This insurance titan, who built Aon into a global powerhouse and now runs his own specialty insurance firm, is a loyalist whose generosity continues to shape two sources of fierce civic pride: the Bears (he’s a 20 percent owner) and his alma mater, Northwestern University. In December, the latter announced that Ryan will help fund the construction of a $220 million multi-use athletic complex.

Photograph: SCOTT STRAZZANTE/CHICAGO TRIBUNE