Jay and Jon Gruden Have a Forgotten Older Brother

Jon and Jay Gruden are prominent names in NFL coaching. While sometimes controversial — in part due to systemic issues with the franchises they are associated with — the two are reliable picks for top jobs in the league. In terms of holding down successful careers at the highest level of the game, the Grudens are something of a dynasty.

The story of the Gruden family in football starts a generation back. Their father Jim Gruden was a prominent figure at all levels of the sport. He topped out as the running backs coach for the Tampa Bay Buccaneers from 1982-1983.

And, as success comes in many forms, there is actually a third Gruden brother that deserves a spotlight for entirely different reasons. We’ll get to that in a minute. First, let’s take a look at how Jim’s two football-focused boys proved themselves worthy of the biggest jobs in football.

Jon Gruden’s climb to becoming the Raiders’ head coach

The Gruden brothers grew up moving around the country, following their father’s climb up the coaching ranks. The experience clearly wasn’t traumatic overall, because two out of the three boys decided to become coaches just like their father.

Jon Gruden’s approach to football was entirely about the grind. He lacked some of the athletic prowess of his brother Jay. He set out to make up for that by getting up earlier and working harder than anyone around him.

After a three year run as The University of Dayton’s quarterback, he pivoted to coaching. Starting as a graduate assistant at the University of Tennessee from 1986-1987, his path to the NFL began.

He finally ascended to head coach with the Oakland Raiders in 1998. By 2000, Jon led the team to their most successful season in a decade. But the Tampa Bay Buccaneers — in the Gruden business since Jim’s time there — made a big offer to get Jay on board. Disappointed Oakland fans watched their rising head coach walk.

Worse still for the Raiders faithful, Gruden’s revitalized Bucs defeated the Raiders in Super Bowl XXXVII. Jon stayed in Tampa Bay until 2008, when he was fired after ending the season with four brutal losses in a row.

For a decade, Jon was on the sidelines watching his brother Jay’s career develop. Then the Raiders came calling again. He’s been at the helm of the team as they transition from Oakland to their upcoming home in Las Vegas.

Jay Gruden’s offensive-focused history

Jay was the more athletic of the two Gruden boys who showed interest in football. His natural gifts propelled him, but he was keenly aware of Jon’s incredible work ethic. He was inspired to fight hard to cut his own successful path through the game.

While he didn’t make the NFL cut as a player, Jay spent the first half of the ’90s playing professionally with the AFL. He won the AFL MVP as a quarterback in 1992, and played an instrumental role in several deep playoff runs. Then he found the calling that most of the Gruden clan seems to fall for: coaching.

Even while coaching in the AFL he continued playing. He never led a team to the playoffs as a player in the back half of his career. But he did lead two different AFL teams to 10-4 records in the early 2000s. Because of how the AFL and NFL seasons lined up, he served as an assistant offensive coach for the Buccaneers during this time.

When Jon was fired from Tampa Bay, Jay followed him out the door. He worked as an offensive coordinator for the Cincinnati Bengals from 2011-2013. Then he landed his first head coaching job with the Washington Redskins.

His first season ended in a disappointing last-place finish. A big turnaround in 2015 gave Washington fans hope: 9-7 season and a playoff appearance. But subsequent seasons trended back downwards, leading to Jay’s firing in 2019.

The Jacksonville Jaguars quickly scooped up Jay for another shot at the offensive coordinator spot. It may well be a reprieve from the notorious chaos of the Redskins organization.

The third Gruden brother’s life well outside of football

One Gruden brother sidestepped any possibility of the chaos of working for an NFL team altogether. Breaking with the family tradition, James Gruden found his calling in medicine.

James F. Gruden, M.D., is a highly-regarded radiologist primarily based out of New York City. He also maintains two satellite locations associated with the famed Mayo Clinic. Similar to the intriguing career paths of the Bayless brothers, it seems that each Gruden brother reached the heights of their respective crafts. Even the one that skipped sports entirely.