Grant DePorter


The CEO of Harry Caray’s Restaurant Group could be called Chicago’s Man About Town

Grant DePorter grew up living at the Hyatt Regency Chicago. His father, Donald DePorter, ran the hotel and Grant lived out every teenage boy’s dream: having parties at the Hyatt every weekend. Grant’s dad also founded Chicago Gateway Green, so we have him to thank for the beautification initiative.

Harry Caray’s first restaurant opened in River North back in 1987, and Grant has worked there since 1989. He became president in the mid ‘90s and was eventually named CEO. He’s been a huge Cubs fan since he can remember, and his name may ring a bell because he was that fan who paid nearly $114,000 for a baseball from the game when the Cubs were defeated in the 2003 National League Series.  The infamous ball was blown up in front of Harry Caray’s original restaurant, making for a priceless PR moment. “The auction started at $5,000,” he recalls, adding that he only planned on bidding as high as $30,000. “The next thing you know, it’s 1:00am and I bid $114,000!” All in the name of needing what he calls a “cathartic release” from the pain of the Cubs’ losing, yet again.

Despite critics who worried what would happen to Harry Caray’s restaurants after the former Cubs announcer passed away in 1998, Grant is proudly running seven restaurants now, including Harry Caray’s 7th Inning Stretch (combined with the new Chicago Sports Museum) on the seventh floor of Water Tower Place. The menu features American favorites ‘reimagined’ by Chef Joseph Rosetti. Think craft burgers, Neapolitan-style pizza, large entrée salads; everything is made in-house, with the exception of Homer’s ice cream and Angelo’s gelato.

The museum showcases memorabilia and it’s also interactive. Some of Grant’s favorites include a game where visitors virtually experience what it’s like to be tackled by Bears Hall of Famer Richard Dent. The Superstition Room is dedicated to properly depicting what Grant refers to as “the most superstitious city in the world.” After all, most locals do blame a goat and headphone-wearing fan (aka Steve Bartman) for the Cubs losing streak ‘curse.’

Grant’s favorite thing about Chicago is the “great Midwestern attitude and hospitality.” When will the Cubs win the World Series? “2015,” he says with confidence, “because that’s the year they won in the movie Back To The Future Part II.” And his favorite baseball player to ever live is undeniably Mr. Cub, Ernie Banks.

Another fun factoid: Grant was once mistaken as pop singer Kesha’s agent when he took his twin 18-year-old daughters to the concert and showed up in his suit. “People were sending me over drinks all night,” he remembers, laughing. Perhaps Grant is an agent of some sort, representing all of Chicago’s oh-so-loyal Cubs fans. Cheers to that!

Kasia Jarosz Photographs

Sarah Levy

About Sarah Levy Imberman

Sarah Levy delighted millions as the owner and proprietor of Sarah's Pastries & Candies, one of Chicago's most popular confectionaries since its opening in 2004. A graduate of Northwestern University and the French Pastry School, Ms. Levy is the author of Sweetness: Delicious Baked Treats for Every Occasion and the winner of the Food Network Challenge. She’s been featured in USA TodayBetter Homes and Gardens and the Chicago Tribune, among many others. Ms. Levy's now doing business as S. Levy Foods, and is a leader in the airport food concession business.