Hillary Clinton knows Vladimir Putin more intimately than the rest of these losers.

When asked what her relationship with Putin was at the Democratic debate, Clinton did a dramatic, unexpectedly prolonged “it’s complicated” face. Perhaps she was trying to communicate that she’d had far more experience dealing with the Russian president than the senator and former governor who flanked her. And Putin has a long public track record of being a weird dude. But it was a strangely heavy pause before she answered.

“It’s interesting,” Clinton said, and then looked down and smiled, as if reliving a private memory too controversial to share with the class. “We’ve had some very tough dealings with one another,” she added.