After joining the Prince George's County Sheriff's Office, Jackson became the Fraternal Order of Police 112/DSA union president. In 2002, Jackson won the election for county sheriff by a narrow margin against the incumbent sheriff, Alonzo D. Black. Jackson was also the President of the Maryland Sheriff's Association until his retirement in 2010. Jackson is a member of the American Legion post 275; is a member of the Moose Lodge 453 and the Mitchellville Kiwanis Club. His 2010 campaign for County Executive of Prince George's County was unsuccessful when he lost to Rushern Baker. Jackson's department created the first 24-hour domestic-violence unit in the State of Maryland He is a recipient of the 2008 Victims' Rights Caucus Award, and the Allied Profession Award. In 2007, he also received the Maryland Network Against Domestic Violence, Law Enforcement Officer of the Year Award. His department also received the 2007 Governor's Award. Pursuant to Maryland Common Law, Jackson's position as the elected sheriff made him the senior law enforcement official of his jurisdiction and his authority superseded all others within the county. Jackson, a Democrat, served for two terms, from 2002 to 2010. The area that he served contains an estimated 820,852 residents, holds the Washington Redskins Stadium, the University of Maryland, College Park, and the National Harbor. Although violent crimes had dropped since 2006, in 2007, Prince George's County reported over 130 homicides, the highest rate of any county in Maryland.
Berwyn Heights mayor's residence drug raid
In July 2008, Jackson's agency, investigating a drug-smuggling ring, raided a private residence in Berwyn Heights, Maryland, handcuffing and interrogating those inside, and shooting two dogs. Almost immediately afterward, the home was revealed to be that of Cheye Calvo, the mayor of Berwyn Heights. The incident ignited much local and national controversy, with allegations of excessive force, civil rights violations, and failure to co-ordinate with the Berwyn Heights Police Department. Jackson spoke at a number of press conferences following the incident, in defense of his Department's role in the raid. Despite the controversy, the department did not officially clear the Calvos of wrongdoing until 2010. While an internal investigation by the Sheriff's department claimed to have found no wrongdoing, and Sheriff Jackson publicly praised the officers involved, a lawsuit was filed, and the Federal Bureau of Investigation is monitoring the situation, as part of a civil rights review requested by the Calvos. In addition, Maryland Senator Thomas V. "Mike" Miller said, "The people of Prince George's County demand better" and also stated that he pleaded with Jackson to make an adequate apology for the incident. It took more than a year for Sheriff Jackson to offer any kind of apology whatsoever. In August 2010 while campaigning to be elected county executive, Jackson stated, "We've apologized for the incident, but we will never apologize for taking drugs off our streets," adding "Quite frankly, we'd do it again. Tonight." Prince George's County settled the lawsuit in 2011, paying an undisclosed sum to Calvo, and agreeing to create new regulations on the treatment of animals and the deployment of SWAT teams.
Family dog killed while serving eviction notice
Two days after the Jackson said, "Quite frankly, we'd do it again. Tonight.", another family dog was killed by one of his deputies. The deputy was supposed to wait for animal control to arrive but failed to follow proper procedures for serving an eviction. As a result, another county resident, Donna Williams of Forest Heights was the latest victim of what Mayor Calvo said, "is part of a pattern." According to county spokeswoman Sergeant Yakeisha Hines, "the only reason Animal Control is asked to be on scene, is to take possession of the dog after the family is evicted." In this case, Sheriff Jackson's agency was not evicting Donna Williams, but only serving her with an eviction notice. Donna Williams indicated that she did not believe they knocked. When asked for comment, spokeswoman Hines merely stated, "That's her opinion." Williams was hospitalized for post-traumatic stress disorder. In addition, Williams said Jackson told her that he was sorry but that his deputies "did what they had to." Even before an internal investigation by the department was completed, Sheriff Jackson said he "did the right thing."
Campaign treasurer indicted for union embezzlement
Jackson testified in August 2010 that one year before his campaign treasurer was accused of embezzlement from the local Fraternal Order of Police lodge, he had rejected the union president's requests that he review evidence of the alleged embezzlement. After his treasurer was indicted, Jackson suspended her with pay from her Sheriff's department position. When asked whether it was permissible to steal union funds, Jackson stated, "I have no opinion on that."
Personal life
Jackson is married to Kim Jackson and has one child.