In 2014, Gannon was enlisted as a play-by-play commentator for figure skating at the 2014 Winter Olympics in Sochi, Russia. NBC needed backup announcers for their daytime broadcasts of figure skating, and so at first, he was slotted to work with 1998 Olympic champion Tara Lipinski and three-time U.S. national champion Johnny Weir separately. The trio recognized their chemistry and requested that they call the competition together; the result was the 10 best weekday daytime ratings in NBC's history. They were promoted to the network's lead figure skating announcing team the following season. Lipinski and Weir reported that Gannon "upped his game" with his wardrobe after working with them. Lipinski called Gannon "dapper" and "stylish"; she and Weir reported that they had helped Gannon with accessories such as cuff links and Hermès pocket squares. In 2017, Gannon signed a five-year contract extension with NBC and the Golf Channel.