News Anchor, NewsChannel 5, 41
/ Why he’s interesting / He’s the new face on NewsChannel 5’s evening newscasts, filling the anchor seat opposite Danita Harris that’s been largely vacant since Ted Henry’s 2009 retirement. Flanagan arrived with big-market chops, including previous posts in Dallas, Iowa and San Francisco.
/ Breaking and entering / Flanagan needed an audition tape to get his first job, but the Connecticut station he interned for wouldn’t give him on-air experience. “So I basically sweet-talked my way past a security guard at 5:30 on a Saturday morning when I knew very few people would be there.” His wife Kristin taped his fake newscast on a camcorder, and it got him a job. And that Connecticut station? “They never found out. But now they will.”
/ Most memorable interview / A then-Iowa-based Flanagan did two interviews with Barack Obama during the 2008 election season, including one at an auto body shop with a car on a lift. “We were as close as you can get to sitting under a car. I look back and think, He’s now president of the United States, and I sat under a car with him.”
/ Keeping score / He was a sports reporter early in his career, and he often had to get creative in the newsroom. “If we were looking for sports scores, you couldn’t get them from ESPN or anything, so we called a bookie.” In a small station with minimal staff, Flanagan sometimes recruited Kristin to help. She would call the bookie for scores 10 minutes before his air time. “The first time, [the bookie] said, ‘Sweetheart, does your daddy know that you’re calling?’ ”
/ Team loyalties / He’s a lifelong fan of the Dallas Cowboys, “but now I’m on board with the Browns. And the Indians. And any team that plays against LeBron James.”
/ Converted Clevelander / “Nationally, Cleveland gets that reputation, like ‘Oh, why would you want to go there?’ But when we came here, everyone was so fantastic. We just knew this is where we want to be.”
/ On being one of the Most Interesting People / “My wife said, ‘Are you sure they have the right guy?’ Being around these folks who were chosen, it’s pretty humbling.”