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In recent years, the Knight News Challenge has emerged as one of the most important forums for stimulating innovation in digital journalism, and as a salient marker of the Knight Foundation's influence in the field. Yet, the scholarly literature has yet to unpack this contest: its design and execution; the applicants it attracts and the winners it funds; and the normative aims about the future of journalism that may be revealed in this process. This paper addresses that by examining content analysis data for nearly 5,000 applications to the Knight News Challenge, exploring the distinguishing features of applicants, finalists, and winners-and how particular features are associated with one's proposal advancing in the contest. A logistic regression suggests that, among other factors, those applications that advanced to the finalist and winner stages tended to include forms of participation (e.g., "user manipulation" and "crowdsourcing") as well as other features (e.g., software development) not typically associated with journalism. These findings are placed in the context of the Knight Foundation's broader efforts to shape journalism innovation.