This paper explores the process of creating archives through an exploration of a range of archival sites in Chicago, Illinois. These sites contain objects believed to be of value that were once located in or referred to the area of the Maxwell Street Market, once the largest open air market in North America. The paper contributes to discussions of the geography of archives and archiving on the one hand, and the processes of evaluation that give objects value on the other. It does so by examining how different objects are given contrasting and competing values by different people in different places. These places include the formal archives, the place itself, a collection of objects stored for a possible museum in the future and a private residence in the city. Following an introduction to the area and a discussion of the nature of archives, three sets of gleaners are examined: journalists and photographers whose accounts and images can be found in the Chicago History Museum, the members of the Maxwell Street Historic Preservation Coalition and the Maxwell Street enthusiast and activist, Steve Balkin. The conclusion considers the different ways in which objects are valued in these different archives and demonstrates how archives are leaky places produced through a contested set of valuations concerning which objects count as worthy and significant.