The Cadillac Escalade has a few different factors working against it when it comes to preserving resale values, and it is telling that the drop in sales over the past several years did not drive up the demand for used models as it did with several other models of cars. The Escalade was always the natural evolutionary peak of the Nineties SUV trend, and there was never any question that Cadillac would be able to make money off of it. And for a time, it was the most interesting thing about Cadillac.
While you could very much say that the Escalade was the product of the times when it was introduced in 1998, it did also have an older spiritual ancestor. This was the 1975-76 Cadillac Mirage, built in very small numbers by a third-party coachbuilder. It was a time when the Chevy El Camino and Ford Ranchero were still enjoying success. So a custom-bodied pickup version of the Eldorado was sold through select dealerships, and somewhere between 200 and 250 units were sold. Nobody was willing to commit to the gamble of a big production run for such a weird niche vehicle, but this caution is understandable.
Although luxury versions of utilitarian vehicles sometimes work, it has to be under the right circumstances. Just such circumstances existed when the Escalade was introduced in 1998 for the 1999 model year. The SUV trend was by this point in full swing, and with no end yet in sight. Everyone seemed to want an SUV at this time, and since nobody was taking them off-road anyway, there was a growing luxury SUV market. A newly redesigned Range Rover had just hit the market a couple years before, and luxury brands everywhere were scrambling to bring out something to offer. Even Lincoln would end up beating Cadillac to the punch with its new Navigator, which had become an instant success.
It had taken just 10 months to go from a green light from the company brass for Escalade production to begin. This rush showed in the finished product, as the first generation was one of the world's finest examples of badge engineering ever. From the outside, these badges serve as the only indicator that you are looking at the Cadillac and not a GMC Yukon Denali. The interior was basically the same as well, but that didn't keep people from buying them. But the first model didn't last long, and the redesigned version, which looks much more like its own model, sold considerably better.
The second generation was also when Cadillac introduced the EXT, with its pickup bed in the back. This was pretty obviously a Chevy Avalanche with some extra chrome bits glued to it, and has always been the slowest-selling of all Escalade types. Although it did absolutely destroy the Lincoln Blackwood pickup in sales. The third generation of the Escalade, which debuted 2007, probably should have been the most popular yet. But by this point, the SUV trend was on the decline, and both it and the Escalade took another big hit with the global financial crisis.
New sales of most vehicle models have improved in the past few years, but the Escalade continues to decline. Plans are being made for a new generation, which could solve these problems, but as it stands, the big Caddy is unappealing to consumers as both a new and a used model. Part of the problem with resale value is simple: it is the most stolen vehicle in America. That will make anyone nervous, but it tends to be a bigger issue for used buyers. But the big issue seems to be the same one that keeps the Escalade from being a hit when new: it is a huge symbol of excess, and in the current climate, such outlandish exuberance have become extremely unfashionable.