In December 2005, 11 months after Gundy was tabbed as OSU's head football coach, billionaire OSU alumnus T. Boone Pickens donated $165 million to the athletic program. It set a record for the largest single gift given to an NCAA program and came after he donated $70 million two years prior.

In the final years of his tenure at Oklahoma State, Mike Gundy spoke candidly about how NIL impacted things in Stillwater. He made it clear he didn’t want to negotiate mid-season, though he helped lead the charge to put QR codes on players’ helmets to help with that support.