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 $n-d$. In particular,
we prove a new quadratic upper bound on the diameter of $3$-way axial transportation
polytopes defined by $1$-marginals. We also show that the Hirsch Conjecture holds for $p
\times 2$ classical transportation polytopes, but that there are infinitely-many
Hirsch-sharp classical transportation polytopes. Second, we present new results on
subpolytopes of transportation polytopes. We investigate, for example, a non-regular
triangulation of a subpolytope of the fourth Birkhoff polytope $B_4$. This implies the
existence of non-regular triangulations of all Birkhoff polytopes $B_n$ for $n \geq 4$. We
also study certain classes of network flow polytopes and prove new linear upper bounds for
their diameters.