Payton was designated for assignment by the Red Sox on July 7, , after being publicly disgruntled over his lack of playing time. On July 13, he was traded to the Oakland Athletics for pitcher Chad Bradford. On July 15, Payton hit a home run in his first at bat with the A's, and earned a cult status for a brief period after winning many games for the A's with an otherwise struggling offense. In 2006, Payton played regularly in the outfield for the Athletics while batting .296 with 10 home runs and 59 RBIs. On July 3, , he hit his 100th career home run. On December 8, Payton agreed to terms on a two-year, $9.75 million contract with the Baltimore Orioles. In March 2009, Payton suffered a shoulder injury while lifting weights.