Jessie Maynard (September 4, 1894 - August 13, 1976) was born in Williamson, the daughter of Ira and Emily Butcher Maynard. She was a niece of Randolph and Sarah McCoy of Hatfield-McCoy fame. Little is known about her early life other than she attended school in 1904-05 in Naugatuck, Mingo County.

On September 6, 1911, she married Cabell C. Testerman, a jeweler and optician who had moved to Matewan from Wyoming County. Both of Testerman's first two marriages—to Donna Anderson (1900) and Lula Minton (1904)—had ended in divorce. The couple took up residence in Matewan and, in September 1916, adopted Walter Hight, who had been born the previous year in Charleston. They named him Jack.

On May 19, 1920, Cabell Testerman—by this time mayor of Matewan—was one of the first people wounded in Matewan during a shootout between townspeople who supported the United Mine Workers of America and Baldwin-Felts detectives who had been evicting striking miners from company-owned houses. At the very beginning of the fight, Testerman was shot in front of Chambers Hardware store. He died that evening in Welch. In the flurry of gunfire, it is unclear who killed Testerman. Unsubstantiated rumors circulated immediately—and ever since—that Testerman had been shot at point-blank range by town police chief Sid Hatfield, who likewise supported the striking miners. Others strongly defended Hatfield, particularly at the subsequent trial, where several witnesses claimed they saw Tom Felts, a partner in the detective agency, shoot Testerman.

Less than two weeks later, on June 1, Hatfield and Jessie Maynard Testerman boarded a Norfolk & Western train to wed in Huntington. After getting their marriage license, they checked into the Florentine Hotel, where they were visited by Huntington police officers Lt. J. M. Messenger and Detective A. H. Vernatt. Tom Felts, whose brothers had been killed at Matewan, supposedly tipped off the police about the couple's whereabouts. Hatfield and Testerman were arrested and jailed overnight for cohabiting while unmarried and committing adultery. During a five-minute trial the next morning, Judge Newman of the Huntington Police Court fined them $10 but dismissed the penalty after learning of their imminent wedding plans.

As Hatfield and Testerman emerged from the courthouse, a photographer from the Huntington Advertiser snapped their photo. Their next stop was the city's First Presbyterian Church, where they were married. The quick wedding added more fuel to rumors Hatfield had killed his bride's late husband. When questioned, Hatfield insisted that "Testerman had been his best friend and that he had pulled his gun in Testerman's defense when the detectives began shooting." The day after the wedding, the Williamson Daily News halfheartedly came to Hatfield's defense, writing that he had been "proven guilty of nothing more than a breach of good taste. In view of this fact we can only suggest that 'the less said about it, the better.'"

During their short marriage, the couple and young Jack Testerman lived in a Matewan apartment. On August 1, 1921, Hatfield was assassinated, with his wife at his side, by C. E. Lively and other Baldwin-Felts agents as he ascended the McDowell County Courthouse steps in Welch. In a brief time, Jessie Maynard Testerman Hatfield had been widowed twice as a result of public shootings in broad daylight directly related to the West Virginia Mine Wars. Hatfield's murder sparked the Miners' March on Logan and the Battle of Blair Mountain. On October 28, 1921, Jessie, accompanied by Sallie Chambers—whose husband had been murdered alongside Hatfield—testified in Washington, D.C., before a congressional subcommittee on violence in southern West Virginia.

Reeling from the turmoil and the loss of two husbands in less than 15 months, Jessie married State Trooper Sylvester Pettry on January 31, 1922. A World War I veteran, Pettry had joined the State Police, which had been established in 1919 to help combat labor unrest in the southern West Virginia coalfields. They divorced within a few years. On July 9, 1928, she married another World War I vet, Wilson R. Jennings, in Ironton, Ohio. During the Great Depression, they moved around frequently as Jennings worked in different railroad jobs. In the 1930 census, they showed up, with Jack, in Montgomery, Alabama. That same year, she filed for divorce from Jennings but never finalized the proceedings.

On June 9, 1932, Jennings and another man, Lawrence Piercy, robbed the National Bank of Paintsville, Kentucky, of $47,000. The two were convicted and sentenced to 20 years in prison, although both were out on parole by 1935. On December 15 of that year, Hobert Meade, the Paintsville bank clerk who had testified in Jennings' and Piercy's trials, was shot and killed. In June 1937, Jennings and Jessie were arrested for Meade's murder. At the time, Jessie was living with her parents and sister Zettie in Naugatuck, supposedly estranged from Jennings. After spending a brief time in jail, the charges against both were dropped.

The couple, back together, moved to Lawrence County, Ohio, where they lived the rest of their lives. She died at Ironton's Lawrence County General Hospital at age 81. Jennings died in 1988. Jessie's only son, Jack Testerman, died on January 31, 2001.