Drew joined OnMilwaukee.com on May 1, 2006, after spending the previous 19 ½ years at the Milwaukee Journal Sentinel and its predecessor, The Milwaukee Journal. Though he did some freelance work for both the Features department and Wisconsin Magazine, Drew spent most his time at the newspaper in the sports department. He covered the Brewers and Major League Baseball for 11 seasons, was named president of the Baseball Writers' Association of America in 2004 and served as one of three official scorers for two All-Star Games (2002 in Milwaukee and 2004 in Houston).

During his time covering sports, Drew did freelance work for The Sporting News, Baseball America, Sports Illustrated and numerous other publications. In addition to his writing duties, Drew is host of "The D-List,'' which airs daily from 11 a.m. to 2 p.m. on 540 ESPN. During the baseball season, Drew discusses the Brewers and baseball on "The Bob and Brian Morning Show,'' which airs on WHQG (102.9 FM) in Milwaukee and is syndicated statewide. Drew also does some work as a sideline reporter on Brewers and Bucks broadcasts for Fox Sports Wisconsin. 

Drew grew up in Menomonee Falls and graduated from the University of Wisconsin-Milwaukee, where he spent a semester on the men's basketball team "before they got good.'' He lives in the western suburbs with his wife and daughter.