"What a train wreck," said Harrington.
The biggest reason, he said, is that there are just fewer jobs than there used to be.
But employers are also placing a higher value on education than ever before.
As a result, high school dropouts not only struggle to find jobs but make less money when they do.
"If you look at a male who was a high school dropout in 1980, he would have had an expected lifetime earnings of about a million dollars," said Harrington. "If you take that guy today … it would be about $480,000."
Making things even tougher, young dropouts are suddenly facing stiff competition from college graduates and older people for entry-level jobs.
"We're seeing people 65 and over in grocery stores [and] department stores," said Harrington. "Ten years ago, that was not something you'd see."
There is a positive spin on all the bleak numbers. Education makes a big difference on the labor market: Young adults citywide are 55 percent more likely to find work if they have a diploma.
But even as the economy sputters towards a rebound, Harrington said the outlook for young dropouts remains bleak.
"If you're a kid from Kensington, and you're a high school dropout, that recovery is mostly going to pass you by."