On the July 7 episode of "Raw", Kane lost a number one contender's fatal four-way match to Batista (Batista would advance to the World Heavyweight Championship match at The Great American Bash), leading him to attack commentators Michael Cole and Jerry Lawler, thus turning heel in the process. At The Great American Bash, Kane interfered and attacked both the champion CM Punk and the challenger Batista, causing the match to end in a double disqualification. In September, Kane began a feud with Rey Mysterio that lasted through Survivor Series. On the March 2 episode of "Raw", Kane pinned Mike Knox in a triple threat match, also involving Rey Mysterio, to earn a spot in the Money in the Bank ladder match at WrestleMania 25, a match ultimately won by CM Punk. During the 2009 draft Kane beat The Brian Kendrick for a draft pick and, later in the night, was drafted to the SmackDown brand. There, Kane feuded with CM Punk and defeated him at Backlash. He then took a break to tour India and also heal injuries, returning at The Bash to assist Dolph Ziggler in his match with The Great Khali by hitting Khali with a steel chair, allowing Ziggler to win. This started a feud with Khali, whom he defeated at SummerSlam and in a Singapore Cane match at Breaking Point. Alongside Chris Jericho, Kane was co-captain for the victorious Team SmackDown at Bragging Rights. Kane then unsuccessfully challenged Jericho in a number one contender's match for an opportunity to face World Heavyweight Champion The Undertaker and Big Show in a triple threat match at Survivor Series. In November, Kane reunited with The Undertaker to feud with Big Show and Jericho, thus turning face. At WrestleMania XXVI, during the Money in the Bank ladder match, Kane was unsuccessful in claiming the briefcase as Jack Swagger won the match. Over the next few months, Kane was involved in sporadic singles matches on episodes of "SmackDown", including a loss to CM Punk in May in a qualifying match for the World Heavyweight Championship match for the Fatal 4-Way pay-per-view event.