Robert Kraft & Ricki Lander

Before buying one of the most dominant sports franchises of the early 21st century, Robert Kraft made quite a lucrative living by getting into the paper manufacturing business. From there, he bought the Patriots in the early ’90s, during which they were an ailing franchise.

mr.robertkraft via Instagram

While taking the Patriots into the stratosphere in terms of overall value (up to almost $4 billion as of 2019), he also took his dating game to new heights, too, with Ricki Lander. She’s taken to the modeling and even film scene, with one of her biggest roles coming in Ant-Man. She’s also almost 40 years younger than him.