Stokes was one of ten siblings. He left school after completing the eighth grade.

On April 30, 1969, Stokes committed his first documented crime. Along with David H. Richards (17) and Allen E. Smith (18), he entered a tavern at 3044 Easton Avenue in St. Louis, pretending to be a customer. After drawing their pistols, they announced a robbery. The patrons and the owner, Ignatius DiManuele, were forced to lie on the floor while the robbers emptied the cash register. During the robbery, one of them shot DiManuele, explaining it was because he "wanted to get a whitey." The trio fled in Stokes' vehicle. Two weeks later, Detectives Brian Graft and Edward DeVere stopped Stokes for questioning, during which he discarded a pistol from his car. This led to his arrest, and after interrogation, Richards and Smith were also apprehended. Witnesses identified them as the perpetrators of the robbery and shooting.

Stokes was detained at Homer G. Phillips Hospital to await trial. Several months later, he escaped with four other inmates. On October 23, 1970, when Sheriff's Deputy John Curtis entered the ward, Stokes grabbed his revolver, forced him to strip, tied him up with pieces of a bedsheet, and fled with the others. Three of the escapees were later recaptured, but Stokes and 18-year-old Joseph Wallace evaded capture. Stokes was eventually arrested again and sentenced to nine years for manslaughter and other felony charges.

After serving his sentence, Stokes was released. On December 7, 1977, he attacked 71-year-old Erssie Lucas with a claw hammer during a robbery, leaving Lucas injured but alive. Five days later, on December 12, Stokes broke into the apartment of 73-year-old widow Marie Montgomery, shot her in the neck and arm, and stole a wristwatch. Montgomery's body was discovered by her niece after she missed a church service. Stokes was arrested on January 15, 1978, for armed robbery and criminal action but managed to escape from the Malcolm Bliss Mental Health Center that afternoon.

On February 21, 1978, Stokes met 33-year-old Pamela Benda at a bar in northern St. Louis County. They went to her apartment in University City, where he beat, stabbed, and strangled her. He then stole jewelry and fled in her 1974 Plymouth Scamp to South Bend, Indiana, where he lived with his wife. Initial investigations focused on Benda's boyfriend, but he was later cleared. It was determined that Benda likely knew her killer, as there were no signs of forced entry. The case was dubbed the "Mr. Goodbar" case, referencing a novel found at the scene.

In June, Stokes was indicted for the murders of Montgomery and Benda. He was again sent to Homer G. Phillips Hospital to await trial. On December 3, along with Samuel Smith and Earl Davis, he overpowered guards, stole their guns and clothes, and escaped. One guard, Richard Campbell, resigned the next day. All three fugitives were arrested by FBI agents on December 11 in Chicago's South Side.

On September 10, 1979, Stokes pleaded guilty to second-degree murder for Montgomery's killing and received a 50-year sentence. He was offered a concurrent 50-year sentence for Benda's murder if he pleaded guilty but opted for a trial, facing possible execution. Prosecutor John Walsh presented evidence, including fingerprints and Montgomery's wristwatch found at a pawn shop. On October 24, Stokes was found guilty of capital murder for Benda's death.

During sentencing, Stokes' attorney, John T. McCaffrey, argued that an all-white jury was biased. Prosecutor Walsh highlighted Stokes' violent history. The jury recommended a death sentence, and Justice John R. Rickhoff sentenced Stokes to die in the gas chamber. Scheduled for October 28, 1982, the execution was temporarily stayed by U.S. Supreme Court Justice Harry A. Blackmun. The full Supreme Court later denied Stokes' appeal. Six years later, a federal appellate court rejected his final appeal. On May 11, 1990, Winford Stokes was executed by lethal injection at the Potosi Correctional Center without making a final statement.