Mikhail Fridman and Petr Aven epitomized the Russian oligarchs who used their fortunes to integrate into the global economy and shake off association with Russian President Vladimir Putin’s regime. Now the wheel of fortune is turning full circle.

Fridman has fled to Moscow from London via Israel, bitterly unhappy with life as a sanctioned businessman in Britain since Putin ordered Russia’s invasion of Ukraine. Aven may also have to weigh a return to Russia from Latvia, where authorities are threatening to revoke his passport.

Russia’s invasion of Ukraine changed everything for them and other billionaires who prospered under Putin until the U.S. and Europe imposed sweeping sanctions aimed at isolating the Kremlin leader and bringing his economy to its knees. The penalties largely failed to achieve those goals so far, though they destroyed the standing of many wealthy Russians abroad who remained silent or avoided direct criticism of Putin over the war.