They'll arrive under the banner of "Bikers for Trump,"
a loose confederation of motorcycle enthusiasts drawn from distinct but politically congruent factions like the "Patriot Guard Riders" and "Defenders of Liberty." For the next four days, the group will roam the streets here crowing over Trump's hostile takeover of the traditionally blue-blazered GOP and projecting high-octane support for the city's aggregated police force.
"We're anticipating a victory dance," organizer Chris Cox told CNN. "But it sounds like there's a lot of agitators and a lot of troublemakers coming to town. What happens remains to be seen, but you can definitely count on the 'Bikers for Trump' standing with the police department in the event they need it."
Over the course of a long campaign, Trump has welcomed the bikers' embrace -- and offered his in return.
"Do we love the bikers? Yes," he said during a speech at the Rolling Thunder motorcycle run
in Washington, D.C., on Memorial Day weekend. His pledges to "knock the hell out of ISIS" abroad and champion the military back home appealed mightily to a cohort dominated by veterans and retired law enforcement officers.
Derek Smith, publisher of the "Thunder Roads Ohio" magazine, said Trump's pugnacious politics make him a natural fit for the biker culture.
"One of the core things, with the hardcore, 'one percent' clubs is that they'll treat you the way you treat them, but three times back," he said. "You treat them with respect, they'll give it back to you and then some. If you treat them with disrespect or violence, they'll give it back and then some."
Cox says as many as seven in 10 of his "Bikers for Trump" have a military background. Their experience in combat, he suggests, could serve them well if the lid comes off the host city's tinderbox.
"Our first line of defense will be dialogue and diplomacy," he said on the eve of the convention. "And if that doesn't work, then we'll just have to wait and see what happens. Most bikers I know would rather have their ass kicked than their feelings hurt."
On Monday, that means providing an added layer of security to the "Citizens for Trump" rally in Settler's Landing Park, less than a mile from where Republican delegates and party poohbahs are gathering at the Quicken Loans Arena.
While Cox insists the bikers will only physically engage protesters if asked by police, he added that they will be ready at the jump "to form a meat wall" protecting Trump boosters.
But for other pro-Trump bikers in the region, the convention scene feels like a set-up. Cleveland-area biker Tommy Norton, who rode with the hardcore "Outlaws" during the 1970s, said he'll steer clear of the city, accusing federal agents of "looking for scapegoats to blame s--- on if something goes wrong."
Norton has been living "the lifestyle" since he was a teenager. In the early 1970's, after joining the military but being kept out of Vietnam because his "psychological profile said I couldn't go anywhere," he lost his hands to a motorcycle gas tank stuffed full of C-4 explosives by a rival gang.
Despite never having made it into combat himself, Norton told CNN he is "a firm believer in what (Trump) is trying to do for veterans, because it's ridiculous, they're bringing all of these immigrants in here, giving them all of these benefits, and our ex-military people are getting jacked around daily."
The real estate mogul's eagerness to rain praise on the armed forces, upset political norms, taunt critics, all while keeping a close circle of devoted aides has struck a high note with bikers like Norton.
"Most motorcycle clubs, that lifestyle is based on trust and loyalty," he said. "A lot of times on Facebook, you'll see a pack of maybe a thousand motorcycles and it'll say: We don't dial 9-1-1, we call family."
At that, Norton suggested he would reconsider his plans to stay away if bikers came under attack and appealed for aid in Cleveland.
"Think about this one," he said, offering his own parting request: "If every bike club in America got together and rode together, what kind of political power would we have?"