We consider regression problems with binary weights. Such optimization problems are ubiquitous in quantized learning models and digital communication systems. A natural approach is to optimize the corresponding Lagrangian using variants of the gradient ascent-descent method. Such maximin techniques are still poorly understood even in the concave-convex case. The non-convex binary constraints may lead to spurious local minima. Interestingly, we prove that this approach is optimal in linear regression with low noise conditions as well as robust regression with a small number of outliers. Practically, the method also performs well in regression with cross entropy loss, as well as non-convex multi-layer neural networks. Taken together our approach highlights the potential of saddle-point optimization for learning constrained models.