Dick Bayless – Howell County Professional Bank Robber

A popular student, successful in three high school sports, Dick Bayless had a lot going for him despite his facing numerous adversities in life. From a home broken by divorce in Wichita, Kansas, where both parents were living, he was sent at the age of sixteen to live with his grandmother (some accounts say aunt) in the Ozarks. There, he was raised on her farm, located north of Willow Springs in the Sterling community. The Great Depression in the rural Ozarks was tough on everyone, especially John Richard “Dick” Bayless, who felt he needed to relieve his grandmother of the burden of supporting him. He attended Willow Springs High School, was a good student, and had a passion for science.

 

In his senior year, 1932-1933, he lettered in football, basketball, track, and tennis for the Bears. He played in the band and the school orchestra, was a member of the glee club, and starred in several high school plays. Dick must have been quite a talker. The “Williamizzou” yearbook used this line from the Shakespeare poem Venus and Adonis to describe him and caption his student photo: “Bid me discourse; I will enchant thine ear.” Earlier in 1933, before graduation, his name appeared in the Willow Springs News, reporting that he had attended services and youth social activities at the First Baptist Church in Willow Springs every Sunday.

 

Graduating Willow Springs High School in May 1933 Dick Bayless joined the United States Navy. He was trained as an aircraft mechanic on the aircraft carrier USS Saratoga and was based at Long Beach, California. He hated military life and, in July 1935, deserted. He put a payment down on a 1931 Ford roadster and drove cross-country to Willow Springs. He caught the attention of local law enforcement officials when he forged a small check on his grandmother’s signature. Deputy Wade Belshe and State Troopers Ben Graham and Ted Taylor conducted an investigation. They discovered that Bayless was wanted for auto theft and issuing bad checks in California, and subsequently arrested him. 

 

Because the car he took was driven across state lines, the charges were federal. In December 1935, Bayless was tried and sentenced to two years in the United States Reformatory in El Reno, Oklahoma. A short time after serving his sentence, Bayless met and married an attractive young woman named Gwendolyn Lee Bailey in Kansas City and made a stab at domestic life. Refusing to work, his new bride, noticed Dick always had money, would leave with friends all day, and never reveal his activities. He finally lied and told her he had received money from an inheritance and would be receiving a lot more.

 

Only weeks into their marriage at the end of October 1937, the newlyweds, accompanied by Dick’s friend and criminal partner, Richard Simms, and his wife, Orletta, went on a couple's trip to see Gwendolyn’s mother. Driving from Kansas City to Wichita, Kansas, Bayless handed the car over to Simms, who, driving recklessly, lost control, rolled the vehicle several times, and landed it upside down in a ditch. Dick and Gwendolyn in the backseat were pinned under the car. Dick managed to crawl out with a cut on his arm, but his new wife was critically injured with a neck fracture and broken femur in her leg, entailing an extended hospital stay. Dick Bayless then decided to return home and “get some money.” A short time before the wreck Gwendolyn accidentally discovered a pistol in Dick’s coat pocket when she sat on it. It was dawning on her that there was more to her husband’s story than he was telling her.

 

Bayless was already on the FBI’s watch list, and a local paper published an article on the wreck, leading them to interview Gwendolyn in her hospital bed. Their interest in Bayless stemmed from a bank robbery at The Merchants Bank in Mansfield, Missouri, that had occurred a day earlier. The bank was robbed by two men in coveralls with drawn pistols who fit the description of Bayless and Sims. With this information, agents immediately headed to Sim’s residence and found both men in bed asleep and arrested them. Bayless commented, “You caught me asleep, copper, or I’d have blasted you.” 

 

Bayless had spent a night in Willow Springs, visiting with high school friends before committing the robbery. He stole a car belonging to West Plains Theater owner Dean Davis to use in the commission of the crime. Davis later corresponded with Bayless in prison to retrieve a camp stove of sentimental value that had been in the vehicle when it was stolen and discarded at a remote location in the woods. Davis was amazed by Bayless’s knowledge of the rural roads that took him directly to his stove.

 

Despite their modest take of slightly above five hundred dollars, the severity of the case was heightened by their additional crimes. They locked the female bank tellers in the vault, constituting a kidnapping charge, and they targeted a bank with FDIC insurance. Both men pleaded guilty and, in February 1938, were sentenced in Kansas City to twenty-five years in federal prison. Sim’s wife was also arrested based on some eyewitness reports that a third individual dressed in coveralls was seen at the robbery. Gwendolyn was hospitalized at the time of the robbery, and investigators deemed that she was unaware of her husband’s criminal activities.

 

Bayless arrived at Leavenworth in February 1938 and, in November of the same year, was transferred to Alcatraz Prison. There, he appeared to be a model prisoner, a loner who spent most of his free time alone. Bayless was assigned to the prison garbage detail, a good assignment that allowed him to walk around the entire island. In September 1941, in the fog that often surrounds Alcatraz, Bayless, at the end of his shift, made a snap decision to escape. Just before the prisoners on the detail assembled to be marched back to the cell house, Bayless slipped off into the fog and jumped to the rocky shore. 

 

At that moment, a guard noted he was missing, and klaxon alarms sounded all over the island. Bayless stripped to his pants and went into the water, and later told authorities that once he was chest high, he found the water so cold he had trouble staying afloat. The guard who alerted the prison that he was missing spotted him in the water and took him back to the prison hospital, suffering hypothermia and disoriented after being in the water for only five minutes. When asked why he tried such a foolhardy thing, Bayless responded that he was depressed.

 

On trial in January 1943 for the escape attempt, Bayless broke from his guards in court in another escape attempt and was tackled and sent back into solitary confinement. He was sentenced soon after to another thirty years in federal prison. There, Bayless behaved and earned a transfer back to Leavenworth prison in 1950. In August 1951, he was granted conditional parole, but it took him only three months to commit another bank robbery - one that gained national attention.

 

In February 1952, Bayless robbed a bank in Hollywood, California, netting over nineteen thousand dollars in cash, the equivalent of nearly half a million dollars today. He boarded a flight bound for New York, and his three-thousand-mile escape attempt made the national news in the early days of air travel. When he exited the plane, FBI agents wearing airline maintenance clothing walked up to Bayless from behind and grabbed his arms, thwarting his attempt to pull a pistol from his belt.  He was carrying the proceeds from the robbery, including marked money, in a satchel. In addition to bank robbery charges, he was also charged with violating his parole from Leavenworth. 

 

So one year after his release, Bayless found himself back on Alcatraz to begin a thirty-five-year sentence. He would be among the last inmates to leave Alcatraz when it closed in March 1963. Bayless was sent to the McNeil Island Correctional Center in the state of Washington, where he and a fellow inmate soon jumped a guard using a knife they had made and attempted escape. Still on the prison grounds after escaping the cellblocks, they found the vacant house of the prison physician who was away on a hunting trip. The physician, upon returning home, noticed it was occupied and alerted the guards. The two escapees surrendered without incident. Another forty-five years were added to Bayless’ sentence. 

 

In August 1973, he was again paroled, and just one month later, he attempted to rob another bank and was taken back to Leavenworth. Bayless was paroled to a community treatment center in Long Beach, California, and died there in July 1981. He is buried in Lake Elsinore Cemetery, Riverside County, California.

 

Bayless was not any good at robbing banks. It is hard to understand why he persisted in this line of work. Howell County officers in 1952 were quoted as describing Bayless as a “very shrewd fellow.” As a side note, he did have skills. While imprisoned, Bayless became an accomplished self-taught lawyer and successfully filed his own appeal for a new trial in the California bank robbery case. He was subsequently convicted a second time. Dick Bayless also became an expert in making jelly rolls and lady fingers in the prison kitchen.