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Other than taking Crimea by force, what Putin done to outdo Obama.
Crimea was taken bloodlessly. A vast majority of the population support being part of Russia. Crimea has been Russian for many centuries until Soviet dictator Nikita Khrushchev gave it as a “gift” to the Ukraine in an internal (and at the time effectively meaningless) Soviet transfer.
As far as Puting outmaneuvering Obama on Ukraine, Obama supported the coup de’tat against the elected government because they were pro-Russian unlike the previous government which was pro-Western and pro-NATO. Obama hoped with the overthrow of the government it would bring Ukraine closer to the West. Putin, in response to Obama backing the coup, backed Ukrainian rebels opposed to the unelected government who assumed power after the coup. As a result of Russian backing, the rebels have created a de facto split in Ukraine between the pro-Western regions, which are under government control, and the pro-Russian regions, which are under rebel control in a stalemated frozen conflict that has effectively prevented Ukraine from becoming closer to NATO and the EU, something Russia would abhor.