1. James Pennington
Always ahead of the educational curve, Yale played host to its first black student when slavery was still thriving. But if you're under the impression that the gesture was a beacon of racial progress, think again.
Born a slave and later escaping as a fugitive, James Pembroke (later Pennington) settled in New Haven, CT some time around 1834. He became the first black man to attend classes at Yale that year, but never became the first to graduate because the university didn't permit him to earn a degree. The most he could do was observe classes at the divinity school for no academic credit, which bears an uncomfortable resemblance to one of his earlier ventures. All work, no pay.