While he wasn’t an onstage performing member of the group, road manager Thomas O’Keefe was a part of Whiskeytown for longer than just about anybody except for Ryan and Caitlin. So he was there for some of the most notable onstage dust-ups of the “Losering” story, including Kansas City, East Lansing and San Francisco — and if Caitlin was the one doing the apologizing afterward, O’Keefe was the one who had to pick up the pieces. Fortunately for him, he is a stout individual that few people want to mess with.
Post-Whiskeytown, O’Keefe has managed the Ohio rock band Watershed (subject of this book, which you should read immediately if you haven’t already); and also worked as road manager for Train, a fairly ginormous pop band from San Francisco. For more on just how busy Train keeps him, see this. One reason Train has been so much more successful than Whiskeytown is that they’re willing to play the game.
“I always figured Ryan would be Tom Waits, someone you and I know but the average joker doesn’t,” O’Keefe told me in 2010. “Going to work for Train has shown me the work they do to be successful. They still get up at 6 a.m. and visit the radio station. The amount of that kind of thing it takes to be massive is incredible. We just did two weeks of top-40 shows with Katy Perry, and that was just us kissing butt at the radio stations that played us all year. But it’s a necessary evil, and Ryan would never ever do that. So he’ll never have the commercial success that Train has, but that’s never been his motivation, either.”