Wrong, the brand hung on and is dying out with boomers. Everyone knows that the younger kids get crotch rockets. It wasn’t the hold people that ruined the brand, it was the brand marketing to Boomers for shortsighted gains. Harleys are for Boomers. Harley made sure that was the message. Now they pay for it.

charging 30k for a motorcycle didn't help

Made all the worse than the 30k motorcycle is slower and handles worse than a 13k motorcycle.

Not to mention breaking down constantly.

What did these people do to the brand image? I guess I don't understand what it was like before this happened.

Harley's were synonymous with Motorcycle Gangs (Ex: Hells Angels, etc) or with young cool men (18+).

All of a sudden in the 90's a lot of these 40-60 year olds started to try and recapture their youth or that coolness they never had. They started buying Harley's and dressing in Leather and making these ridiculous club patches and driving around revving their motorcycles everywhere. It was so cringe that you actually felt ashamed for them.

Here is a good clip from South Park that kind of sums it all up.

https://www.youtube.com/watch?v=xGyKBFCd_u4

They installed a CEO who didn't know how to ride a motorcycle but he could make tshirts move off the shelves.