A Derby Hat, a Cigar, and a Smile: The Story Behind the Charleston Charlies Logo

I recently purchased a Charleston Charlies truckers cap from Ebbets Field Flannels. The cap was on sale, and I took advantage of the low price for one of my all-time favorite minor league logos—a logo featuring an anthropomorphic smiling baseball smoking a cigar. However, the infamous logo that has identified this chapter of Charleston baseball was not used from the start, but slowly emerged from a few factors.

The name Charlies was chosen by owner Robert Levine in January 1971 for two reasons: the name was short for the city of Charleston, and for his father, whose nickname was "Poor Charlie". He was a local legend who made a fortune in the junk business. Poor Charlie was known to wear a derby hat and a cigar whenever he was seen in public.

The trademark look made such an impact that the team's identity borrowed his look. The club was the Triple-A affiliate of the Pittsburgh Pirates and borrowed the same black and gold pullover jerseys for its first season. The caps were almost identical, but with a 'C' instead of a 'P'. However, a small patch on the left sleeve of some photos from the early years showed a roundel logo with

​It quickly became evident that the derby hat and cigar would be identified with the new baseball team in town. Illustrations of derby hats, cigars, and baseball were printed in local newspapers in West Virginia promoting the club, and one columnist even coined the phrase Derby Hat and Cigar Boys.

Based on numerous advertisements in local newspapers, the club’s first logo appeared in the April 4, 1971 edition of the Beckley Post-Herald & The Raleigh Register. The illustration featured a smirking baseball player smoking a cigar while leaning on a baseball bat. The player also sported a derby hat. However, a different logo appeared on the sleeves of uniforms during the first few seasons of existence.

​The derby hat was in a nod to Levin, who would attend games wearing a derby hat and chomping on a cigar. Similar advertisements would appear in the Charleston Daily Mail for Helmet and Bat Night at the ballpark.

However, a roundel logo featuring a black derby hat adorned the Pirates-style pullover jerseys, and a cigar displayed the city and team name in black script. This was more than likely the official logo of the ball club during its first year, but it does not appear in many media from that time.

The illustration was most likely created by the ball club and not by the local newspaper, as it appeared in two different papers. However, I can’t be certain of that fact, and perhaps the more familiar logo was also in production, but not used in the 1971 newspaper ads. I am sure that somebody knows this for certain and can share their expertise on the matter.

In 1972, more advertisements were published, and a new logo appeared. Gone was the traditional-looking ballplayer in favor of a giant baseball with a human body swinging a baseball bat. Yes, he had the derby hat and a stogie in his mouth. It appeared various times throughout the season, but by next year, the iconic image of the Charlies made its appearance in the local dailies.

On January 22, 1973, the classic baseball head, cigar-smoking, and derby hat-wearing logo appeared in The Charleston Daily Mail for a Warm Up ‘73: Welcome Home Fun Reception for manager Joe Morgan at the Daniel Boone Hotel. Morgan was about to lead the Charlies to 85 games and a division championship. Nevertheless, an iconic minor league logo was born.

The image was popular enough that by 1974, the Charleston Gazette-Mail published either happy or frowning faces on its front page after wins and losses. It was a simple yet effective branding piece. Back when newspapers were a vital source of information, fans could stare at the front page of the paper and see the image of the club's logo over a cup of coffee at the breakfast table.

According to Robert's obituary in 2011 in the Gazette & Mail, he created the smiley-face logo with the hat and cigar in between the seams of the baseball. In the same article, first-year player and former West Virginia State baseball coach Cal Bailey said that Robert's father was the mascot and would always be at games. It was important to take care of his dad and to make him happy. Charlie would sit in the stands at Watt Powell Park with a powered megaphone, tossing comments at the opponents and the umpire. He would always wear his hat and have a cigar in his mouth.

Sadly, he passed away in 1981 at the age of 89, and by this time, the ball club was on the verge of relocating elsewhere. The Charlies were a Cleveland Indians affiliate by this time, and attendance was dead last in the league.

The team was sold to a new group with the intent of relocation, but that didn’t happen until after the 1983 season, when the club moved to Old Orchard Beach, Maine, and rebranded as the Maine Guides. That team would move to Moosic, Pennsylvania, in 1988 and be rebranded as the Scranton-Wilkes/Barre Red Barons. The club still plays at the same ballpark and is now known as the Railriders.

Baseball returned to Charleston in the South Atlantic League in 1987. The original name was the Wheelers, but the franchise would transition to the West Virginia Power by the time the franchise moved into the brand new Appalachian Power Park (now GoMart Ballpark) in 2005. In 2009, they introduced an updated Charlies logo decked out in a pirate bandana, earring, and a derby hat. However, due to the times and health concerns, there was no cigar in his mouth.

The Power joined the independent Atlantic League in 2021 and rebranded as the Charleston Dirty Birds.  You can purchase a pepperoni roll or a canary on a cap, but not a smiling baseball with a stogie-how unfortunate.

However, the Charlies logo has been preserved for more than 50 years since its introduction. The connection between the owner’s father and his favorite headgear inspired a look that was unique and ideal for minor league baseball of that era. Heck, it would be ideal for this era of baseball, sans the stogie.

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Follow all of Marc’s stadium journeys on Twitter @ballparkhunter and his YouTube channel. Email at Marc.Viquez@stadiumjourney.com