A world might have been close to existing when Jon Gruden would have become the Indianapolis Colts' head coach, according to a recent article in The Athletic (subscription required) by Zak Keffer. Then owner Jim Irsay wanted that to happen, and when adding Gruden, Irsay also wanted Indy legend Peyton Manning to play a part in the makeover, too.
Manning would have become an executive, though in what exact fashion isn't known. His role might have been as general manager, at least in Irsay's dreams. Instead, the Colts owner couldn't entice Gruden to come to Indianapolis in early 2017, and Indy fans couldn't know how the future would have changed.
Keefer wrote, "(Gruden) was finishing his ninth season as the color analyst on ESPN’s Monday Night Football (in early 2017), and his time away only stoked the fascination of NFL owners. The longer Gruden was at ESPN, the more coveted a candidate he became, chased not only by Davis but also the Indianapolis Colts’ Jim Irsay, who earlier that year tried to pair Gruden with franchise icon Peyton Manning in an executive role."
Jim Irsay wanted to bring Jon Gruden and Peyton Manning together with the Indianapolis Colts
What happened was Chris Ballard was hired as general manager, and Ballard has cycled through head coaches while only making the playoffs twice in that span. The GM has never won the AFC South, and the last time the Colts were in the postseason was 2020. 2026 could be his final year with the team.
Still, hiring Jon Gruden might have led to very bad things, too. First of all, after joining the Raiders, who were still playing in Oakland at the time, Gruden wasn't overly successful for three-plus seasons. He resigned five games into his fourth season, never having achieved a winning record in a full season.
Even worse, Gruden was basically forced to quit after the New York Times discovered a number of emails the head coach had sent to Bruce Allen, Gruden's former general manager when he coached with the Tampa Bay Buccaneers, which are alleged to contain racist and misogynistic language.
Had the latter occurred while Jon Gruden was coaching with the Indianapolis Colts, the team would have not only been successful on the field, assuming Gruden had the same level of success he had with the Raiders, but the team would have been dealing with an embarrassing off-field issue, too.
As far as what role Peyton Manning would have filled, one will never know. The former quarterback didn't seem to want to be an executive with an NFL team, and one might wonder how he and Gruden would have gotten along, as the coach was often linked to Manning's alma mater, Tennessee, to be the new head coach, but never accepted the job.
At least Jim Irsay and Peyton Manning never had to find resolutions to the aftermath of the drama Jon Gruden left behind with the Raiders. Instead, the Indianapolis Colts' new regime simply needs to focus on winning football games, which hopefully they will do more of beginning in 2026.