Pickering was elected first auditor in 2007. He confirmed to Mississippi Today that Monday morning he would inform his senior employees that he was taking over the Veterans’ Affairs post. The position became vacant in late 2017, when former director Randy Reeves was appointed Under Secretary for Memorial Affairs at the U.S. Department of Veterans Affairs. Pickering explained to Mississippi Today that he had been discussing the matter for some time and had been praying about it. Pickering said that he felt it was the right fit, given his service in the National Guard. Gov. Phil Bryant would nominate a replacement for Pickering’s remaining term as auditor. This term runs through 2019. Bryant was the former governor who gave Bryant his big political break. After Steve Patterson, then-Auditor, resigned in a court settlement Kirk Fordice appointed Bryant as auditor. Bryant was serving his second term as a member of the state House of Representatives at the time. Pickering will be in charge of the state agency that assists service members to obtain federal and state benefits. According to the website of the state department Pickering will oversee the responsibility of helping service members secure federal and state benefits. Pickering previously served one term in the state Senate from 2004 to 2008. Pickering won the 2007 state election for auditor by 10 percentage points and has held the position since. The Clarion-Ledger reported in 2015 that Pickering was under FBI investigation for allegedly using campaign funds for his personal use. Pickering was also accused of using campaign funds for personal use, including a garage door at his home, a BMW car that he gave to his daughter, as well as an RV he claimed was for his own campaign. Pickering called these allegations a campaign stunt by his opponent, Madison Mayor Mary Hawkins Butler. Pickering was never charged.