Year(s) of endorsement: 2008-2013
Estimated money made: $10 million
Everyone loves to make fun of Tony Romo (and with good reason), but there's no doubting his endorsement power. The Cowboys' quarterback signed with the famous jacket-maker Starter in 2008, inking what was thought to be the richest endorsement deal ever given to an NFL player. Anyone who watches football knows about Romo's ubiquitous backwards Starter hat, so obviously the company did a good job getting their name out there. Maybe it's a telling sign, though, that they did not renew his contract this year; they could see the Cowboys' fall coming before the rest of us.