Jeffrey has been reviewing films professionally since he was a senior in high school and wrote reviews for his home-town paper, the Erie Times News. He earned his degree in journalism at Marquette University, where he wrote reviews for the school newspaper, the Marquette Tribune. Most recently he was the film critic for the Northwest Herald in Crystal Lake, Illinois, and continues to submit reviews to the Northwest Herald and its sister paper, the Kane County Chronicle
Jeffrey placed second in the 2002 and 2003 Illinois Press Association competitions for reviews (Division E). In 2005 and 2006 he was a finalist in the Chicago Headline Club's prestigious Peter Lisagor Award. For both years he was the only Chicago-area film critic nominated in the entertainment writing category.
He has served as a board member for the Chicago Film Critics Association.