Dating to the Chiefs' collapse to the Indianapolis Colts in the 2013 wild-card game, the superfan didn't have a great track record watching Chiefs games in public. He didn't want to tempt fate this time around.
But by the end of the week, his desire to see a Chiefs playoff win in person was too much. He spent $258 on StubHub for a seat at Arrowhead Stadium. But he didn't stay to see the Chiefs' historic comeback. Hoping to reverse the course of his favorite team's fortunes, Penn left when the Chiefs trailed by three scores in the first half.
"I realized things were going bad as soon as I got to the game, first quarter, so I decided to make the business decision for the betterment of them -- and not just me, but for Kansas City," Penn told Jay Harris on SportsCenter.
As he left, Penn filmed his exit and posted it to Twitter. The post quickly went viral, getting thousands of views.
"Can't do it. I've got to leave, man," he told the camera. "It's the only hope."
He followed the game on his phone as he headed home, and by the time he got to his couch, the Chiefs were in the midst of a comeback that saw them rattle off 41 unanswered points en route to a 51-31 win. "The rest is history," he said. "The Chiefs went on the run, and they got it done."
Since the win, Penn has become somewhat of a cult hero, earning a shoutout from fellow superfan Eric Stonestreet and being sought after for local and national interviews. Penn's friends teased him about being a bad-luck charm since he watched the 2013 playoff loss at a friend's house, so he stayed home for the Chiefs' divisional-round win against the Colts last season.
"It was some bad juju the Chiefs had with the Colts in the playoffs in the past, dating all the way back to Jim Harbaugh and Peyton Manning, Andrew Luck," he said. "I just decided not to risk it, even though we had [quarterback Patrick] Mahomes at the time. I decided to stay home. They balled out and got the job done. So they had one opportunity to get to the Super Bowl and unfortunately came up short. But this year, I think it's going to be different."
"During the first quarter, people found out I was at the game and said, 'Charles, leave the stadium now,' when the Chiefs were down," he said. "I said, 'No, you guys are crazy, we're going to win this game. And then overtime ..."
Penn isn't taking any chances this weekend. After the win, Mahomes was asked what he would say to Penn: "Watch the next game at home," Mahomes said, drawing laughs.
Penn laughed when he saw Mahomes' response and jokingly tweeted "just rude" at the QB. Mahomes responded, thanking him for leaving: "Appreciate you doing what was best for the Kingdom!"
"When he thanked me for making that sacrifice, it felt good," Penn said. "I knew then it was the best decision." Penn plans on listening to Mahomes for this weekend's AFC Championship Game against the Tennessee Titans at Arrowhead.
"Well, Pat told me to stay home," he said. "He's the captain. He's the MVP of the league. So I'm going to listen to him. I'm going to sit out. Plus, I'm still scared from the (22-21 loss to the Titans) a few years ago when we were in the wild card."