In September 2006, Wolf joined WMAQ-TV (NBC 5) as a traffic and sports reporter. "Traffic and sports? I'm not the first Channel 5 multitasker," Wolf joked to the Chicago Sun-Times in August 2006. "(Legendary Chicago TV anchor) Floyd Kalber once took it upon himself to do the news and weather. He was (nicknamed) 'The Big Tuna.' I'm just a little sardine." In January 2007, Wolf became the host of WMAQ-TV's "Barely Today," a freewheeling news and talk show that aired at 4:30 a.m. and that involved him engaging in banter with news anchor Ellee Pai Hong and weatherman Andy Avalos. "I think 4:30 in the morning is a little too prime time-ish for me," Wolf joked to the Chicago Sun-Times upon being named the host of "Barely Today." "What I was really looking for was a once-a-year show to be aired on the night that Daylight saving time ends in that one extra hour that you get at 2 in the morning."