Dale Wiley has tried over a hundred civil and criminal cases before judges and juries, including murder and sexual assault cases, major personal injury cases and family law matters. He served as the President of the Missouri 39th Bar Association in 2000, and in 2004 was nominated for the Lon O. Hocker Award as the outstanding young trial lawyer in Missouri. He served from 2006-2009 on the American Association for Justice's prestigious Press Committee, and was a member of the AAJ's New Lawyer Division Board of Directors from 2004-2006. Wiley was named Chairman of the NLD Board of Governor's Committee in 2006.
From 1990-94, Wiley was the editor of Cadenza, the weekly Washington University arts paper, where he interviewed Emmylou Harris, Randy Travis, Ray Manzarek, John Doe, Clark Terry, Joe Henry, Blind Melon, Alison Krauss, Juliana Hatfield, 2-Live Crew, Hugh Masekela, David Murray, and Jeff Tweedy, among others. In that role, he was an early supporter of the burgeoning "alt-country" scene, as it was known then, being one of the few St. Louis writers paying attention to Uncle Tupelo, Blue Mountain, the Bottlerockets and the like. He has also written for the St. Louis Post-Dispatch, St. Louis Business Journal and Maybelle. In concert booking, Wiley has brought diverse acts such as Riders in the Sky, The Mavericks, Junior Brown, George Clinton, Maria Muldaur, Olivia Tremor Control, Skeleton Key, Apples in Stereo, Zeena Parkins, Ronnie Dawson, Kelly Joe Phelps, The Squirrel Nut Zippers, Lavay Smith, and The Hot Club of Cowtown to Missouri venues.
Wiley has given Continuing Legal Education programs for AAJ, and has been asked on multiple occasions by other attorneys to help in personal injury and insurance interpretation questions.
Wiley has also worked for The Muny in St. Louis, The Edison Theatre at Washington University, Metrotix and the National Endowment for the Arts in Washington, D.C., in the Presenting and Commissioning Department, and is past President of the Board of Directors of Twin Bridges Development Corporation, a non-profit group bringing music and other arts events to Crane and to Southwest Missouri.