Food & Drink

Meet Philly's Best Bartenders Making the Stiffest Drinks of the Year

Kyle DiRaddo and Jenna Silverman
Kyle DiRaddo and Jenna Silverman of Federal Distilling Room | Courtesy of Neff Associates
Kyle DiRaddo and Jenna Silverman of Federal Distilling Room | Courtesy of Neff Associates

Neighborhoods made for bar hopping and beers brewed with brotherly love aren’t the only reasons Philly is a great drinking city. The folks behind the bar have a lot to do with it too.

This year brought us new bar concepts and updated menus to our favorite spots, and a handful of local bartenders played a major role in further evolving and shaping the imbibing environment of our city. Here are five of our favorites of the year -- all with varying backgrounds, specialties, and ideas to bring to the Philly bar scene.

Kyle DiRaddo and Jenna Silverman

Federal Distilling Room

As a team, Kyle and Jenna go hand in hand as the front and center of Federal Distilling Room. The duo is working to make the new Kensington spot the neighborhood’s favorite cocktail lounge.

Kyle and Jenna became a bartending team in 2012, when they ended up working at the same Old City bar. Leading up to that, though, the two had different career paths: Kyle initially started bartending at Buca Di Beppo (after a little resume embellishment about his previous experience), and Jenna worked for a corporation that had her traveling around the US to train other bartenders.

After co-managing the Old City bar, the pair left with the hopes to create something with Stateside Urbancraft Vodka and to market to different brands. They have now been with Federal Distilling for two years, which both Kyle and Jenna credit as their big break in the industry. “We would not change a thing,” Jenna said.

Creating FDR’s bar program has been a rewarding experience, especially when the success of the original cocktails began to grow. For Kyle, among his favorite cocktails to make is The Daywalker: a jalapeño-infused Stateside with his own blueberry ginger syrup, with hardly any added sugar, and topped with lemonade. Jenna’s creation, The Cat’s Pajamas, is a “booze-forward” take on a martini that is equal parts dry and sweet.

Now that they've settled in at FDR, neither is in a rush for the next project. “The next thing is evolving the first thing, the Federal Distilling Room, more and more,” Jenna said. “The next tangible thing is hopefully another tasting room!”

Both Jenna and Kyle were drawn to the industry because of the community it creates. “We love meeting new people every day who are open enough to share their story with complete strangers from across the bar over a cocktail,” Kyle said. “Some of our favorite and best relationships have come out of this position. We love to work, and we are always here.”

Other than their love of work, the duo is also united in their love of Philly sports and the city itself. “Other than sports, my favorite thing about Philly is the ability to do something different every day,” Kyle said. “I love that I can get everywhere on foot if I absolutely needed to.”

Christina Rando
Courtesy of Bondfire Media

Christina Rando

Mission Taqueria

Christina has shaped an eclectic menu of creative (and affordable) drinks, including the Oaxacan Old Fashioned and the frozen watermelon cucumber margarita, at Philly’s newest and trendiest taco joint. She's also curated a mean agave spirit collection, replete with shelves full of tequilas and mezcals.

Christina got her start in the bartending world by responding to a Craigslist ad for the Apothecary Bar & Lounge, the now-defunct bar where Tiki in Midtown Village now resides. “It was a molecularly driven cocktail program that instantly had me intrigued,” she said.

After working in the music industry for five years, she returned to the restaurant world eight years ago and got her big break when she was recruited to work at the cocktail Harvard that is Franklin Mortgage & Investment Company (now The Franklin Bar) in 2010. “That bar, with all of the incredible talent it housed, was a huge game changer for me,” Christina said. “I learned and grew so much during my four-and-a-half years there."

At the Franklin, she created the Elephant Flip cocktail, a modern classic adored throughout the city by infusing rum, bourbon, amaro cocktail, pomegranate molasses, a whole egg, and Dogfish Head 90 Minute IPA. “It read like a train wreck, but tasted like a chocolate-covered raspberry,” Christina said. “I never expected something I created to be so well-received.”

At Mission, Christina is crafting a diverse and seasonal drink menu, including the jugos, which are different pressed juices. “The green juice specifically was the most difficult to get just right,” she said. “I had no previous experience with fresh juice outside the typical citrus most bars use.”

A Jersey native raised in South Philly, Christina says her favorite thing about working at Mission is creating a space where both creativity and hospitality can thrive. When she’s not at work, she’s either enjoying some tequila for herself or catching a local concert.

Aaron Deary


For Aaron, working behind the bar started early. “I was a glass lifter in my granny’s bar in Ireland,” he said. “I used to be that awkward teenager at family events, and I always felt uneasy and pressured around people, so bartending was perfect way to come out of my shell.”

When he went on to study at the University of Liverpool, he continued bartending to pick up cash, a tradition he continued when he landed in Philly four years ago. “The Irish hospitality was something that I always carried with me and still take a lot of pride in,” Aaron said. “I always had bartending jobs here and there and I realized, after almost 10 years, that it was time to just accept the fact that the industry chose me.”

Despite a long personal history in this field, Aaron still considers his current role at ROOT, pioneering the drink menu and serving hard-to-find spirits and wines to Frankford Ave, as a turning point for his career. “At ROOT I believe in the product that I am serving, which for me is very motivating and makes the job considerably easier,” he said. “I like to come up with ideas for drinks, try them, and if they’re awful, chuck them. If they’re decent, then it’s time to perfect them.”

Among his favorite drinks to make are traditional sours with egg white and variations of gin martinis, though he admits that his all-time favorite drink is just an Old Fashioned. “As cliche as that may sound, the first time I was introduced to that cocktail is when I realized cocktails went beyond frozen daiquiris and mojitos.”

Though he might be a long way from granny’s pub, Aaron sees similarities between Ireland and his new home. “Philly is a hardworking town with great people, bars, and restaurants. It’s got the tough love that we grew up with in Ireland,” he said. “Philly has welcomed my wife and I with open arms... albeit, their love for the Irish definitely helped.”

Kyle Darrow
Courtesy of Punch Media

Kyle Darrow

Red Owl Tavern

Red Owl has evolved greatly since opening four years ago, finally peaking outside of its touristy neighborhood, in part thanks to Kyle’s seasonal drinks and leadership in making his team learn the ins and outs of complex drinks.

Kyle’s first gig in bartending was at Dmitri’s, a casual place where he got to know his regulars -- and how to make cocktails properly. Sometimes, it was through trial and error, like when one customer asked him how to make a Perfect Manhattan. “I simply made a normal one and cockily responded, ‘I always make them perfect,’” Kyle said. After the customer politely corrected him on the drink’s ingredients -- the difference is equal parts dry and sweet vermouth -- he was more ready than ever to learn. “I was embarrassed by my ignorance, and that made me want to learn everything I could,” he said.

Dmitri’s became an important stepping stone for Kyle to embrace the community and creativity of the industry, as well as the freedom it provides, especially with travel. “At one point I quit all my jobs and lived in Rome for a few months, and Dmitri’s welcomed me back with open arms,” he said. Even in his current role as lead bartender at Red Owl, and with a wife and one-year-old son in tow, travel is a top priority.

“I work a lot so we can travel,” Kyle said. “My son has already been on over a dozen plane trips and out of the country twice.”

At Red Owl, Kyle wasted no time on ambitious drink menus once he took the reigns of the bar team. “My first official menu, I put out a really complicated 12-drink list. I had them crushing ice to order, making tons of egg drinks, and utilizing an unnecessary amount of bottles,” Kyle said. “I told them, if we could pull this off, we can do anything. No one on my team had more than a year of experience at that time, but they trusted me and crushed it. Literally.”

Kyle’s favorite drink to make is a Sazerac, though like many, the drink of choice for the bar team is an Old Fashioned. “I’ve also been known to make entire wedding parties layered B-52s because, sure, why not?” he said.

With all this travel experience, Kyle claims Philly is the perfect blend of everything he loves. “It’s very walkable, each neighborhood has its own distinct vibe, and the food scene is fantastic. You can spend an entire day wandering around popping in and out of bars and restaurants for a bite and a drink, and it’s affordable,” he said. “You get a sense of community you don’t get in a lot of big cities.”

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Marielle Mondon is a writer from Philadelphia. Follow her on Twitter and Instagram @MarielleMondon.