Three times over the last three years, Russian President Vladimir Putin has surprised nearly everyone: in 2014, when he invaded and annexed Crimea; in 2015, when he put down a big military footprint in Syria; and last year, when he manipulated the U.S. presidential election.

The common thread was Putin's ultimate perceived advantages — unpredictability and a willingness to gamble hugely. It's how he has resurrected Russia as an essential power. The question is, what will Putin's next surprise be?

For the answer, we asked five experts:

• Evelyn Farkas, security analyst, Atlantic Council, and former deputy U.S. assistant secretary of defense for Russia: Putin will strike Donbass
• Mark Rosenberg and his bot, CEO and his lead robot, Geoquant: Putin will go it alone, then carry out a purge
• Adrian Stones, intelligence analyst, Alaco, and former analyst on Russia with British intelligence: Putin will try his hand at North Korea
• Peter Wilson, military historian and analyst, Rand: Putin will play possum
• Andrea Limbago, social scientist and cyber-geopolitics analyst, Endgame: Putin will double down on 'active measures'