Indian Chief Dark Horse

"The most resolved American V-twin you can buy used right now."

The Chief Dark Horse is a proper bruiser — that 116ci Thunder Stroke motor pulls hard from basically nothing and sounds genuinely menacing with even a mild exhaust swap. Ride one and you understand immediately why people choose Indian over Milwaukee iron. The chassis is tighter, the brakes are more confidence-inspiring, and the whole package feels more resolved than comparable Harleys from the same era. Used examples from 2016-2022 are plentiful and often well-specced by previous owners who spent big on accessories. That said, go in with eyes open. Check the rear cylinder heat management carefully — these motors run hot in traffic and some early owners cooked seals. Electronics on pre-2019 models are rudimentary, so don't expect much rider aids. Parts availability is improving but still trails Harley's ecosystem significantly. Budget for a comfort seat within the first year because the stock unit punishes anything over two hours. Pull the service history hard and inspect front fork seals — they're a known weak point on higher-mileage bikes.