Their Kushner
Older brother Jared is 37. He also went to Harvard, and was involved in various business and real estate-related pursuits. In 2006, he purchased the New York Observer, and ruined it. Despite having zero experience, he is now, for some reason, the senior adviser to the President of the United States, who happens to be his father-in-law. He is shady AF. He has a secret Instagram, and it sucks.
Winner: Karlie (and Josh)
[Photo via @ivankatrump]