Though the play also boasted the award-winning talents of Ruby Dee and Paul Winfield, the production was troubled from the start. New York Times reviewer Frank Rich wrote, "While it's easy to name a recent Broadway play or two as awful as Checkmates, it may be necessary to get out the scrapbooks to recall one quite so amateurish and boring."
Following its August opening, the production frequently played to houses below half capacity; in December, the show's co-producer Michael Harris was convicted of attempted murder in connection with an international cocaine ring. Shortly thereafter, the show announced it would close Jan. 1, 1989. But Washington's rising star emerged untarnished, and the following year he would win his first Academy Award for his performance in "Glory."