The maximum rectilinear crossing number of a graph is the maximum number of crossings in a good straight-line drawing of in the plane. In a good drawing, any two edges intersect in at most one point (counting endpoints), no three edges have an interior point in common, and edges do not contain vertices in their interior. A spider is a subdivision of . We provide both upper and lower bounds for the maximum rectilinear crossing number of spiders. While there are not many results on the maximum rectilinear crossing numbers of infinite families of graphs, our methods can be used to find the exact maximum rectilinear crossing number of where each edge is subdivided exactly once. This is a first step towards calculating the maximum rectilinear crossing number of arbitrary trees.