Meanwhile, Sam’s luck was going from bad to worse. Discovered by Willie Dixon, the main songwriter for Chess Records, Sam was passed over by the Chess brothers, who didn’t know what to make of his sound. He found a home at the Cobra label, founded by small-time professional gambler Eli Toscano. Playing off of “Maghett,” Toscano christened his new artist Magic Sam, and recorded him fast and quick, capturing the energy of Sam’s live performances. At Cobra, Sam recorded the foundation of his legacy—11 blazing singles and b-sides, including the classic “Everything Gonna Be Alright,” the lightning-fast, proto-rockabilly “21 Days in Jail,” and the ironic “Out of Bad Luck.” (I’ve been down so long, Sam cries. But I am on my way back up again.)

In fact, Sam’s bad luck was just beginning. The Cobra singles lit up Chicago, but failed to find an audience outside the city. Still, momentum was building in the last years of the 1950s. But as word started to spread about Sam, he was hit by two devastating blows: Cobra folded and he was drafted. Within weeks, Sam went AWOL from the Army to record for Chief Records. The Army caught up with him, and sent him to prison for deserting. The sentence took its toll on Sam emotionally, and when he was released in 1960, rock ’n’ roll’s popularity had taken a toll on the Chicago blues scene. It was before the mid-60s folk revival—which would pass up Sam in favor of more acoustic artists—and good gigs were scarce. Sam struggled for years.

Enter Bob Koester. The founder of the legendary Delmark label, Koester is an unsung hero of the blues in his own right, and as tough and passionate as the artists he has recorded. Riding high on the unexpected success of Junior Wells’ masterpiece Hoodoo Man Blues—featuring West Side-style guitar workouts by Buddy Guy, credited as Friendly Chap to avoid label conflicts—Koester recognized Sam’s brilliance instantly. “I first heard Magic Sam on one of the great Cobra 45s,” Koester recollects in the liner notes of the Delmark release The Magic Sam Legacy. “Later, in person at the original Alex Club at Roosevelt and Loomis on Chicago’s West Side in 1962. It was a spectacular entrance—Muddy Waters called him up to the bandstand. Sam tripped on an electric cord and sparks flew! His playing and singing were even more electrifying.”

Sam reestablished his reputation in Chicago through relentless, grueling nightclub shows, but it was an uphill battle. He was constantly hounded by the union, and exploited and ripped off by shady management. Guided and supported by Koester, Sam recorded the flawless West Side Soul for Delmark. Backed by the great Mighty Joe Young on second guitar and Odie Payne on drums, Sam poured his heart and soul into some of the most powerful blues ever recorded. From the soul swing of “That’s All I Need” to the chilling “My Love Will Never Die,” West Side Soul is an artistic triumph. The album received glowing reviews in national press. Cream, Canned Heat, Paul Butterfield, John Mayall, and Janis Joplin had prepared the public’s ears for raw blues, and for a moment it looked like Sam’s time had come. Delmark’s distribution was getting stronger, and Sam was earning invitations to large festival gigs around the country. He was plagued with bad management, though, and suffered a gun shot wound to the leg that left him performing his Los Angeles debut in a full cast.

Sam persevered, though, and performed a now-legendary set with Charlie Musselwhite at the 1969 Ann Arbor Blues Festival. He returned to the studio and cut the incredible follow-up Black Magic for Delmark. Sam not only felt it was the best album he had ever done, he called it “the best album I’ve heard.” He was not alone—the two Delmark releases were cementing Sam’s reputation as one of the true blues greats. Wishing him the best, Koester made plans to release Sam from his contract with Delmark so he could record for Stax. It seemed the world was finally ready for the powerful sounds of Magic Sam.

Sadly, on the morning of December 1, 1969, Sam complained of pain in his heart, and collapsed on his way to his bedroom. He was rushed to a Chicago hospital, where he was pronounced dead on arrival. He was 32.

In the years since, Koester and Delmark have painstakingly preserved Sam’s legacy. Three must-have releases—West Side Soul, Black Magic, and The Magic Sam Legacy—offer a hint of Sam’s stunning talent, and a glimpse of what might have been.