The term “windshield cowboy” is used to refer to a rancher who prefers to drive, rather than riding. As a general rule, it is used in a derogatory way, implying that the rancher is a pretender, rather than an actual working rancher, and suggesting that he or she may not even be able to ride. The term appears to date to the early 1970s, although it may be older, and it was popularized during the presidency of George Bush, who was often accused of being a windshield cowboy.
Most working ranches do, in fact, use trucks for an assortment of tasks, including working animals, especially at remote locations. However, ranchers and cowboys also use horses, and tend to be skilled riders, because there are numerous tasks for which a horse is far more suitable than a vehicle. A cowboy who doesn't ride a horse seems a bit out of place in Western culture, and tends to be viewed with suspicion by fellow ranch workers; after all, it's been said that “the best thing for the inside of a man is the outside of a horse.”
Someone who purchases a ranch as a novelty, with the intent of using it as a vacation home rather than actually working the land, may often be accused of being a windshield cowboy. Many Westerners are dismayed to see ranches transformed from vibrant working communities into vacation spots used infrequently by their owners, and the commodification of ranches has caused the cost of actual ranching to rise, creating further resentment on the part of actual ranches. A novelty ranch often has a few animals around for atmosphere, but the owner may not get on a horse very often, if ever.
On a working ranch, a windshield cowboy might be someone who drives the ranch truck a lot, in which case the term may be used in goodhearted fun, rather than as a serious accusation. Riding skills are still considered a necessity for ranch hands at most working ranches, along with driving skills, so the term can carry some sting, however.
Riding is a very important part of Western culture, and most ranch employees pride themselves on being skilled riders; numerous ranches even send ranch hands to participate in rodeos, showcasing their skills. Because riding is such a crucial part of ranch life, the associations with the term “windshield cowboy” cut deeper than non-ranchers may understand, as the term is essentially a fundamental assault on one's character and skills.