Anna Benson was born outside of Atlanta, Georgia on February 12, 1976. (Benson, who calls herself a "harlot," says of people in her native state "They're so judgmental. It’s real Bible Belt.") A self-described "lonely latchkey kid," Benson dropped out of school following her sophomore year of high school, and left home when she was sixteen.Subsequently, she says, “I was a dancer in the Atlanta strip clubs.... I had a baby and then a husband when I was seventeen." In 1998, she met her future husband, Kris, while she was dancing at the Mardi Gras, a strip club in Atlanta, when he was playing for the Nashville Sounds in the minor leagues.(They had attended rival high schools in Georgia, but had never gotten to know one another prior to this meeting.) She and Kris Benson were married in October 1999 (her second marriage, his first). The Bensons were soon labeled "baseball's most incongruous couple," with Anna having "diverted attention" from a star pitcher who "often fades into the periphery." Anna filed for divorce on March 31, 2006, citing an "irretrievably broken" marriage. Anna Benson—who commented, "when I came to Kris, I had nothing—two pairs of panties and one bra; suddenly, I found I was married to a millionaire". She later withdrew the petition, and subsequently has had another child with Kris. Altogether, they are raising four children: her daughter Alyssa (from a previous marriage), their daughter Haylee, and sons P.J. (from "Paul James") and Devin. As of 19 July 2012 Kris has served Anna with divorce papers.
On July 30, 2004, the Pirates traded Kris Benson to the New York Mets. In November 2004, Benson posed for the cover and a spread in FHM magazine and was named "baseball's hottest wife." In an interview with Howard Stern later that year, she vowed that if her husband ever cheated on her she would take revenge by sleeping with the entire Mets organization. Benson later explained the comment as "stupid humor to be understood by these idiots who take everything so literally." In July 2005, she began playing at the 2005 World Series of Poker in Las Vegas. She was ejected for excessive cursing.
The New York Times, having previously noted Anna Benson's "calculated outrageousness," wrote that "in her one year in New York, Anna Benson drove the Mets to distraction." Sports reporter Murray Chass, described by baseball's Hall of Fame as "a pioneer in the coverage of business and labor issues within baseball,"wrote of the Mets-Orioles trade, "Kris Benson doesn't have a good enough arm for the Mets to overlook his wife's mouth. ... And by trading Anna Benson, the Mets may have achieved what [former Yankees manager] Casey Stengel called addition by subtraction." Kris Benson himself later said that he felt New York traded him to Baltimore because of his wife,but Omar Minaya, general manager of the Mets, ultimately discounted speculation that her behavior had played a role, saying, "We just made a baseball trade." Mirroring Chass' linkage of the Bensons, Sports Illustrated opined that Anna Benson's "outlandish antics" had ultimately come to overshadow her husband's "few good years" in the major leagues.
Benson has worked with charitable organizations over the years such as the Pittsburgh Children's Hospital, Salvation Army and American Red Cross.The couple has a non-profit charity called Benson's Battalion that helped area police forces in the cities where her husband played.