On February 14, 2012, during a podcast with Bill Simmons on Grantland.com, Ryan announced that he would retire after the 2012 Summer Olympics in London. Said Ryan, "I really and truly believe that my time has come and gone; that the dynamics of the business, of what it takes, what it means to be involved in the sports business with all the Tweeting and the blogging and all the stuff, and an audience with a different taste - it's not me anymore. I'm not comfortable." Ryan indicated that he would stay involved with sports in a part-time capacity after retirement, but is not interested in continuing at the pace he does now. Ryan's last day as a Red Sox reporter was July 16, 2012.