November 30, 2008. That was the last time Jon Gruden was on the winning end of a football game as an NFL head coach. After that he lost 7-straight. Although the last three came a long time after the first four and for two different teams. That streak ended today.
It wasn’t easy. And at times it looked hopeless. And in fitting fashion, it simply couldn’t come in regulation. After starting his return to the Raiders with three straight losses. Jon Gruden finally notched his first win, beating the Browns 45-42 in overtime.
Tasting victory as ahead coach is something Gruden hasn’t felt in a very long time.