They've all, to varying degrees, recently had their feet in both the establishment and the opposition camps.
Until recently, Gudkov, a KGB veteran, was a Kremlin-loyal Duma deputy. He's now one of the regime's most outspoken critics.
Navalny is known for his fiery speeches at opposition rallies and his exposes of official corruption. But this week, he accepted a seat on the board of directors of the state-controlled airline Aeroflot.
Kudrin, a personal friend of Vladimir Putin, long served as finance minister. But since resigning last autumn, he's been scathing in his assessment of Kremlin policy.
And Prokhorov, who made and kept his billions by being loyal to Putin's Kremlin, is now flirting with the opposition and has formed his own political party.
When Russia enters times of political change, and its future direction is in doubt, much of the elite, and even some of the opposition, is forced to become political entrepreneurs -- hedging their bets in an effort to stay ahead of the curve of whatever new order eventually emerges.
But being a political entrepreneur also carries risks and costs.
In this week's edition of the Power Vertical podcast, I discussed the implications of this "politcal entrepreneurship" with special guest host Mark Galeotti, a longtime Russia-watcher and professor of global affairs at New York University.
Also on the podcast, Mark and I discussed the state of the "reset" between Moscow and Washington amid rising Russian-American tensions.
Listen to or download the podcast above, or subscribe to The Power Vertical Podcast on iTunes.