Community wishes Wilmette’s longest serving crossing guard a happy 95th birthday

Cigarettes are dangerous, but one that made a brief Wilmette appearance in 1991 has led to a community in the decades since.

As Herb Sheriff tells it, a lit cigarette flung from a speeding convertible nearly struck him on one of his first days as a crossing guard, a job that the former engineer had yet to embrace.

Until that moment.

“I realized the kids needed somebody,” said Sheriff on March 17, a cold afternoon during his 35th year on the job — and also his 95th birthday.

Sheriff has escorted hundreds of children across Wilmette Avenue at Forest Avenue over his three-plus decades on the job, and many grateful parents showered him with gifts and praise on the special day.

Amy Senical showed her gratitude while visiting with Sheriff for several minutes. Senical told The Record that when her daughter, Greta, was in kindergarten, she would grow angry when the family had to drive her to school, “because we wouldn’t get to see Herb.”

“He’s just always been such a sweet, loving person,” Senical said. “I’m amazed he’s still working at 95 and he shows up every day and he’s really committed to the community. We all just really appreciate it.”

Resident Jeff Later placed a banner at the intersection, announcing Sheriff’s birthday and featuring a large photo of the crossing guard.

Wilmette’s Jen Manning brought Sheriff a shiny birthday headband that he kindly tried on. She also reminisced with Sheriff about the time the Village attempted to move him to another location in town. Manning said mothers nearly started a revolt to keep Sheriff right where he was. In a text thread, the mothers called themselves Herb’s Angels.

“Once I got here, the parents wouldn’t let me go,” Sheriff smiled.

Sheriff was born and raised in Brooklyn. He joined the U.S. Army and fought in Korea. Following his service, Sheriff and his wife moved to a Wilmette home, where they raised two boys and he still lives 50-plus years later.

Bad luck struck in 1990, when, at age 59, Sheriff was let go from his engineering position. Reading the newspaper, his wife came across a listing for a job in town. It was for a crossing guard, serving one of 17 or so locations through the Village of Wilmette Police Department.

In a statement to The Record, the WPD wrote: “35 years! Wow. That is an incredible milestone. What can you say about a man like Herb, who has dedicated his time, rain or shine, through freezing cold and summer heat, to ensuring the safety of the Village’s children? His commitment speaks louder than words.

“Day after day, year after year, Herb has shown up with unwavering reliability and care. His devotion is immeasurable, and his impact reaches far beyond the crosswalk, as I am sure you will find out when you ask the generations of families about his reassuring presence.”

He is Wilmette’s longest-tenured crossing guard — and has been for at least 20 years.

“I’ve been lucky. You’re lucky when you live a long time,” Sheriff said.

The crossing guard will receive more praise this spring. Wilmette’s Central Elementary School on April 22 will host a belated birthday celebration for Sheriff, complete with surprises and special guests.

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