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Ben Pearson
Territory Manager – Midwest
Ben started his journey into the world of premium cigars in 2003, and in 2008 decided it was time to take it to the next level and really get involved in the cigar industry. He started working at one of his local cigar lounges and was immediately in love with the business. His obsession with all things related to premium cigars caught the attention of Jonathan Drew, and in 2012, JD brought him into the company to run the Midwest market! Ben can be found in Illinois, Wisconsin, Indiana, and Minnesota, usually with a Herrera Estelí Habano, Liga No. 9 or H99 in one hand, and a glass of natural wine in the other. When he not slinging cigars, he loves to travel, hike in the mountains out west and rollerblade at his local skatepark.
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Calvin Zimmerman
Territory Manager – Eastern Pennsylvania
Calvin started his career in cigars working at a retail store in 2015 – during this time part of his daily rotation included a Herrera Estelí Norteño Edición Limitada. After a quick stint out of the industry he knew he had to get back in. He’s been with Drew Estate since 2022 covering Eastern Pennsylvania. Outside of a lounge you can catch Calvin watching Penn State Football, playing golf, cooking in the pickleball kitchen, or cruising in a Jeep ride with the top off. His favorite cigars nowadays are Herrera Habano, Undercrown Maduro, Liga Privada T52 or Joya Clasico Medio Siglo.
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Cara Bella
Territory Manager – Pacific
Cara “DEB” Bella, known to many as Drew Estate Bella, joined the DE family in January 2016! Paving the way for many, her humble beginnings blossomed in 2008 at the 8Eightyeight Cigar Lounge in Fullerton, California. She started as a shift manager and quickly worked her way up to GM! With worlds to learn, her love for the depths of the industry grew strong as she dove deeper and deeper into the history of the industry! As she learned of the many countries that encompassed the cigar industry, and how the sun, seeds, and soils of each country created so much uniqueness, she knew she was experiencing true love! Alas, here we are many moons later! Cara oversees the management of the Pacific Territory which includes Alaska, Washington, Oregon, California, Utah and key areas of Idaho and Nevada! Many of you know, Cara is a lover of life and wants nothing more than to experience laughter with great company! Her pups ‘Merika and Liberty are her everythings! Her rotation of cigars include the HE Habano Lonsdale, M81 Corona, JDN CT, Atabey, Warped & Illusione (gasp – she’s a real cigar smoker)!
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Chris Carey
Territory Manager – South
Chris began his career in 2013 working at Mickey Blake’s cigar lounge in Connecticut and he quickly fell in love with all things cigar related. In 2015 he moved to Atlanta to take over the southeast region for Alec Bradley Cigars before moving to work with General Cigar Company. After nearly a decade as a rep he joined the Drew Estate team to take care of our incredible retailers in Tennessee, Kentucky, Northern Alabama, and Northern Mississippi. You can typically catch Chris with either a Herrera Estelí Habano or a Joya de Nicaragua classico torpedo in his hand.
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Courtney Lynch
Territory Manager – Southeast
Courtney joined Drew Estate in April of 2023. While not totally new to cigars, Drew Estate was Courtney’s official introduction to the cigar industry. Courtney’s go-to cigars are the Undercrown Maduro and Liga Privada T52. Outside of work you’ll more than likely find Courtney watching football, traveling, or grilling!
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Dave Payne
Territory Manager – Great Plains
From cigar lounges to factory floors in Nicaragua, Dave Payne – a/k/a Davey Smokes, lives and breathes the Drew Estate lifestyle. A cigar lover since 2012, he turned his passion into a career in 2019, bringing his high-energy presence and deep knowledge to every event he hosts. Whether he’s lighting up an H99, Feral Flying Pig, or Herrera Estelí Habano, Davey believes cigars are all about great experiences, great people, and great stories. If you’re looking for the ultimate cigar event, find Davey Smokes – he’ll be the one bringing the vibes, the knowledge, and, of course, the smokes.
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Ethan Sponagle
Territory Manager – Colonial
Ethan began his cigar career spending time in his family’s cigar store in Eastern PA. While working at the family store, he began his cigar journey by smoking Undercrown Shade and Joya Cabinetta. During a short stint in college, he spent time working for Cigars International’s retail team. In 2018 Ethan moved to Dallas, Texas as part of CI’s retail expansion team. During his time in Texas, he moved from Inventory Management to General Manager for the Fort Worth and Dallas regions. Ethan joined the Drew Estate team in 2022 as the Territory Manager for Maryland, DC, and Virginia. Now his go-to cigars are Herrera Habano, Liga Privada H99, and the Undercrown Dogma when he stumbles across them. When not in a cigar lounge, you won’t be able to find him anywhere, for in his free time Ethan enjoys reading, watching movies, and playing video games.
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Grace Cabezas
Territory Manager – South Florida
Grace has spent her career immersed in the cigar world, starting at Georgetown Tobacco and the Grand Havana Room in D.C. and New York before heading south to join General Cigar in Florida. She later took on the West Coast, representing Davidoff across Northern California, the Pacific Northwest, and Hawaii, mastering the nuances of diverse markets along the way. She even owned her own lounge, gaining firsthand insight into what makes a great cigar experience. Now, she’s found her perfect fit with Drew Estate, a brand that matches her passion for innovation and authenticity. For Grace, cigars aren’t just a business, they are a lifelong journey, shaped by the people, places, and stories that make this industry what it is. While she believes the best cigar is always yet to come, her go-to smokes are the Undercrown Shade Corona in the morning with a hot Cuban cafecito, her new favorite the S84 for after dinner, and on special occasions the UF-13. Don’t be shy, stop by and say hi. She’d love to hear your story.
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Jennylynn Hunter
Business Unit Manager – West
Jennylynn (JL), with over 25 years in the premium cigar industry, is a true veteran of the trade, bringing her charismatic personality, adventurous spirit, and infectious laugh that can be heard around the world to every interaction! As a seasoned sales professional she has built deep relationships throughout the industry, earning a reputation for her expertise, authenticity, and passion for the craft. As the Business Unit Manager for the West, JL and her team of Territory Managers rule the half the nation. She thrives on connecting with retailers and growing brands and delivering world-class service. Whether she’s in the humidor, at an event, or on the road, she approaches every challenge with energy and enthusiasm – because for JL, cigars aren’t just a business, they’re a way of life.
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Territory Manager – Hawaii
From the moment he first experienced the rich aroma and nuanced flavors of a finely crafted cigar, Jon Fia, a/k/a “The Cigar Mayor of Hawaii,” was captivated. His official foray into the cigar business began when he was hired as the very first employee of Xikar Accessories. Eventually, he joined Drew Estate in 2009 and has been part of the team ever since. Some of his go-to cigars are the Liga No. 9 Beli, Herrera Estelí Miami Lonsdale, and the Undercrown Maduro Corona Viva. His philosophy centers on providing not just cigars, but an experience to Hawaiian cigar enthusiasts. He invites others to join him on this journey. Whether seeking a rare, limited edition or simply looking to expand their palate, he is there to share his expertise and help them discover the perfect cigar. He encourages others to connect and celebrate the art of fine cigars together. #DE4L
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Jonathan Drew
From his home in Brooklyn to Nicaragua and back again, Jonathan held on to his dream of creating the rebirth of cigars by founding and becoming president of Drew Estate. Unwrap the layers of his journey and methods to develop the premium cigars the brand is known for.
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KD Abraham
Territory Manager – Florida
KD’s cigar journey started in 2004 while he was working on his MBA degree. KD’s extensive background in the cigar industry incorporates his early passion for the leaf, as a certified retail tobacconist. From there he joined Omerta Cigar Co., one of our trusted retail partners in Oklahoma City, where he served as General Manager. KD joined Drew Estate in 2017 and covers Florida and Alabama. His go-to cigars include Herrera Estel Habano, Joya de Nicaragua Antaño CT, and Liga Privada No. 9. When he’s not working, KD finds his way to his local iron paradise!
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Kevin McCormack
Territory Manager – New Jersey
Kevin (a/k/a K.Mack) has been with Drew Estate since 2003. He’s a married father of one who enjoys playing guitar and bass guitar in his downtime. His favorite sizes include corona gorda and lonsdale, and his current preferred blends include Blackened M81 & S84, Undercrown 10, Antaño Gran Reserva, Herrera Habano and Brazilian Maduro. Not being one who takes many self-portraits, K.Mack often posts shots of cigars only to properly showcase the vitola of the moment.
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Kyle Davis
Business Unit Manager – Central
A man who probably missed his calling to be a game show host, Kyle Davis loves to put on a show. His passion for cigars, meeting people and working a pun or joke into every other sentence makes him an ideal candidate for hosting a memorable event. Kyle has been with Drew Estate since 2016 and has plenty of stories to share with you. Be sure to catch him at his next DE Event, he would love to have a cigar with you and try to make you laugh.
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Lance Lewis
Territory Manager – Lonestar North
Lance’s background with cigars began in 2016 working retail in Dallas, Texas. Before joining Drew Estate in 2024 he served in sales roles with J Fuego Cigars, Kristoff Cigars and La Flor Dominicana. Lance covers North Texas, Oklahoma, North Louisiana and North Mississippi. Outside of work you can find Lance fishing and smoking Herrera Estelí Habano.
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Michelle Naranjo
Territory Manager – Desert West
Michelle started her career in the cigar industry in 2004 as a Cigar Broker with Hoffman Sales in Scottsdale, Arizona. She had worked with many manufacturers like Drew Estate, Rocky Patel, Miami Cigars, EPC, Alec Bradley, Dunbarton and Xikar. In 2017, she joined the Drew Estate Family as an in-house territory manager covering the Desert West, including Arizona, Colorado, New Mexico, Wyoming and Las Vegas. Throughout the years, she has built very strong relationships with her retailers, consumers, and many others in the cigar industry. She loves meeting fellow cigar smokers and introducing them to all that Drew Estate and Joya de Nicaragua has to offer. Michelle’s go-to cigars are the Tabak Negra with her coffee in the morning, and the Herrera Habano, Undercrown Shade and Joya de Nicaragua Connecticut paired with a nice glass of wine. Working in the cigar industry for 20 years has brought her so much love and appreciation for cigars and friendships that she will forever hold close. Stop by and say “Hello” at her next event.
Nick Laramie
Territory Manager – New England
Nick “Nasty” Laramie has been a Territory Manager for New England (Maine, New Hampshire, Vermont, Massachusetts, and Rhode Island) with Drew Estate since 2017. Known for his passion for the cigar industry, Nick brings a blend of expertise and enthusiasm to his role, fostering connections and elevating the Drew Estate brand across the region. Outside of his work, Nick is a proud husband to his wife, Candie and devoted dog dad to their rescue dog Coqui. In his spare time, Nick enjoys playing bass guitar, capturing moments through photography, and watching b-rated films. As a fan of cigars, Nick’s go-to blends are Herrera Estelí Habano Lonsdale, Joya de Nicaragua Numero Uno, and Undercrown Maduro Corona Viva!
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Rex Mercer
Territory Manager – Rust Belt West
Rex Mercer’s journey in the premium cigar industry started long before it became his career. As a passionate consumer, fan, and hobbyist, he spent years immersed in the culture—running a cigar club and deepening his knowledge—before stepping into the retail side of the business. It was there that he realized his passion wasn’t just a pastime, it was a calling. After gaining experience in retail, Rex transitioned into manufacturing and sales, giving him a unique perspective on the cigar world from every angle. To him, cigars are about more than just the product, they’re about the culture, the tradition, and the connections they create. That passion speaks for itself, not just in the cigars, but in the way they bring people together, strengthen communities, and forge lasting relationships. Rex can be found traveling through his territory, sharing cigars and stories, always looking to welcome both seasoned Drew Estate cigar enthusiasts and those new to Drew Estate into the fold. When he’s not on the road or in a humidor, he enjoys spending time with his friends and family or out on the range. Whether in cigars or in life, he believes in creating spaces where everyone feels welcome—because the best conversations and experiences happen when people from all walks of life come together.
Robin Hess
Retail Sales Specialist
Robin’s cigar journey began in 2017 at a local lounge, where she discovered the Deadwood Crazy Alice and instantly fell in love. True to her nature, she embraced it with enthusiasm. Her growing presence on social media soon became a source of inspiration, encouraging fellow cigar lovers to explore new favorites. In 2020, Robin’s passion caught the attention of a Manager at Drew Estate, who encouraged her to apply for a Retail Sales Specialist position covering Michigan, Ohio, and Illinois. Since then, her love for premium cigars has evolved into a full-fledged career with a mission to educate and connect with others who appreciate the craft. When she’s not at a cigar lounge, you’ll likely find Robin enjoying a fine smoke on her pontoon boat, hiking through the woods, or spending quality time with her husband and two children—always with a cigar close at hand. Some of Robin’s favorites include Blackened S84, Joya de Nicaragua Antaño Dark Corojo, and Liga Privada H99 Flying Pig.
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Ryan Rayford
National Accounts Manager
Mr. Rayford, a/k/a All The Smoke, has been with Drew Estate since 2019. His beginnings with the company were spent servicing shops in North Texas, Oklahoma, Louisiana, and Mississippi before transitioning to National Accounts in 2024. His love for cigars started in 2014, which quickly turned into managing a cigar shop by 2016. Ryan’s love and passion for old school music can be seen via social media and felt at any event he attends. He’s a proud Houston native that resides in the DFW area, so talk nice about his beloved Astros, Rockets, and Texans. His favorite Drew Estate cigars are the Herrera Estelí Habano Lonsdale, Liga Privada H99 any size, and the Numero Uno by Joya De Nicaragua. You can also catch Mr. Rayford on stage co-hosting our own Barn Smoker, Family Reunion, and Tour De Liga events across the country.
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Thomas Klebe
Territory Manager – Rust Belt East
Drew Estate Tom began enjoying premium cigars in 1997 when he began his career in television and film production. This quickly evolved into a passion and continued throughout his journey from media production to his military career, and later program management. Tom spent nine years in the military and another 15 years supporting special operations in advisory and other capacities. After hanging around a cigar lounge for some time, Tom had the opportunity to take a factory tour trip to Nicaragua and his love for cigars became even more fueled by what he saw and learned of the manufacturing process and the love the people put into the product. Shortly after that trip, Tom began working part time at a local cigar and pipe retailer and lounge in North Carolina. After several years, Tom left to live in Morocco where he took a position working for the Kingdom of Morocco. Tom later returned home and began working full-time at the local cigar lounge. After his time working in retail and as general manager, Tom started working for La Flor Dominicana as a Territory Manager covering Texas, Louisiana, Arkansas, Missouri, and Kansas. Tom moved back to Ohio to spend time with family and then began working for Drew Estate. When he is not traveling the territory representing Drew Estate, he is camping, off roading, or traveling the world.
William McPhaul
Territory Manager – Carolinas
Will McPhaul, better known as Drew Estate Turrible, made his mark in the cigar industry in 2013. He started at Anstead’s Tobacco Company, a respected local retail partner, before joining Drew Estate in 2017. Will covers North Carolina, South Carolina, the Georgia coast, Jacksonville (Florida), and St. Augustine (Florida).
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Zach Reynolds
Territory Manager – New York & Connecticut
Zach, a/k/a El Rey, has been with Drew Estate since 2015 and has been smoking cigars since 2010. He is the Territory Manager for all of New York and Connecticut. You can find him smoking something on the mellow side usually in a smaller ring gauge. If he isn’t working, he’s probably at the range smoking tee shots! His everyday go-to cigar would be the Undercrown Shade in the Corona size. Growing up in New York where Drew Estate started really means a lot to him and the culture of Drew Estate! Come out to an event near you and meet him! He’s got great stories to tell and wants to hear all about you!
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