Bob Guendelsberger's keepsake from an unexpected and unrepeatable 1968 high school sports victory is a pair of dirty cream and brown Puma running shoes enclosed in a glass-topped, wooden box.

The gold-plated engraving on the front boasts: "Shoes that beat Bruce Jenner.''

Even without the shoes, though, it is unlikely the 60-year-old New Milford lawyer and Town Council member would forget the unforgettable -- beating the world-famous 1976 Summer Olympics decathlon champion in the pole vault.

It was a spring day in Guendelsberger's senior year at New Milford High School. The Green Wave was playing host to Newtown High School in a dual track and field meet at the Sunny Valley Road school, now the Sarah Noble Intermediate School.

Guendelsberger was all set to compete against Newtown High's new sports star, Bruce Jenner, a junior transfer from Sleepy Hollow High School in Tarrytown, N.Y.

Their first event as competitors was in the half-mile relay race.

"I was New Milford's lead-off and he was their lead-off. I was running as fast as I could; my stomach was burning,'' Guendelsberger recalled.

Suddenly, he heard a whistling sound at his side. A moment later, he saw the soles of Jenner's shoes.

"He passed by me like I was standing still,'' said Guendelsberger, who recalled how Jenner always wore a Sleepy Hollow High sweatshirt even though he was competing for Newtown. "He blew right by me ... I was (peeved).''

Aware of Jenner's athletic prowess from playing football against him, Guendelsberger said even then, he marveled at Jenner's muscular physique and movie-star good looks, not to mention, his extraordinary speed and agility.

"He was big -- broad shoulders, strong, muscular. Whether he was playing football, basketball or track, this guy was just a really good athlete," Guendelsberger said. "He was the guy to beat.''

On New Milford's track team, Guendelsberger was groomed as a pole vaulter, his acumen enabling him to earn an athletic scholarship to Alfred University in New York. He even went so far as to spend $85 -- a hefty price tag at the time -- to buy his own fiberglass pole.

Still, Guendelsberger said he had no illusions that he might outperform Jenner, who was well-known for his pole-vaulting expertise.

But on this day, the fates aligned in Guendelsberger's favor.

As the pole vault started, Jenner took a first jump at a modest height -- under 10 feet, Guendelsberger recalled.

But on his descent, Jenner sprained his ankle and failed to clear the bar. He was out of the contest, but according to the rules, he was still considered a competitor because he had made an attempt.

Guendelsberger, whose own ankle was taped after spraining it the day before, followed Jenner with a jump of over 10 feet.

"So I beat Bruce Jenner,'' said Guendelsberger, who gave up pole vaulting when he went to law school in Ohio.

No matter that it was something of a fluke, he grinned with a comical swagger.

"A win's a win, baby,'' Guendelsberger boasted. "Could I have done it again? Probably not. Doesn't matter, though. It goes down in the record books as a win. It earned me bragging rights.''

One of Guendelsberger's four grown daughters, Kaitlin, the office manager in the family law office on Route 202, said she and her sisters are still amazed at the feat.

When she was younger and unaware of the story, Kaitlin said she always wondered why her father would keep "a pair of stinky shoes.''

Of course, Jenner did not earn the title of the world's greatest athlete until 1976, when he won the Olympic decathlon with a world record point total.

And yet, Guendelsberger said it was clear even then that Jenner was no average high school athlete.

Everyone, including Jenner, who was undoubtedly aware of his physical talents, expected he would make a name for himself in the sports world someday, Guendelsberger said.

But no one might've guessed Jenner would one day become a household name and land on the front of a Wheaties box.

For Guendelsberger, it was obvious Jenner had a gift.

What was Jenner's reaction when Guendelsberger pulled off the pole vault win?

"I doubt it phased him one way or the other,'' Guendelsberger said.

These days, Jenner is famous for being the Kardashian sisters' stepfather in their reality TV show, "Keeping up with the Kardashians."

Guendelsberger, meanwhile, stays busy with his civic pursuits in New Milford. He is also an avid recreational skier.

Guendelsberger insists he has no envy for Jenner's lifestyle, nor would he ever undergo a facelift. He also said he's never watched Jenner and the Kardashians on TV.

But Guendelsberger will always relish the day he beat Bruce Jenner in the pole vault.

"If I had cultivated my body rather than my brain, maybe I'd be on a (Wheaties) box -- NOT!'' Guendelsberger chortled.

Contact Nanci G. Hutson at or at 860-354-2274.