Mike Fratello, color commentator for the Brooklyn Nets on YES, is known as the Czar of the Telestrator, which just goes to show anyone can be a Czar of anything. What the shit is going on here?
The Nets played the Raptors Monday, the 27th (and lost, brutally, on a Deron Williams turnover in the final seconds) so we can safely assume Mike is merely circling the date. But the other three are a mess. He does actually go on to explain what the hell he is getting at with each (hint: they are related to the teams/cities on the calendar!) but by the time he's done in Philly it seems like he's more final-moments Rasputin than Czar.
For your benefit, we've created a secondary GIF, with the answers provided.