(CNN) -- The careers of Russian oligarchs who have sought to wield power against the Kremlin in the media or politics have not tended to go far.
Mikhail B. Khodorkovsky, an oil magnate who backed an opposition party, has been in jail since 2003 and was convicted in 2005 on charges of tax evasion and fraud.
Vladimir A. Gusinsky and Boris A. Berezovsky, both of whom owned media outlets that were critical of the government, fled the country.
During the 1990s, it was common for oligarchs to oppose the Kremlin, said Henry Hale, director of the Institute for Europe, Russian and Eurasian Studies at George Washington University.
But once Vladimir Putin became president in 2000, "He started making examples of high-profile business people/oligarchs," Hale said.
Khodorkovsky, once Russia's richest man, was building an organization that could have served as a platform from which to challenge Putin in 2004, Hale said. "His real sin was mobilizing a campaign that seemed aimed at the presidency," he added. Khodorkovsky's jailing in 2004 "served as an example for most of the others," Hale said. "You didn't see many other big business people openly challenging the government since that time."
Instead, wealthy Russians have been careful not to draw the Kremlin's ire, he said. "They either laid low or supported the Kremlin's leadership actively."
Now, it's Mikhail Prokhorov, the owner of the New Jersey Nets whose $18 billion puts him among the world's richest people and who announced Monday he is running to replace Putin.
Though Prokhorov is unlikely to topple the incumbent, his fate could prove more benign than that of many of his fellow oligarchs, said Stephen Cohen, professor of Russian studies and history at New York University.
"He would not do it without the support of Putin or the men around Putin," said Cohen in a telephone interview. "He's not an independent actor ... his wealth is still dependent on Kremlin approval."
Prokhorov, like all the oligarchs who remain in Russia with their wealth intact, has made political and probably financial accommodations with the Kremlin, said Cohen, author of "Soviet Fate and Lost Alternatives."
Among Prokhorov's assets are vast mineral holdings that remain underground. "He'd like to sell them outright, or at least a controlling share of them, to Western countries so he can cash in while his political standing is OK," Cohen said.
But companies in the West will not deal with him or any other oligarch unless a commission established in Russia for such investment approves it, he said. "And the chairman of the commission is Putin."
That means Prokhorov is unlikely to do anything to offend Putin, Cohen said.
So, why is he running against him?
As things now stand, Putin will be running against Gennadi A. Zyuganov, the longtime leader of the Communist Party, which represents the only real electoral opposition in the country, according to Cohen.
Though not well-funded, the party is well-organized and efficient and could make Zyuganov a more formidable opponent at the polls by the March election, Cohen said. That scenario is even more likely if Zyuganov benefits from protest votes by the thousands of Russians who have taken to the streets in recent days, Cohen said.
If the demonstrators and their sympathizers are members of the affluent middle class, as some observers have suggested, "Then it would make sense to give them somebody other than the Communists to vote for -- if you're looking to divide the anti-Putin vote," he said. "They'll vote for the so-called successful businessman."
Prokhorov's candidacy would likely draw the anti-Putin vote away from the Communists and divide the opposition, Cohen said.
"They think they know what they're doing, and I guess they do," he added.
But Hale was not persuaded that Prokhorov's candidacy is fake. "Conspiracy theories sometimes, actually, are just conspiracy theories," he said in a telephone interview. "In this particular case, it seems to be real." Citing the civil unrest shaking Russia, he said, "people like him are sensing now's the time to criticize the Kremlin.
Still, Hale acknowledged, Prokhorov appears to have hedged his bets. "He has criticized people around Putin, but not Putin himself."
But even if pseudo-candidates wind up in the election, that's not necessarily a bad omen for democracy, Cohen said. More choice "is the foundation of a democratic system," he added.
One reason that suggests Prokhorov may be sincere in his putative effort to unseat Putin is the fact that his sister runs quasi-academic journals financed by her brother that are frequently critical of the Kremlin, said Harley Balzer, a professor of government at Georgetown University. But he, too, said it was not clear. "It's an important story; I wish we knew what the hell was going on," he said in a telephone interview.