Robert Harmon Director Tom Selleck Jesse Stone Actor, Executive Producer Kathy Baker Rose Gammon Actor Kohl Sudduth Luther "Suitcase" Simpson Actor Leslie Hope Sidney Greenstreet Actor Stephen McHattie Captain Healy Actor William Sadler Gino Fish Actor Jessica Hecht Stephanie Morton Actor Joanna Miles Mrs. Steinberg Actor Fulvio Cecere Teddy Leaf Actor William Devane Dr. Dix Actor Camryn Manheim Elizabeth Blue Actor Jeremy Akerman Councilman Carter Hansen Actor John Beale Dr. Perkins Actor Kerri Smith Sister Mary John Actor Gary Levert William Butler Actor Todd Hofley Alan Actor Tom Gallant Councilman Comden Actor Glenn Lefchak Homeless Guy Actor Brian Heighton Boston Doctor Actor Dawn McKelvie Cyr Nurse 1 Actor Sherry Smith Nurse 2 Actor Jonathan Brass Michael Actor Philip Dinn Dispatch Officer Actor Scott Owen Teddy's Sidekick Actor Ruby Carr Runaway Girl Actor Steve Morgan Bartender Actor Gil Anderson Jenn Actor Ronni Kern Screenwriter Steven Brandman Producer Michael Brandman Executive Producer Rene Ohashi Cinematographer Steven Cohen Film Editing Jeff Beal Original Music William Fleming Production Design Angela Murphy Art Director Brian Enman Set Decoration Betsy Cox Costume Design Steve Brooksbank Casting Mary Jo Slater Casting