Remember the last time D.C. Mayor Vincent Gray made a bet involving a sporting contest and a flag outside the Wilson Building? It didn’t work out so well.

“I look forward to the citizens of the City of St. Louis getting a lesson not only on the baseball diamond when the Nats take the series, but also in the uniquely unjust situation in which the District’s 618,000-plus residents find ourselves — denied voting representation in Congress and ultimate authority over our own budget and affairs — when our flag flies over Market Street in downtown St. Louis!” Gray said in a release, prior to Nats-Cardinals.

Well, the Nats lost. And the St. Louis flag flew.

And now it’s playoff season again, and the mayor is making the exact same bet, this time with Seattle honcho Mike McGinn.

“We’re ready,” Gray told Fox 5 Thursday morning, via WTOP. “We’re loaded for bear on this end. They haven’t won a road playoff game in 29 years. It was 1983, the last game they won. We want to make it 30 years consecutively.”

As silly as these bets are, Gray actually has a legitimate reason for choosing the stakes that he does.

“From my perspective, it’s a way of us being able to once again communicate that this is a city that’s taxed without representation,” the mayor later explained. “So if we are fortunate enough to be able to win, the flag that Seattle will fly will say No Taxation Without Representation.”

“It’s nice to be able to stand up for D.C. citizens and help them with a political cause,” McGinn said, which was sweet. “But I’ll tell you something, it’s gonna be awfully nice to see that Seattle flag flying in D.C.”

“Keep hope alive,” Gray countered.

(St. Louis flag image via NBC Washington.)