President of the United States
Executive producer, Check, Please!
When Manilow needed guests in the show’s early days, he tapped Barack, then a “lively, articulate” state senator, who taped an episode in 2001.
Host, Check, Please!
She wasn’t hosting when Barack appeared—and has never met him—but she asked the president back for the show’s tenth anniversary. He declined.
Author and Lab Schools alum
Singh’s husband is a childhood friend and University of Chicago Lab Schools classmate of Chris Grimshaw’s.
Singer/songwriter, owner of Real Time Learning tutoring
Robbins met Blackstone and Chris Grimshaw in high school. She attended the Grimshaws’ goodbye party when they sold their Greenwood Avenue home.
Catering company co-owner and Lab Schools alum
This resident of Austin, Texas, is the son of Bill and Jacky Grimshaw, the First Family’s former Hyde Park neighbors.
General counsel, U.S. Department of Transportation
Director, President’s Commission on White House Fellowship
These former Chicagoans, who are husband and wife, introduced Barack to their friend David Manilow in the late 1990s. A former assistant to Mayor Richard M. Daley, Moelis worked with Michelle in City Hall in the early 1990s.
Civil rights leader
The late activist, after whom Al Raby High School is named, introduced Barack to Jacky Grimshaw to get her opinion of the young organizer.
Vice president of the Center for Neighborhood Technology and CTA board member
A former adviser to Harold Washington, Grimshaw met Barack when he was a community organizer, years before he moved in next door.
Oregon State basketball coach and Princeton alum
The First Lady’s older brother befriended Vietta Johnson at Princeton.
Owner, Naturally Fit
The West Loop gym owner has been the Obamas’ trainer for more than a decade and serves on the President’s Council on Fitness, Sports, and Nutrition.
Owner, Kozan Design Studios
Works out at Naturally Fit. When she was having trouble with nightclubs near her West Loop–based business, Barack, then a U.S. senator, offered her advice.
Working election day 2008 to decorate the salon for the big party, Shores-Navata hung a picture she painted of Barack getting his hair cut by Zariff.
Barber, Hyde Park Hair Salon
Zariff has been cutting Barack’s hair for almost two decades.
Former head of orthopedic surgery at Providence Hospital and Princeton alum
A college friend of Robinson’s, she used to bring him home to Brooklyn on school breaks. Met Michelle at Princeton; later met Barack at McClellan’s gym.
Former CPS superintendent
Johnson met Robinson when her daughter, Vietta, brought him home during school breaks. She met Barack later, when he came to Chicago as a community activist. They both worked out at McClellan’s gym.
KEITH ANN STIVERSON
Director, IIT downtown campus library
Stiverson went to Naturally Fit years back and recently returned with encouragement from Kozan, whom she met through her neighborhood Chicago Police Department District Advisory Committee.
Five years old
The artist’s daughter chatted about school with Barack in the salon a few days before the election.
Store associate, Walmart
Wanaki’s mother (Zoe’s grandmother), Taylor likes to tell co-workers and shoppers about her daughter’s painting of the president.
Photography: (Barack Obama) Jack Dempsey/AP; (Manilow) Ryan Robinson; (Singh) Alex Garcia/Chicago Tribune; (Blackstone) N. J. Mulroney; (Robbins) Lenny Gilmore; (Chris Grimshaw) Corey Nicolas Critser; (Jacky Grimshaw) James Warden/Five Lake Arts; (Raby) Chicago Tribune; (Moelis) Marc Harris; (Robinson) Penguin Books; (Michelle Obama) Heather Charles/Chicago Tribune; (McClellan) Cathy Brown/HHS; (Zariff) Jose More/Chicago Tribune