Goodbye to a great Raleigh bartender

That dark-eyed, bearded bartender who poured you a Hopslam at Person Street Bar last month, that guy you remember from Raleigh Times, that one you’re pretty sure used to work at the long-gone Jackpot! on Hillsborough Street – well, he’s not going to be serving you suds anymore.

That’s because stalwart downtown Raleigh barkeep Jay Winfrey has hung up his bar rag and kicked off his beer-soaked shoes for the last time.

No more shaking, no more stirring, no more listening as folks who’ve had one too many seek to unburden their souls from across a slab of varnished wood. A witness to downtown history, who watched from behind the bar as this place morphed from a sleepy capital city that rolled up the sidewalks at dusk into a destination for beer geeks and bar freaks, Winfrey is getting out of the game. He worked his final shift on Dec. 11.

“Unfortunately,” says the 46-year-old, “my age caught up with me.”

After spending his 30s and half his 40s on his feet, standing around has started to hurt.

“My feet gave out completely,” he said. “And when it came down to it, I didn’t really want to do it anymore, not after being in pain and really not enjoying it. And when you see lots of younger, just as skilled and hungrier bartenders coming up, you just have to give it up.”

Winfrey graduated from Enloe High School and N.C. State University, where he earned a degree in English. After spending a few years behind a desk working in tech and pharmaceuticals, he decided he wanted more action and embarked upon his bartending career. Wherever he tended, Winfrey sought to make himself an integral part of the place.

“The sense of ownership in a bar is what keeps any decent bartender working,” he said. “You feel like you’re making a difference and that you have a chance to help build something.”

At Jackpot!, a once-popular Hillsborough Street dive, he pitched in by attracting the attention of a playboyu.com reviewer, who wrote the place up as a College Bar of the Week. At The Raleigh Times, he was the guy ready with a pint of PBR when then-candidate Barack Obama stopped by during the 2008 primary campaign and called out, “Where’s my beer?” And for those whose tastes turned toward craft brews, Winfrey was always ready to talk shop.

“I just took my interests and ran with them and, for me, that was mostly the craft beer scene,” he said. “I could nerd out as much as I wanted to about beer and educate people.”

The emergence of the local microbrew landscape converged with his interests, or as Winfrey puts it on his LinkedIn page, he spent recent years “selling beer to ‘end users’ and assuring that our service level agreements are honored as far as enjoyment and satisfaction with product and service.” Keeping “end users” happy often translated into keeping his head when everyone else was losing theirs. His strategy for managing a bar full of drunken revelers after midnight? Keep calm and be the grown-up.

“It’s almost like being a parent or a third-grade teacher – let it be known that this is my house and you’re not going to do that,” he said. “People generally respect that.”

While parenting and bartending might require similar skills, Winfrey says he’s found that now that his stepdaughter is 11, the two pursuits aren’t necessarily compatible. He hopes the next turn in his career path offers him a way to use his degree and his creativity.

“I would love to be doing something with people,” he said. “Where I’m able to make a difference and do something good but also press the flesh.”

A few things Winfrey’s not going to miss: Making mojitos, talking to people who order Long Island Iced Teas and the pretensions of bartenders who take themselves too seriously.

“There’s plenty to learn, there’s plenty to perfect … but at the end of the day you’re just a bartender,” he said.

Cheers to that, Jay, and thanks for being better at it than you had to be.

This story was originally published January 11, 2017 at 1:05 PM with the headline "Goodbye to a great Raleigh bartender."