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The Finisher's Need for Speed

Hiffman's 'garage' in Joliet is brightly lit and pristine, with big-screen TVs and bedrooms upstairs.

By Mark Vruno

Dennis “Denny” Hiffman ’60 may not consider himself much of an athlete, per se, but he has always enjoyed competing. “Fenwick channeled my competitiveness,” he believes. Denny was a self-taught golfer at Columbus Park in the Austin neighborhood on Chicago’s far West Side and also golfed on the Friars’ team.

Before the school’s Auditorium was completed, he and his classmates smacked golf balls into a net strung where the “freshmen” balcony would be later. Denny also learned the 16-inch “Chicago” softball game and “played until I was 60,” he says. And he has had a passion for cars since before he could drive. “I bought my first junker, a ’52 Chevy, the day of my 16th birthday and drove it to Fenwick,” Hiffman remembers. Over 40 years ago he was lured into auto crossing, where drivers get timed maneuvering around orange cones in a parking lot. That led to 20 years of Saturday short-track, stock car racing in Wisconsin; Hiffman found himself atop the Winner's Circle podium more than 100 times.

Then in 2004 Denny took up road racing. And now, at age 75, he races cars against competition 50 to 55 years his junior. He won the Porsche Club of America (PCA) national championship in 2015 and 2013, took the 944 Cup in 2016 and also won several regional championships. Eighty-five cars in the PCA series ran timed races of 45 and 90 minutes in length. In 2015 Hiffman won 16 of 33 races.

While Hiffman and his Greasy Side Down (GSD) racing team may not always cross the finish line first, they always cross it, which means they race smart and don’t crash their 230-horse power, 4-cylinder Porsche. Top speeds can exceed 150 miles per hour.

“A lot of 18-year-olds and twenty-somethings behind the wheel are over-zealous,” he observes from experience. “Their mentality is to ‘either win or crash.’” Hiffman and GSD partner Tom Collins, who “builds shopping centers” when they’re not racing, according to Denny, subscribe to a different motto: To finish first, first you must finish.

 “I always finish,” the proud driver proclaims, matter-of factly. But why would a man in his mid-70s want to suit up and sit in the hot seat, quite literally? A race car’s interior temperatures can exceed 125 degrees Fahrenheit in the summer. These days, Hiffman wears a $1,200 cooling suit that circulates ice water through a system of built-in “veins” or tiny hoses. “Racing is a true sickness,” jokes Denny. “Once you have it, you’re hooked.”


The Autobahn Country Club in Joliet is Hiffman's home away from home. Its 3.5-mile course features 22 turns.

Watch Video on Hiffman's Racing Passion

The racing aficionado has been driving for so long that one of his former pit crew member’s kids is now working for stock-car racer Kyle Busch and his team; another was 2016 Rookie of the Year at Slinger Speedway in Wisconsin. But being the oldest guy on the circuit doesn’t deter Denny Hiffman; in fact, being a “racing elder” fuels him.

Being the smallest kid in his class didn’t faze him either, says the now 5’6” Denny, donning a racing cap. Academically, “I was near the bottom of my class, too,” he offers, adding that he was a “greaser” from the South Side who always had difficulty fitting in socially at Fenwick. Yet Hiffman has said that the school saved his life. “As painful as the constant discipline was, Fenwick truly gave me a course to follow,” he explains. “Most of my friends back on the South Side got into trouble, some serious. Hiffman thinks so much of his Fenwick experience that he sent his three sons – the late John ’90, Matt ’94 and Dan ’95 -- to school there, is a FHS Life Trustee and Board Member of the Fenwick Foundation.

Taking detours

Twenty years after Fenwick, faculty member Father Bernacki became the Hiffman family’s priest. After a reunion event, “we got reacquainted at the Loon Café [in River Grove],” Denny remembers, which at the time was owned by a Fenwick classmate, the late John Stamm.

Hiffman always has been a nose-to-the-grindstone worker. In addition to caddying at Riverside Golf Club, he had several different jobs while enrolled at Fenwick. “I worked in a dry-cleaning shop, as a milkman and was a [door-to-door] Fuller Brush man. He credits the work ethic to his mother and father. “It was ingrained in me,” says Denny, adding that it was his strong-willed Irish mom who “made” him go to the Catholic high school in Oak Park after the Hiffman family moved from the South Side.

After graduating from Fenwick, Denny spent one semester at Loyola University Chicago while driving a taxi cab to earn cash, “but college wasn’t for me,” he admits – at least not yet. So, he enlisted in the U.S. Marine Corps. “The discipline [from Fenwick] transferred over,” he notes, adding that Boot Camp was not that difficult for him despite his diminutive size. After serving his country, Hiffman returned to Loyola and was a much “more serious student.”

Fast forward to six years ago, when Hiffman stepped down as chief executive officer of NAI Hiffman, the real-estate brokerage firm he founded in 2000 (see below). He remains as Chairman of the Board, more focused on client relationships and strategy -- 18 months ago the firm sold Oak Brook Promenade to Retail Properties of America for $66 million. Denny passed the day-to-day management and operations to CEO David Petersen and COO Michael Flynn ’77, another Friar who began working for him in 1984.

“I work 24/7,” he says. “Real estate happens all the time,” which is why he prefers taking detours during his racing-related travels to Florida, Georgia, Louisiana, Minnesota, New York, Pennsylvania, Texas and other states. He is a former River Forest resident who now lives in Oak Brook. But Hiffman spends about half the week in his 6,000-square-foot, two-story “garage” at the Autobahn Country Club (ABCC,, which was built 11 years ago and features a 3.5-mile, 22-turn race course on some 1,500 acres of former farmland in Joliet, IL. Always the businessman, Denny is helping to develop 2,000 adjacent acres into warehouses.

There are 65 lots and 45 pristine, brightly lit garages at the ABCC, whose management adds two to three new garages – complete with big-screen televisions and stereo speakers -- per year. Like many others, the GSD facility also has living quarters and two bedrooms upstairs as well as a track-facing deck that can accommodate up to 60 racing fans. (The Bobby Rahal race team’s gray garage is nearby.) Centrally located 45 minutes from Chicago and Barrington, “and not too far from Springfield,” Denny points out, ABCC is one of about a dozen similar racing facilities in the U.S.

Hiffman sits on the board as one of two at-large members along with ABCC’s three founders, who are permanent members. “There are 375 [club] members,” he reports. “Our goal is 500.” Full membership in the Autobahn CC consists of a $40,000 initiation fee and annual dues of $5,000. Social memberships charge no initiation fee and $4,000 annual dues for one month of track use per year. “Corporate memberships for four people cost $125,000,” Hiffman adds.

Four racing garages service cars for a fee. Condos and “Garage Mahals” on site to store cars are available for about $1 million, according to a July 2017 article in the Chicago Tribune. Less expensive rental garages also are available.

Fenwick connections

NAI Hiffman employs some 180 people, approximately 5% of whom went to Fenwick. In addition to Mike Flynn, another 10 or so employees also are Friars. “There is Jim Adler [’90], who was a good baseball player, and Dan O’Neill [’89], my son Dan, Packy Doyle [’07], Marek Burchett [’12] … and a Cooney [Kevin ’10], I think,” Denny says. “All of them got the jobs on their own,” he stresses, but listing Fenwick on the résumé never hurts.

Hiffman has been racing since the age of about 30; competitively since the late 1970s/early ’80s. His other passion in life, real estate, for more than 40 years as well.

“I knew I wanted to sell,” he says, “but I couldn’t make the grade at blue-chip companies like IBM and Xerox.” Young Denny sought the advice of fellow Friar Jack Gearen ’32, a mentor and “grand old man at [Ascension] church” for whom Fenwick’s library is named. Mr. Gearen told him he had two choices at the time, in the late 1960s: go into either mortgage banking or real-estate brokering. Hiffman chose the latter and has never looked back -- expect in his rearview mirror while racing, of course. “I made my own way, working six to seven days a week in 1968,” he reflects.

In 1972 he started a job with Hawthorn Realty Group and focused on industrial properties for the next five years. In late 1981 he founded HSA to serve the needs of corporate real estate; the company had a 19-year run and grew into the largest independently owned commercial real-estate firm in Chicago. Kensington Center, a 300-acre office/research/industrial park in Mount Prospect, is one of the feathers in HSA and Hiffman’s cap: Denny exclusively represented his client, OPUS, on the deal.

When he’s not behind the wheel racing, Hiffman has been working hard, honing his craft for nearly 50 years. In ’77 he was hired away to start MRX/Midwest Realty Exchange, which later was sold to Grubb & Ellis (and became the basis for its Chicago office). In ’99, Denny became Chairman and CEO of NAI Hiffman, which was formerly the Brokerage Division of HSA. In 2001, NAI Hiffman purchased Scribcor Real Estate Services, a 110 year old management and brokerage services company, which brought in accounts such as the Wrigley Co., St. Paul Travelers, UBS Brinson and the MacArthur Foundation.

Today, NAI Hiffman is the largest privately owned commercial real-estate brokerage in Illinois. Based in Oakbrook Terrace, the firm provides leasing, management and investment sales representation for owners and occupiers of commercial real estate in the Chicago metro market. It leases and manages a 77 million-square-foot portfolio of more than 600 commercial properties throughout metropolitan Chicago, Northwest Indiana and Southeast Wisconsin. NAI Global offices are leaders in their local markets and work in unison to provide clients with exceptional solutions to their commercial real estate needs. NAI Global has more than 400 offices strategically located throughout the world, with 7,000 local market professionals, handling over $20 billion in transaction value and managing 425 million-square-feet of property. Hiffman was formerly the Chairman of NAI Global’s Advisory Board.

Denny himself has served as a general partner in the development and/or acquisition of 1.25 million square feet of office buildings, including: the Old Orchard Plaza in Skokie; the Midwest Office Center and One Oakbrook Terrace in Oakbrook Terrace; and some 2.5 million square feet of retail shopping centers such as Orland Park Place and Main Street Village in Orland Park, Broadview Village Square and Broadway Center in Chicago as well as 12 million square feet of industrial space throughout the United States.

He also owned Coogan’s Riverside Saloon on Upper Wacker Drive (180 N. Wacker) between Randolph and Lake streets in the Loop. The location was one of his firm’s former properties: the six-story Great Lakes Building, built in 1912, which Hiffman and his partners sold nine years ago.

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