On July 17 at Money in the Bank, Bryan won the SmackDown Money in the Bank ladder match which earned him a World Heavyweight Championship match at any point within the following year. On the July 22 episode of "SmackDown", Bryan declared he would cash in his Money in the Bank briefcase at the following year's WrestleMania. After several months of losing matches, Bryan began a feud with then World Heavyweight Champion Mark Henry on the November 4 episode of "SmackDown" after Henry challenged Bryan to a non-title match to prove that Bryan could not become champion. During the match, Big Show knocked out Henry, making Bryan lose by disqualification. As his friend, Big Show then urged a groggy Bryan to cash in his championship match, but Henry recovered and attacked both Bryan and Big Show before the match could start. Bryan suffered attacks from Henry the following two weeks. On the November 25 episode of "SmackDown", Henry was knocked out again by Big Show, at which point Bryan cashed in his briefcase for a title match and quickly pinned Henry, but SmackDown General Manager Theodore Long revealed that Henry was not medically cleared to compete and voided the match, so Henry remained champion and the briefcase was returned to Bryan. Bryan later admitted he betrayed his principles by not waiting for WrestleMania, but explained he felt strongly about exacting revenge on Henry and realized he may not make it to WrestleMania due to Henry's continued attacks. Regardless of his briefcase, Bryan won a fatal four-way match on the same episode of "SmackDown" to become the contender for Henry's championship. On the live November 29 episode of "SmackDown", Henry managed to pin Bryan to retain the title in a steel cage match. Also in November, Bryan started being involved in a romantic storyline with AJ.