Putin, it would seem, is flying high. He just won re-election again, easily. Russian military might and cyberwarfare expertise are feared again. He’s pulled Russia out of the Yeltsin vortex and made it great again.
But has he, really? He has taken Crimea, but Ukraine, which was this close to being under his control, is violently hostile. The likelihood of incorporating Ukraine into his political and economic sphere is very low at this point. Syria has been a victory so far, but now he has to find a political solution that works for him and everyone else. Russia has no real friends in the world, and is still suffering from economic sanctions. The economy is growing at a snail’s pace, particularly relative to China, and the country’s only real asset (oil) is becoming less valuable over time. He can’t get rid of corruption because it is the guiding principle of the political system. Finally, he has no clear heir, so no one knows what happens after he leaves.
Does that sound like winning to you? If your definition of winning revolves around the use of military power, maybe. Otherwise, no.