12/10/2025
Here are ten interesting and lesser-known facts about Barack Obama's time and enduring legacy in Chicago:
His first date with Michelle ended with an ice cream kiss. The couple's first date in the summer of 1989 included a stop at a Baskin-Robbins in the Hyde Park neighborhood. The spot is now marked by a plaque and a large boulder known as the "Obama Kissing Rock".
Michelle was initially his mentor. When Obama joined the Chicago law firm Sidley Austin as a summer associate in 1989, his future wife, Michelle Robinson, was a young lawyer assigned to supervise his work.
He disliked ice cream due to a teenage job. Despite the iconic first-date spot, Obama is reportedly not a fan of ice cream, a dislike stemming from his experience working at a Baskin-Robbins as a teenager in Hawaii.
He taught law at the University of Chicago for 12 years. From 1992 until his election to the U.S. Senate in 2004, Obama was a lecturer (and later a professor) on the faculty of the University of Chicago Law School.
He lost his first congressional race badly. In 2000, Obama ran for the U.S. House of Representatives seat in Illinois's 1st district but lost the Democratic primary to the incumbent Bobby Rush by a significant margin.
He was a competitive pick-up basketball player. In his younger days in Chicago, Obama frequently played pick-up basketball games at a court near the lakefront and was known for actively participating in the competitive banter.
His longtime barber flew to D.C. for his haircuts. For about 20 years, Obama's primary barber was Zariff, whose shop, the Hyde Park Hair Salon, was a local hub for community debates. Zariff continued to cut his hair even during the presidency, flying back and forth from Chicago to Washington.
He began his career as a community organizer, calling it his "best education." After college, from 1985 to 1988, Obama worked as the executive director of the Developing Communities Project (DCP) in the Roseland neighborhood, a period he credits as the most formative of his education.
The construction of the Obama Presidential Center will close a major street. To create a single, contiguous green space for the future Obama Presidential Center, the city plans to close a section of Cornell Drive, a move designed to better connect the center to the surrounding community and other nearby museums.
His Chicago home is heavily guarded and mostly obstructed from public view. The Obamas' home in the Kenwood neighborhood is a private residence protected by the Secret Service, and evergreen trees largely block the view from the street, preventing drive-bys or photos.
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