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Remembering Legend Len Caldeira

Chicago Other

Chicago real estate lost an icon this week. JLL managing director Len Caldeira died on Sept. 7 after a battle with cancer. He was 71.


Len’s 45-plus year career included time at LaSalle Partners and Cushman & Wakefield. He launched Staubach's industrial team in Chicago in 2001, before JLL acquired Staubach in 2008. He completed deals in 17 states totaling more than 6,000 acres and many millions of square feet for clients ranging from Andrew Corp, Tribune Co and RR Donnelley, to Rubbermaid and Crate & Barrel. He told Bisnow in 2010 he considered himself a “closet developer” responsible for finding the best use for a piece of land and bringing the right people to the deal.


Len served as a mentor to younger brokers entering the industry. JLL managing director Fred Schuler says Len was constantly upbeat, never said no to a challenge, and always saw the inherent dignity in people and the work they did. Fred says Len taught him that details mattered and told a story when they stopped for a late lunch one Friday afternoon. Fred asked Len where he developed that sense of dignity. Len, who grew up in a mill town, said it came from his father, who worked in a mill but went to and returned from work every day in a suit. JLL managing director and head of industrial brokerage Trevor Ragsdale got his start in the industry under Len at Staubach in 2001. He says Len was a great counterbalance to his aggressiveness as a young broker entering the business, and taught him patience and to keep things in perspective. Trevor recalls a holiday party where his now-wife Lindsey spilled wine on a Christmas tie Len wore every year. Len, who told Trevor earlier he couldn’t wait for the holidays to wear the tie, comforted a mortified Lindsey, saying, “That’s OK. I never liked the tie, anyway.”


Len was a past president of the Chicago chapters of SIOR and NAIOP, emceed the annual NAIOP awards dinner for years and received that group’s Award for Excellence in 2010. Before his real estate career, Len was an Army Intelligence Officer in Vietnam. Fred and Trevor said Len and wife Chantel loved to host employees aboard their beloved sailboat, "Vamanos." He was also a passionate runner. In addition to Chantel, Len is survived by adult sons Len Jr. and Jason, daughter-in-law Erin, and grandchildren Emmit and Julian. Visitation for Len will be tomorrow, Sept. 11, at Hallowell & James Funeral Home, 1025 W 55th in Countryside, from 3pm to 9pm. A memorial service and mass will be held at St. Alphonsus Catholic Church, 1429 W Wellington, Sept. 19, at 11am, with a celebration of his life to follow. Donations in Len’s name can be made to the Bear Necessities Pediatric Cancer Foundation.