Bruce Simon, the third-generation owner of one of Henderson’s oldest and most iconic businesses, died Tuesday following a short illness. He had just turned 69 years old.
“It is with immense sadness and grief that we announce the loss of our beloved Bruce, who passed away on May 12, 2026,” Simon’s Shoes posted on its Facebook page Thursday morning. “We respectfully request your prayers for strength and comfort for our families and friends. We are finding it difficult to put our feelings into words.”
Simon’s Shoes had earlier posted that after sharply restricting store hours, it would remain closed until next Wednesday, May 20; it announced store hours of noon-4 p.m. that day as well as Friday, May 22, and noon-3 p.m. Saturday, May 23.
“Please understand we are very short staffed and phone calls will be difficult to answer,” the store posted May 4, the first indication of trouble but without any information concerning Simon’s situation.
Henderson Chamber of Commerce Executive Director Clay Gillham offered comments about his passing and the family store’s legacy.
“Simon’s has been a staple of Downtown Henderson for generations,” Gillham noted. “Long before I was born, my mother’s mother would make trips from Lexington to buy shoes at Simon’s because they were the only place in our state carrying the variety of sizes, styles and widths she sought.
“My first month working for the chamber, I joined a small crowd as Senator Rand Paul awarded Simon’s the Senate Small Business of the Week award for more than 100 years in business,” she continued. “It’s hard to articulate the impact of that kind of quality and consistency in the heart of our downtown, spanning so many decades. There’s really nothing that compares.
“To the Simon family and all of Bruce’s loved ones, I send my most heartfelt condolences as you navigate this tragic loss. He was a beloved member of the business community and Henderson at large and he will be deeply and sorely missed.”
Hundreds more expressions of support and prayers were posted with the store’s Facebook announcements.
“Bruce was my first Boss, I was only 15, my first job,” posted Jennifer Hanville Clary, one of a string of young students who worked at Simon’s after school and during summers over the years.
For decades, Simon’s has had a footprint that extended well beyond Downtown Henderson, with many customers traveling hours to shop its premium brands and inventory of extensive shoe sizes; as the store explains on its Facebook page, “Simon’s Shoes is a full-service fitting shoe store. We carry hard-to-find sizes for men & women.”
One second-generation Simon’s customer, referring to her and her mother, said Bruce Simon “somehow always found shoes for our long, narrow feet.”
“Bruce has been taking care of my feet for almost 40 yrs.,” posted one customer, while another expressed gratitude for “the patience extended to ‘a very hard to fit’ customer.”
One person sent “thoughts and prayers from Paducah;” another reported once seeing a Simon’s Shoes bag on the streets of Istanbul, Turkey.
One customer reported visiting the store a couple of weeks ago in sandals, and Bruce Simon suspected, correctly, that she was undergoing chemotherapy, which can cause foot and hand pain as well as cracked skin. “He spent an hour with me bringing out so many pairs of shoes to help my feet. He wasn’t selling he was helping,” she posted.
Simon’s Shoes was established by Bruce’s grandfather, Jacob W. Simon, a native of Erzvilkas, Lithuania, who emigrated to America at the end of 1909 at age 19 and joined two older brothers who had located to Henderson. When he arrived by train at Union Station, the only English he knew was a phrase that his brother Ben had told him: “Mrs. Yungbecker’s hotel,” a reference to lodging at 219 Third St. owned by Theresa Yungbecker, a German who could understand Simon, he told The Gleaner late in his life.
He was granted a peddler’s license by Henderson Fiscal Court May 25, 1911, according to a 2019 article for The Gleaner by Frank Boyett. At first, Jacob carried his wares on his back while traveling from farm to farm; rural Hendersonians were at first suspicious of the little foreigner.
But he became well-liked and trusted, and he gradually acquired a horse and buggy, expanding his reach. On Jan. 12, 1919, The Gleaner carried a story stating that Simon, who had returned from service in the Army, had purchased a half-interest in Arnold Kahn’s store at First and Main, which was “one of the oldest concerns in the city.” Simon bought out Kahn the following year.
Jacob’s son Larry joined him in the business in 1949 and by about 1960 persuaded his reluctant father to specialize in shoes, five years after the younger Simon bought the building at First and Main that his father had previously leased.
Jacob’s grandson, Bruce, joined the business in 1979, a few years after Jacob’s death on Nov. 30, 1975, and became its third owner after Larry Simon, who turned 100 last year, retired about a decade ago, though Bruce said his father regularly still called the store to check on matters.
Bruce’s mother, Lois, died in 2020 after being married to his father for 64 years.
Private services and burial will be held for Bruce Simon. Obituary information wasn’t immediately available.
However, the Simon family did offer some requests for memorial gifts: New Hope Animal Rescue , 526 Atkinson St., Henderson, KY 42420; Delta Rescue, P.O. Box 9, Glendale, CA 91209; Best Friends Animal Sanctuary, 5001 Angel Canyon Rd, Kanab, UT 84741 (bestfriends.org); or National Jewish Hospital, 1400 Jackson St.; Denver, CO 80206 (nationaljewish.org).
