After graduating college in 1993, Rutenberg began working for the New York Daily News as a gossip stringer. He eventually worked his way up to becoming a general assignment reporter. In 1996, he was hired on staff and became a transit beat reporter. He left the Daily News in 1999 to worked as a TV reporter for the New York Observer. One year later, he began working for The New York Times where he was responsible for covering media and local politics. He has also served as City Hall Bureau Chief.