Preakness Dearing
Tommy Ennis does some work during his last year painting the weather vane in 1986 at Pimlico.

This year being in almost every way a departure from the norm in the sporting world, Tom Dearing spent his Saturday evening proofing some work for his job as a King's Daughters Medical Center spokesman, he said.

Most years, at 6:48 p.m. on the third Saturday in May, Dearing is glued to NBC as that rare bird — the Kentucky resident more interested in the Preakness Stakes than the Kentucky Derby, and not just to see if there's any chance at a Triple Crown.

Dearing has a personal connection to the Preakness. That race may not be able to match the Derby in pageantry, but it has one signature tradition: immediately following the event, the colors of the winning horse's jockey are painted on a weather vane which sits high above the winner's circle at Pimlico Race Course in Baltimore.

During Dearing's childhood, his grandfather was the painter on display.

Tommy Ennis, a sign painter in Charles Town, West Virginia, and the namesake of his grandson, manned that prestigious duty for 26 years, according to the South Florida Sun-Sentinel. His last trip up that ladder was in 1986, when Dearing was 16.

Frequently, Dearing and other family members would accompany Ennis and get into the Preakness free of charge.

"I really didn't even appreciate most of it because I was too young," Dearing said, "but I just knew most every year we would go down and see these horses race, and Grandpa got up on this thing and painted, and he was on TV for a couple minutes once a year."

One year — Dearing thinks it was 1982 or '83 — he got to help his grandfather. As Dearing tells it, because of rain, Ennis's assistant didn't think he would be needed to hold the ladder, so he headed for the Pimlico infield and a good time.

"People get pickled beyond belief," Dearing said of that scene. "I was always amazed that my parents let us walk over there, because we'd walk under the track, and there was just all kinds of ...

"There were some decent musical acts, but there was just stuff that no preteen kid should see," Dearing continued after a pause, cracking up in recollection.

Ennis's assistant was thus unavailable for work involving steady hands and heights when the rain cleared off and the race was run, so Dearing, aged 12 or 13, stepped in in his stead.

Dearing remembers encounters with ABC sportscasters Howard Cosell — who was "sitting there in the middle (of the clubhouse) and didn't move a muscle ... he just sat there with his legs crossed and we had to work our way around him" and Jim McKay, "who was much nicer and had one of the yellow ABC jackets on."

Dearing also took note that his grandfather "painted without a drop cloth and never spilled. I don't know how he did that, but he was just a really, really good painter."

Ennis died in 1993. By then, Dearing, a native of Inwood, West Virginia, was in the Tri-State. He'd "wanted to go to journalism school and hated WVU," Dearing said with a laugh, so he attended Marshall.

During that time Dearing realized he didn't want to work at a newspaper, so he ended up on a public relations track. During the summer between his junior and senior years in Huntington, he applied for an internship at KDMC — which at the time Dearing had never heard of, he said. When the hospital had a job opening a couple of years later, he returned and has been there ever since.

Dearing was reminded of his grandfather's annual excursion last year. Scrolling through Facebook, Dearing encountered a black-and-white photo of Ennis painting that he had never seen on the Preakness's page.

"I was like, 'holy cow, there's my granddad,'" Dearing said.

Dearing's aunt, father and cousins had never seen the photo before either. He obtained the original photo through the Preakness's page. When it popped up again in his Facebook memories a couple of weeks ago, it was a reminder of a hope that, though the Preakness wasn't run on Saturday, having been postponed until Oct. 3 due to the COVID-19 pandemic, eventually some semblance of normalcy will return.

"It'll come back," Dearing said. "I miss it, but it's nice to look back and do some research and see all the times that we got to go to the race. It was a time before people really were on TV."

Except for his grandfather, for three minutes a year.


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