Role: Head Bartender at Calloway’s Castaways Beachside Bar & Grill

Connection: Old contact from Ray’s Jacksonville days, where both skirted the edges of the coastal gang scene.

Background:

Back in Jacksonville, Rollo ran with a loosely connected group of smugglers, fixers, and go-between guys who dealt with everything from stolen boat parts to off-the-books charters for shady clients. Ray, drifting between jobs and bad decisions, worked with them enough to earn a reputation—but not so deep that he couldn’t walk away. Rollo remembers Ray as smart, smooth-talking, and “just slippery enough to survive.”

Rollo took a hit for the crew once and did a short stint in a private lockup. When he got out, he vanished from the coast. Few knew he washed up far south and opened a bar with some buried coin and Calloway’s help—or blessing.

Current Role:

Rollo runs the bar like a ship—relaxed, but with eyes always scanning. He knows everyone’s drink, everyone’s business, and keeps just enough muscle under the counter to shut down trouble before it starts. He’s the gatekeeper to the Locals-Only Menu, and the only one who knows the real recipe for Hurricane’s Mistress.