Truckers used to make $110K per year on average. Now many are homeless. So what happened? We dug into it as part of our new Class Room series, which looks at how jobs that used to provide a solid, middle class life now barely provide a living. With trucking, that story starts with deregulation. Big Box stores like Walmart were allowed to crush worker power and wages across an entire industry. Now there’s a perpetual trucker shortage as drivers get sick of low wages, long hours, and constant surveillance.