There are few playoff losses more tragic in Celtics history than Game 7 against the Miami Heat in Boston on Monday night. There are even fewer Celtics fans bigger than Bill Simmons.

The former ESPN writer and The Ringer mogul looked utterly distraught as he witnessed the Celtics on the wrong side of history against the Heat. Instead of becoming the first team to come back from down 0-3, they become the first team to force a Game 7 at home and still lose.

Simmons' face caught on camera perfectly captures the raw emotions of every Celtics fan in the building. A mixture of shock, sadness, and uncertainty over what comes next. His grief-stricken face soon made the rounds on NBA Twitter in hilarious fashion.

There's the viral tweet showing Bill Simmons as Succession's favorite sad boi, Kendall Roy. I'm sure as a huge fan of the show, Bill would appreciate the comparison.

There's also Bill Simmons compared to a 17th century painting called “Study Head of an Old Man”. Worth wondering how the man depicted in the portrait felt about the Celtic warriors of yesterday.

Celtics haters reveled in the sadness shared by two Boston media moguls in Bill Simmons and Dave Portnoy of Barstool Sports. The same anguish depicted in two very different ways.

Even the Heat Twitter account gave Simmons a courtesy wave after slaying his Celtics in Game 7.

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Bill Simmons himself reacted to his sad face going viral, agreeing that it depicted his emotions perfectly.

Sports pain is one of the most debilitating type of hurt out there. Witnessing it live and in that fashion probably amplified the pain for every Celtics fan in attendance.