This dissertation investigates the geometric combinatorics of convex polytopes and connections to the behavior of the simplex method for linear programming. We focus our attention on transportation polytopes, which are sets of all tables of non-negative real numbers satisfying certain summation conditions. Transportation problems are, in many ways, the simplest kind of linear programs and thus have a rich combinatorial structure. First, we give new results on the diameters of certain classes of transportation polytopes and their relation to the Hirsch Conjecture, which asserts that the diameter of every $d$-dimensional convex polytope with $n$ facets is bounded above by $n-d$. I...