2011 by Oxford University Press, Inc. All rights reserved. This article engages questions of canonicity, asking why Sally Watson's popular 1969 novel, Jade, never achieved critical recognition. It also suggests that Watson's tomboy characters, especially Jade, crossed a line in terms of their gender-bending performances, which, by the late 1960s, produced anxiety in adult critics, thus keeping Jade out of the canon. The article then proposes that reading Jade against its more canonical, more socially approved predecessors provides insight into the parameters of the tomboy tradition and what those parameters imply about twentieth-century understandings of femininity. It is suggested that Jade is a radical novel that appeared at a moment radical in some ways and conservative in others; to be palatable to those working within establishment venues such as public libraries and mainstream review outlets, it had to be presented-not altogether successfully-as a traditional romantic swashbuckler whose progressivism had more to do with race than with gender.