On January 7, 2010, multiple media outlets reported that beginning March 1, 2010, Jay Leno will move from his 10pm weeknight time slot to 11:35pm, due to a combination of pressure from affiliates and both Leno's and O'Brien's poor ratings.[10][11] Leno's show would be shortened from an hour to 30 minutes. All NBC late night programming will be preempted by the 2010 Winter Olympics between February 15 and February 26; a final decision about the programming changes was made by NBC on January 10.[12][13] O'Brien's contract stipulates that NBC can move the show back to 12:05 a.m. without penalty (a clause put in primarily to accommodate sports preemptions), leaving him with no apparent recourse other than resignation.[14]

On January 10, NBC confirmed they will be moving Jay Leno out of primetime on February 12 and intend to move him to late-night as soon as possible.[15] TMZ reported that O'Brien was given no advance notice of the change, and that NBC has offered him two choices: the hour-long 12:05am time slot, or the option to leave the network.[16] On January 12, O'Brien issued a press release that stated he will not continue on with the NBC program if it moves to a 12:05am time slot,[17] saying, "I believe that delaying The Tonight Show into the next day to accommodate another comedy program will seriously damage what I consider to be the greatest franchise in the history of broadcasting. The Tonight Show at 12:05 simply isn’t the Tonight Show." O'Brien has yet to seriously comment on-air about the changes, and has so far only made jokes about the possible changes during his monologues.

On January 21, it was announced that NBC had struck a deal with O'Brien. It was decided that O'Brien would leave The Tonight Show. The deal was made that O'Brien would receive a $32 million payout and that his staff would receive $12 million in the departure. O'Brien's last episode is expected to be Friday, January 22.