Chicago
"In our early 20s, we looked out at the city with a sense of awe, yet also confidence: We’re gonna do things here."
For many years, I’d walk down to Wolf Point along the Chicago River and recline in one of its ever-present Adirondack lawn chairs. This was my favorite place to relax and savor the charm of my native city. Yet for so long, I didn’t know it was the exact point where Chicago was born.
Wolf Point is where the north, south and main branches of the river converge. Early explorers would stop at the intersection to trade and socialize. Named after the Indian who lived on the river’s west bank in the 1830s, Mo-ah-way (translation: “the wolf”), it’s also where the Sauganash hotel was built — where Chicago’s first elections were held.
Each spring/summer, when I return to my home city, and even just stroll downtown for a few hours, the unique history of the place sucks me right back in. And it feels like everywhere I turn, Chicago’s landmarks are intertwined with my own personal nostalgia.
Just above Wolf Point sits the iconic 333 W. Wacker Drive, a curved, blue-green glass building that contours the short stretch where the river turns from west to south on its way to Lake Michigan. When I was 23, a friend and I overpaid rent for an office at 333 where we sold ad specialties. Twenty years and two careers later, I was back in the same building running a Chicago mayoral race.
I walk six blocks east on Lake Street and hit famed State Street. Steps from the corner sits the Chicago Theater, built over a century ago and the venue for some of the most historic acts in America. Seeing Bob Dylan for the first time was the highlight for me.
Straight across the street sits WLS-TV, the third oldest ABC station in the U.S., built over 75 years ago. As a 19-year-old student at Indiana, I thought my dream had come true when I landed a sports internship at ABC-7 News. I was as happy logging sports highlights for anchors Tim Weigel and Jim Rose as I was when Jim drove me to Wrigley Field on the night they first turned the lights on.
Two decades later, I’d be sitting in the same rooms at ABC-7, preparing congressional candidates for live debates.
If you walk back to Lake Street and drive four miles west, you’re at the “United Center” (an unfortunate name for what will always be the Chicago Stadium). When I was 13, Lake Street was the route my Dad took when he drove us to Bulls games. It was also, along with Lower Wacker Drive just underneath it, where the city gave director John Landis permission to let “Jake” and “Elwood” (and Chicago Police squad cars) race at over 100 mph in The Blues Brothers.
Ten years later, at 23, I would drive down Lake Street three nights a week to the Stadium. A lucky break landed me as a reporter for “The Sports Spotlight” on SportsChannel. Before and after Bulls and Blackhawks games, I’d be in the locker room interviewing future Hall of Famers. It was heaven. A year later, I started two radio shows, “Bull Session” and “Hawks Weekly,” and the Stadium became like a second home.
If you walk back east to the Chicago Loop, you can hop on a riverboat and cruise the waters they dye green(er) every St. Patty’s Day. I still take the tour every year or two, and yesterday’s ride was every bit as enjoyable as my maiden voyage. Civic Opera on your right, Mercantile Exchange on your left (where I was also an intern), Marina City, the Merchandise Mart, the Vietnam Memorial, the Willis (Sears) Tower… Take the cruise if you ever come to Chi. Trust me.
But my favorite spot on it is where the boat docks at: the intersection of Michigan Avenue and Upper Wacker Drive. This is where One Mag Mile starts, though that’s not the attraction. I love the end of the tour because that’s where I can see both the historic Wrigley Building and old Chicago Tribune Tower — right across from one another on the Ave.
I remember sitting outside on an office patio in Trib Tower, where my friend Doug had started a radio sales job. We were in our early 20s and it was a Friday night. We looked out at the city with a sense of awe, yet at the same time confidence: We’re gonna do things here.
So many years later, after I wrote Unlock Congress, I would do live shots as a political analyst for WGN-TV in its remote downtown studio inside Trib Tower. And on Sundays, Chicago Tribune political writer Rick Pearson would have me on his WGN-AM show — beamed out live from the ground floor studio along Michigan Ave. Folks would wave and gesture from outside as they watched and listened to us. It was so very Chicago.
When I was a kid, the word “Wrigley” meant nothing more to me than the name of my Dad’s Doublemint gum. Just six years ago, thanks to a friend and Chicago PR legend, Carolyn Grisko, I would run my own consulting business from an office inside the North Tower of the famous Wrigley Building. How things come around.
Plenty of folks assume Chicago gets its “Windy City” moniker from its wild weather. But the city is far too colorful for that; the nickname derives from the infamously hot air belched from the mouths of Chicago politicians. When you hear the name Daley, you think Chicago. But so many other names instantly attach: Payton and Sayers, Uno and Due, Ness and Capone, Jordan and Pippen, Winfrey and Donahue, Siskel and Ebert, Royko and Mamet, Lolla and the “L,” Bueller and Belushi… I’d better stop.
You just can’t go to any section of the city and not be blown away by the history. When I arrived downtown on Thursday to stay at my friend Michelle’s condo along Lake Shore Drive, I was instantly reminded that it used to be the old “New” Playboy Building. And on the first floor, you can still see the original window art from the famous old Gold Star Sardine Bar — the place where names like Minnelli, Bennett, Basie and Getz played exclusively when they came to town.
The reason I’m in Chicago this weekend is to attend the Degrees of Impact Gala to raise funding for community college students. One Million Degrees is a scholarship program that a handful of us created almost 20 years ago, and it feels like we’ve staged the event in just about every neighborhood in the city. But last night, several hundred of us convened at a beautiful new complex in Lincoln Yards, that runs right along the river in West Town.
We all had a blast. It’s hard not to in Chicago.
you are an amazing storyteller. my suggestion? we start a podcast. two jews in the desert
Makes me want to drive to Chicago and sit at Wolf Point. The story of the Gold Star Sardine Bar is fascinating.