If you’ve ever read a list of “17 celebrities you didn’t know were from Milwaukee,” you know that Oprah Winfrey is kinda-sorta from Milwaukee. Born in Mississippi but raised in Milwaukee by her mother, Vernita Lee, Oprah still has family in the city to this day. And she’s not adverse to visiting them: Over the weekend, for instance, Oprah (and Stedman!) were spotted in the audience at the University of Wisconsin-Milwaukee’s graduation ceremony. Oprah’s half sister, Patricia Lee, was one of the graduates.

“Soon after the commencement ceremony began at the UW-Milwaukee Panther arena, posts and pictures showed up on Twitter about the media mogul’s presence,” reported the Milwaukee Journal Sentinel. “They were all probably hoping she was there to give out free cars.”

The Journal Sentinel added: “In the pictures, the couple are sitting in the crowd reading their programs, just like everyone else.”

Cool! In that spirit, here’s a brief history of past Oprah sightings (and half-sightings) in Milwaukee, and the breathless media reports that chronicled them.

February 28, 2008: “Will Oprah give big in Milwaukee?” (OnMilwaukee)
“I caught an episode of ‘The Oprah Winfrey Show’ this week where Winfrey interviewed Henry ‘The Fonz’ Winkler.” So begins this 2008 OnMilwaukee piece from Molly Snyder, which wonders whether Oprah will bring her “Oprah’s Big Give” show to Milwaukee. Turns out, she didn’t. (And she didn’t even ask Winkler about the Bronze Fonz!)

February 19, 2011: “Oprah Winfrey stops in Third Ward, dines at Swig” (OnMilwaukee)
The “Oprah spotted in Milwaukee” story that all others shall be judged against, now and forevermore. OnMilwaukee scribe Jeff Sherman lays out a detailed, paparazzi-esque account of Oprah, her half sister, and “several others” eating food at Swig. Did the group sit at a front window table? They did. Were they observed “talking, asking customers for recommendations, and taking in the Downtown neighborhood scenery”? They were. Was Sherman’s wife tangentially involved in the encounter? Of course.

Winfrey, wearing a fashionable off-white (my wife called it “winter white”) outfit, left the restaurant at about 6 p.m. laughing, talking and even hugging people on the sidewalk. The entire group had to-go boxes with them.

My wife, who works down the street at Lela, helped Winfrey’s driver navigate into the parking lot next to Swig as he picked up the group.

September 1, 2015: “Oprah pop-up store appears in Milwaukee” (WISN)
Some people have rummage sales; Oprah has pop-up events in haunted Milwaukee hotels. Back in 2015, more than 400 designer clothing items belonging to Oprah went up for sale at the Pfister Hotel, with all proceeds going to charity. Sadly, Oprah didn’t attend the Pfister event, probably because of Joey Lawrence.

November 20, 2016: “Oprah Winfrey in Milwaukee for Thanksgiving?” (TMJ4)
Was Oprah in Milwaukee for Thanksgiving 2016? Well, according to an Instagram post from Oprah that was hashtagged #Milwaukee, the answer was “YES, OF COURSE SHE WAS.” Hats off to TMJ4 for subverting Betteridge’s law of headlines.

November 18, 2017: “Oprah in Milwaukee?” (Reddit)
“My partner was just at the Whole Foods on Prospect and is convinced he saw Oprah there,” reports Redditor deletedmyoldaccount_. “He also said he overheard two employees talking about it being her.” Yep, that was probably Oprah. You see, she’s from Milwaukee. And she has family here. Oprah.

About The Author

Matt Wild
Co-Founder and Editor

Matt Wild weighs between 140 and 145 pounds. He lives on Milwaukee's East Side.