QSolved Question : All the satellite offices have to route everything to Cleveland via fiber then the traffic passes across the DS3 to New York. The other part of the question is, will HSRP work if the Cleveland location is physically destroyed and the DS3 is completely non-functional, and the fiber is completely non-functional at Cleveland. Will Columbus' router with HSRP route traffic to New York via fiber? If not, is it possible to make it so it does?
QSolved Answer : Short answer is no. HSRP functions with routers on the same lan segment (or vlan) not over distance like you suggest. From the diagram, Columbus is nothing more than another sattelite.
Assuming a failure at CLE and the DS-3, As long as NY has a route (logical and physical) to the sattelites, traffic should flow.
So, your issue is more one of a routing policy. Prefer the DS-3 over the fiber link at the NY router.