For four years Pickering represented District 42, based in Jones County, in the Mississippi State Senate, to which he was elected in 2003, after incumbent state senator Vincent Scoper decided to retire.[3][4][5]
Mississippi State Auditor
Pickering was elected Mississippi State Auditor in 2007, when he defeated Democrat Mike Sumrall, 55 to 45 percent, in the general election; he served in the position for over a decade.[6] He was sworn in on January 10, 2008, and succeeded Phil Bryant.[2][7] In 2011, Pickering received only third-party opposition as he defeated Reform Party nominee Ashley Norwood, 76 to 24 percent.[8]
In 2016, Pickering began an audit that found that only $3 million had been spent by GreenTech Automotive on automotive assembly equipment and parts in Mississippi, whereas it had promised to invest $60 million and create 350 jobs in Tunica County.[9] While the company had promised to create 350 full-time jobs, he found that it never created more than 94 full-time jobs in Mississippi at any time.[9][10] In July 2017, Pickering demanded that GreenTech and its CEO Charlie Wang pay Mississippi $6 million, because Greentech had not lived up to its promises.[10][11] He said: "I would venture that there isn’t really much of an operation in Tunica at all. This appears to have been a game of smoke and mirrors, and a corporate entity that never had any intention to deliver on the promises it made."[11] GreenTech declared Chapter 11 bankruptcy in February 2018.[12][13]
Pickering resigned in 2018 to lead the Mississippi Veteran Affairs Board.[14][1]
Mississippi Veterans Affairs Board
Pickering served as executive director of the Mississippi Veterans Affairs Board (MSVA) from 2018, when he replaced Randy Reeves, to 2022.[2] In May 2022, MSVA issued a press release stating that Pickering and his chief of staff were both resigning.[14] Following the press release, WLBT News reported that Pickering resigned because he had an unprofessional relationship with his chief of staff.[15][16] WLBT also alleged abuse of state time and alluded to a possible criminal probe.[15][16] Subsequent analysis raised what a journalist called "significant questions about how the agency operated under Pickering, a former state auditor and legislator, and the workplace culture he cultivated."[17]
In June 2012, Pickering was honored with the National State Auditor's Association's "National Excellence in Accountability Award" for his work on accountability and oversight regarding the American Recovery and Reinvestment Act of 2009.[22] In 2014, Pickering received the David M. Walker Excellence in Government Performance and Accountability Award, a national award presented once every two years to three auditors from the public sector accountability community who represent federal, state, and local governments.[23]