ED Art Director Kevin Pennington shares three decades of bartending lessons on speed, free-pours and what it takes to turn customers into regulars for life.
(Note: This article appears in the March 2026 issue of ED Magazine.)
When it came time to find bartenders to interview for this issue’s Special Focus, we didn’t have to look far. With decades of experience behind the bar, ED’s own Art Director, Kevin Pennington, delivers hard-earned insight on what makes a great bartender, and how a job that was never meant to last turned into a 30-year career.
Like most lengthy careers behind the bar, Kevin’s started with barstool beers, a bit of inner turmoil and a proposition so outrageous it was impossible to turn down.
“I was 21, juggling a crappy job and college, questioning all of my life choices when I walked into a place called Bogart’s to grab a beer with a buddy after a softball game one night,” he recalls.
“If someone walks into the club and you already remember their name and have their drink ready, there’s zero reason for them to go anywhere else.”
— Kevin Pennington
A barback sized him up and delivered what he still considers one of the most effective recruitment pitches in hospitality history: “How would you like to make a lot of money and meet a lot of women?” Anyone who has interacted with Kevin over the years can probably guess his response: an immediate and enthusiastic “hell yeah!”
“I was barbacking the very next night,” he continues, explaining how that “next night” turned into the next three decades. “The money was too good to walk away from. I even bartended nights while working at ED, finally hanging it up about five years ago.”
Retirement, however, has been more theoretical than practical. “People still hit me up all the time to bartend the occasional private party or wedding. Apparently, you never really retire.”
During his years with Bogart’s, Kevin also spent some time working at Fantasy Nude, a Clearwater strip club he affectionately refers to as “a good old-fashioned strip joint.” A friend who purchased the club asked him to help get it up and running, which meant time spent on both the floor and behind the bar.
“I wouldn’t exactly call it an adult nightclub,” he explains. “It was more of a dive. And it was wildly unforgettable… for reasons that probably don’t belong in print.”
As ED’s Art Director, Kevin knows which stories belong on the page and which should remain in the dark, depraved corners of his mind. When it comes to bartending fundamentals, however, he’s happy to share his opinions, starting with the art of the pour. For Kevin, there’s no debating free-pour versus control-pour. Free-pour wins, every time.
“I think free-pour looks so much better than a jigger or a pour-control system,” he says. “More classy and professional. It makes the bartender look like they know what they’re doing.”
Of course, free pour only works if you’re precise. To minimize waste and keep pours consistent, Kevin suggests pour tests every other week. “Test bartenders on pouring an ounce, an ounce and a half, two ounces and three ounces, and they aren’t allowed to pour a drink until they pass.”
Beyond technique, Kevin believes the foundation of an impactful bartender comes down to three things: personality, speed and memory.
“If someone walks into the club and you already remember their name and have their drink ready, there’s zero reason for them to go anywhere else,” he says. “A great bartender doesn’t just pour drinks; they make people feel like regulars. That kind of connection keeps butts in seats and money on the bar.”
With his years of experience, it should come as no surprise that Kevin embodies the profile of a standout bartender. His ability to anticipate customer needs and build rapport made him memorable without ever resorting to flair bartending or theatrical gimmicks.
“I knew when someone needed a drink before they knew they needed one,” he continues. “I also had a rare talent: the ability to call someone an asshole (jokingly) and somehow still get tipped for it.”
Kevin may no longer sling cocktails, but his story is proof that the best bartenders don’t just pour drinks—they build customer loyalty.
As the Art Director at ED Publications for 27 years, Kevin Pennington brings ED Magazine and SE Magazine to life each month, producing artwork for both publications and their respective websites.
