MOSCOW—He's probably best known as the former president of Georgia. Or more recently, as a one-term academic at Tufts University, or to residents of Brooklyn, as the man about Williamsburg in fluorescent shoes.

Mikheil Saakashvili, the pro-Western ex-president of the small former Soviet country brazen enough to start a war with Russia in 2008, has tried to reinvent himself in unusual ways for a former head of state since leaving Georgia to live in self-imposed exile. But his latest reincarnation is particularly uncommon: On Saturday, Saakashvili took office in a second country trying to resist Russian advances.

Ukrainian President Petro Poroshenko appointed Saakashvili the governor of the Odessa region, Ukraine’s largest geographic area and sixth most populated region. It’s also home to Ukraine’s largest seaport, sitting between the recently-annexed territory of Crimea and the strategic, Russian-supported breakaway region of Trandnistria, in Moldova.

Saakashvili has been serving as an adviser to Poroshenko since February, and is not the first non-Ukrainian to be appointed to a prominent government position since the current president was elected. He brings considerable experience in the area of anti-corruption crusading and economic development – two areas where Ukraine is desperate to make improvments. And it doesn’t hurt that he has powerful American friends and can speak Ukrainian.

But as a politician with a polarizing history, Saakashvili also brings a legacy of baggage from his former positions that could affect Ukraine’s affairs.

As president of Georgia, Saakashvili was credited with instituting effective reforms in its notoriously corrupt police force and judiciary – which Ukrainian anti-corruption activists frequently talk about  emulating. But Saakashvili is also currently wanted in Georgia on embezzlement charges, which he argues are politically motivated.

Saakashvili has also been celebrated as an antagonist for Western-style democracy – but one of the main complaints against his presidency is that he pushed through reforms without allowing enough public participation.

The greatest political risk in importing Saakashvili to join the Ukrainian president’s governing team, however, may be in his special brand of antipathy toward Russia.

There is no love lost between Saakashvili and Russian President Vladimir Putin, who threatened during the 2008 war to “hang Saakashvili by the balls.” Saakashvili, for his part, has described Putin as someone who “likes to lie.

Putin’s government is fiercely derisive  of the type of pro-democracy social uprisings, known as “color revolutions” that spread to the former Soviet republics like Georgia’s 2003 Rose Revolution – and eventually brought Saakashvili to the top spot in his home country.

Thus far, the Kremlin is apparently laughing at Saakashvili’s appointment.

“Saakashvili is head of the Odessa region. The circus goes on,” Russian Prime Minister Dmitry Medvedev wrote in Russian on Twitter, adding in Ukrainian: “Poor Ukraine.”

But if Saakashvili’s star ascends in Ukrainian politics, relations between the old rivals may once again be no laughing matter.  Along with his new governorship, Poroshenko also gave Saakashvili official citizenship in Ukraine.