28. Cadillac Cimarron
Today, almost all the luxury brands have downsized their lineups, offering more affordable and compact versions of their big sedans. But, back in the early ’80s, this move was unheard of and hard to understand. In those days, Cadillac was suffering from an identity crisis, so they looked for a way to reinvent the company to fight all their foreign competitors. After long meetings with the product development managers, they decided to introduce a small Cadillac with a lower price to attract more customers. The problem was that Cadillac didn’t have a small platform, so they turned to Chevrolet.

They borrowed the modest Cavalier chassis, along with the small and slow four-cylinder engine. Although Cadillac dressed the Cavalier with unique trim, new colors, and a new name, the Cimarron just wasn’t enough. Sales were poor and Cadillac was under fire from their brand loyalists for ruining the company image. All throughout the industry, the Cimarron was a laughingstock. To this day, it has remained one of the worst examples of downsizing ever.