… Former DXL Model reminisces on over 20 years inside Churchill Downs

What started out as a guys’ road trip from Chicago to Louisville has became an annual event for a group of men who load up their cars the first weekend of May each year and head south for the races.

Former DXL model, horse-racing aficionado and Kentucky Derby enthusiast Bill Kugelberg has attended the Run for the Roses for the last 23 years—though he missed the 2002 race due to the birth of his daughter.

“I remember at one of my first races, meeting this guy who had been coming for 20 years and thought, ‘Who the hell would come here 20 times?’ And now, here we are 23 times later…why would you do that? But it really hits you every year when the crowd starts singing ‘My Old Kentucky Home’; you really feel it – no matter what the weather is, and everyone’s singing it – that’s phenomenal,” he says.


Money was short back then, Bill was still in college, and there was no way this band of boys could secure a pricey hotel in the city for the weekend. After a few phone calls, they landed a room in a small home about a mile from the track in Louisville. The family welcomed the rowdy students in, fed them and showed them how locals celebrate the Derby…and Bill was hooked.


He remembers having to hand-write letters to ask for tickets, and weeks later, would receive a pen-and-ink letter back, along with real tickets.


He’s seen lots of celebrities: Baseball player Cal Ripken, Linda Carter a.k.a. Wonder Woman, comedian Jon Lovitz, rock star Kid Rock and countless athletes.

He’s met and has pictures and autographs from jockeys Pat Day, Jerry Bailey and Calvin Borel, winning trainer Bob Baffert, even Secretariat’s jockey, Ron Turcotte.


He even recalls finding his way into a private party held inside Churchill Downs after the races, where dignitaries would eat and drink together.

“Everyone’s dressed up…we’re in shorts…then I raise my glass and say ‘God Bless the Derby’ and everyone goes wild,” he laughs. “We snuck in three years in a row––but then they figured us out and we don’t do that anymore…when it got corporate, things tightened up––we had a good time those years.”


But it’s the horses Bill has the best memories of. “I remember my first race…Go For Gin won (that was 1994). It was pouring out and he just loved the mud,” Bill said. “Barbaro (2006) stands out to me, his trainer Michael Matz signed my glass. Then there was American Pharoah (2015 winner who went on to win the Triple Crown)…”


“Years ago we went to see Cigar, a (1995) Breeders’ Cup champion. He was at a farm in Lexington…it was like meeting Mickey Mantle,” he says.

And the wagering? Bill says it’s a hard race to pick a winner. While he watches the pre-Kentucky Derby races like the Florida Derby and Woodford Stakes to know who’s racing well, and his wife will text him her choices, it all depends on how they do on Derby day and their reaction to the crowds.

“There are about 20 horses, with six or seven that are really good. When you’re at the top of the turn, and the home stretch, some horses get spooked by the people screaming. They’re like, ‘What is this?’ It’s hard to handicap. I tend to do bigger bets on the races leading up.”

The guys always don pink attire and attend the Kentucky Oaks, a race for three-year-old thoroughbred fillies, the Friday before. The “Oaks” as it’s known, is more of a race that locals attend and has become a fundraiser for women’s health issues, primarily breast and ovarian cancer.

If Friday is about wearing pink, and betting on the fillies, Saturday is filled with a mixture of fashions…from infield to grandstand. Bill says he’s seen it all. One year, after he and his friends stood for hours in the infield, in the driving rain, he said the guys opted for more pricey seats and moved to the grandstand. They now sit about 150 yards from the finish line.

“I always hope someone (in my group) has a winner––we all hope someone wins––and if they do, they buy the next round. Sometimes we can’t see who won when they come down the stretch––now there’s a TV, but you can’t hear the announcer, it’s just that loud…it’s definitely a fun two days.”


The 142nd Run for the Roses starts at approximately 6 p.m., Saturday, May 7th. It’s one of the year’s must-see sporting events and the first race in the Triple Crown, followed by the Preakness Stakes at Pimlico Race Course in Baltimore, MD and the Belmont Stakes in Belmont Park in Elmont, NY.

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