Review: Windy City Blues Layers Love and Politics Over the Early Days of Chicago Electric Blues

Note: Windy City Blues has been selected by Spertus Institute for its One Book One Community book of the year. Spertus has several events planned around Rosen’s book. If you love Chicago electric blues, you have two ways to learn more about their origin. You can read one of the music histories of the period (more on those later), or you can read a new novel by a Chicago writer that blends historic facts and folks with a fictional romance about an interracial couple in the 1950s. The very readable novel is Windy City Blues by Renée Rosen, whose several novels combine Chicago’s rich cultural history with storytelling. The storytelling in this case is the tentative and then intense romance between Leeba Groski, a songwriter from an orthodox Jewish family, and a tall African-American guitar player from New Orleans named Red Dupree. Leeba gets an office job at Chess Records, operated by her neighbor Leonard Chess and his brother Phil. Leonard and Phil operate a black blues club called the Macomba Lounge on South Cottage Grove Avenue, a late night venue. Just when the brothers are desperate for funding for their new record business and frustrated over the brawls and property damage at the club, the Macomba burns to the ground. Phil, the practical man, had bought insurance to cover their operations and Chess Records is born. I’ve read quite a bit about this period of Chicago blues and Chess Records; the basic facts about the Chess brothers and their company in Windy City Blues are accurate. Real-life characters like musicians Muddy Waters, Sunnyland Slim, Willie Dixon, Little Walter, Bo Diddley and Chuck Berry are portrayed and so is Evelyn Aron, Leonard’s partner at Aristocrat Records, the company he buys out to form Chess Records. Also accurate is the description of Leonard’s method of boosting record sales by traveling around the country with a trunkful of records to visit store owners and radio stations. He wasn’t above including a folded $20 bill when he handed the record to a station manager or DJ. Phil stays at home and takes care of operations and finances. Leonard also has an ear for what will sell as the new race music, which is just becoming popular with a white audience (and especially with British music lovers). Chicago has black and tan clubs, where white music lovers mingle with black fans and musicians. And that’s where Leeba and Red have their first date—at a black and tan club—because it’s the only place where they can be together, other than in Red’s kitchenette apartment. Red’s goal is to be a successful musician and give up his job at the brickyard. When he first arrives in Chicago, he meets Little Walter, the brilliant harp (harmonica) player and they play together for tips every weekend in what’s known as Jewtown on Maxwell Street. Red writes music and they audition for Leonard Chess but are rejected several times. Finally, they’re both asked to play in Muddy’s band and Red has a chance to watch the master guitarist and frontman and refine and develop his own style. Meanwhile Leeba, now known as Leah, is developing as a songwriter, writing heartfelt songs for her friend Aileen, a promising singer who has drug and alcohol problems and an unfortunate affection for Muddy, a man who loves many women. Leah and Red become politically active in the civil rights movement of the 1960s. They join the Freedom Riders in the South and Red becomes a spokesman for the movement in Chicago. Author's photo by Charles Osgood. The story of Leah and Red is overlaid on the changes in the music business that affect the Chess brothers and their company. Race music becomes the blues and then rock and roll. The payola scandal touches some of Leonard’s DJ friends like Alan Freed. British musicians tour the U.S. and Muddy Waters takes his first airplane ride to London, where he’s greeted as a hero. Rosen tells the story of the Rolling Stones’ first visit to Chicago. Upon arriving at O’Hare, they jump in a taxi and go straight to 2120 S. Michigan, where they record an album titled 2120 South Michigan Avenue in June 1964. They record two more albums at Chess Records in 1964-65. Author Rosen tells a good story; Windy City Blues is a page-turner. She includes an author’s note where she explains some literary license she took with the historical facts of the era when the Mississippi Delta blues came to Chicago. She explains how she compressed some events and timelines, and substituted a character or two. She also provides a bibliography of books, documentaries and films that provided background material. If you’d like to read more about the era of Chess Records, I recommend Nadine Cahodas’ Spinning Blues Into Gold: The Chess Brothers and the Legendary Chess Records (St. Martin’s Press, 2000). There’s also The Record Men: The Chess Brothers and the Birth of Rock and Roll, by Glencoe native Rich Cohen (W.W. Norton, 2005). Cohen’s book is very readable, but Cahodas’ book is a more detailed history. Both authors describe the problems with royalty payments and the way the black musicians were treated by Chess Records. You can buy Windy City Blues (Berkley/Penguin Random House, 2017, 456 pages) at bookstores and online for $16 (paperback) or $10 (ebook).
Picture of the author
Nancy S Bishop

Nancy S. Bishop is publisher and Stages editor of Third Coast Review. She’s a member of the American Theatre Critics Association and a 2014 Fellow of the National Critics Institute at the Eugene O’Neill Theater Center. You can read her personal writing on pop culture at, and follow her on Twitter @nsbishop. She also writes about film, books, art, architecture and design.