donate half of their winnings to charity. This was the first-ever man-versus-machine competition in the show's history. At the end of the first episode, in which only the first match's Jeopardy! round was aired, Rutter was tied with Watson at $5,000, while Jennings was in third with $2,000. After the second episode in which the first game was completed, Jennings remained at third with $4,800 while Rutter at second had $10,400. The competition ended with Watson with $77,147, Jennings with $24,000, and Rutter with $21,600. Below his response during the Final Jeopardy! round, Jennings wrote on his screen "I for one welcome our new computer overlords." It was the first time Rutter had been defeated against any human player, although the defeat is not on Rutter's Jeopardy! official record, as the competition was deemed an exhibition. Jennings wrote about playing against Watson for Slate. In 2014, Jeopardy! aired a special five-week Jeopardy! Battle of the Decades tournament. Jennings made it to the finals along with Brad Rutter and Roger Craig. Jennings placed second, winning a $100,000 prize, and Rutter won first place, securing a $1-million prize. In the 2019 Jeopardy! All-Star Games, with 18 former champions, Jennings was one of six captains, choosing 2015 Jeopardy! Tournament of Champions runner-up Matt Jackson and 2012 Jeopardy! College Champion Monica Thieu (who coincidentally eliminated Jennings in a 2016 episode of 500 Questions) to complete his three-person "Team Ken". Team Ken finished second to the team captained by Rutter, with Jennings winning $100,000, one-third of the $300,000 second-place prize. This brought his lifetime Jeopardy!-related winnings to $3,522,700. In June 2019, Jennings said a future face-off between him and Jeopardy! record-holder James Holzhauer would be "irresistible." A November 18, 2019 announcement by ABC named Jennings, Holzhauer, and Brad Rutter would return to Jeopardy! in a tournament to determine who is the "Greatest of All Time" scheduled to air on January 7, 2020. Jennings won the championship to be crowned with the "Greatest of All Time" title and a first-place prize of $1 million. Outside Jeopardy! Taking advantage of the notoriety of Jennings' losing Final Jeopardy! answer, H&R Block offered Jennings free tax planning and financial services for the rest of his life. H&R Block senior vice president David Byers estimated that Jennings owed about $1.04 million in taxes on his winnings. Also, BBDO created an advertisement for FedEx in the USA Today newspaper three days