Jim Nagle: From Courtroom to Comeback, A Force Behind One of Illinois’ Most Inspiring Revivals
As owner of The Drake Oak Brook, Autograph Collection and a Village of Oak Brook trustee, Jim Nagle has become a driving force behind one of Illinois’ most compelling comeback stories. A former Chicago attorney and third-generation lawyer, Nagle shifted his career trajectory from law to real estate preservation and civic leadership—breathing new life into a suburban landmark and the community around it. Formerly a golden-age hideout for stars like Frank Sinatra and Rock Hudson, he has transformed the Midwest landmark hotel over the last decade from a dilapidated, ponzi-scheme–tainted property into a Condé Nast–recognized destination and helped lead a $59M financial turnaround for the entire city of Oak Brook, located twenty minutes outside of Chicago.
Nagle’s passion for revitalizing the communities he grew up in has fueled both his private and public-sector efforts. As a Village Trustee over the last four years, he has helped strengthen public safety through new crime-fighting tech, introduced zero-based budgeting, erased multi-million-dollar deficits and implemented more transparent bidding practices. As a hotelier, he personally took on The Drake Oak Brook’s restoration—painting walls, training a loyal crew, and repurposing staff to keep everyone employed during the pandemic.
Under Nagle’s leadership, the 154-room property has become a symbol of resilience and innovation, with guest experiences ranging from evening astronomy picnics new-build restaurants brining new cuisines to Oak Brook to an upcoming redesign of the region’s largest gardens. Inspired by conversations with Richard Branson, Nagle remains focused on carrying the property’s legacy into the future and onto the global stage—expanding its success through upcoming residences, overseas partnerships, and more. The hotel was recently named No. 7 in the Midwest by Condé Nast Traveler’s Readers’ Choice Awards and No. 55 on US News & World Report’s Best Hotels in Chicago.
For Nagle, the secret isn’t just in the name—it’s in the people. “You can have a beautiful hotel, but it’s a great team that makes it special,” he says.
Photo credit to The Drake Oak Brook, Autograph Collection.
