On January 13, 2000, Bill Gates handed over the CEO position to Steve Ballmer, an old college friend of Gates and employee of the company since 1980, while creating a new position for himself as Chief Software Architect.
The Rock then defeated Big Show, on the March 13 episode of Raw Is War, to regain the right to face the WWF Champion, Triple H, at WrestleMania 2000 in a Fatal Four-way elimination match, also including Big Show and Mick Foley.
On May 21, at Judgment Day, The Rock faced Triple H in an Iron Man match with Shawn Michaels as the special guest referee. With the score tied at five falls each, and with seconds left on the time limit, The Rock was disqualified when The Undertaker attacked Triple H, thus giving Triple H the 6–5 win and the title.
The Rock won the WWF Championship for a fifth time at King of the Ring on June 25 by scoring the winning pin in a six-man tag team match, teaming with Kane and The Undertaker against Shane McMahon, Triple H and Vince McMahon, whom he pinned.
The Millennium Summit was held in 2000 to discuss the UN's role in the 21st century. The three-day meeting was the largest gathering of world leaders in history and culminated in the adoption by all member states of the Millennium Development Goals (MDGs), a commitment to achieve international development in areas such as poverty reduction, gender equality, and public health. Progress towards these goals, which were to be met by 2015, was ultimately uneven.
On the December 18 episode of Raw, The Rock won the WWF Tag Team Championship with The Undertaker, defeating Edge and Christian, before losing it back to them the next night at a SmackDown! taping
Near the end of 2000, investigators discovered illegal stock manipulation by Paul and corporate officer Stephan Gordon. Stan Lee Media filed for Chapter 11 bankruptcy protection in February 2001. Paul was extradited to the U.S. from Brazil and pleaded guilty to violating SEC Rule 10b-5 in connection with trading his stock in Stan Lee Media. Lee was never implicated in the scheme.