Breaking Down Charles Barkley and Damian Lillard Vs. Skip Bayless

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Charles Barkley has publicly beefed with Skip Bayless for a number of years. It’s at least been the case since 2009, and it honestly wouldn’t astonish me if Barkley’s dislike of Bayless dates back to the 1990’s when Barkley played in the NBA and Bayless was doing what he does now in newspapers rather than on TV. Damian Lillard is now involved in this stuff, too, so let’s start working backwards.

On Tuesday night, Barkley was narrating a highlight of Damian Lillard draining a three on the Lakers and said, “I hope y’all heard me, America, Skip Bayless, take that with your punk ass”:

And then there’s Skip’s whole feud with Damian Lillard. Last week, Skip said he wasn’t buying ‘Dame Time’ and Lillard responded:

On Undisputed, Skip told his side of the story:

Skip says that in late May he ripped Lillard for saying he didn’t want to go to the bubble if the Blazers had no shot to get into playoffs. Skip said he was a very nice player, but not the face of the league caliber like LeBron James and that he’s never won anything. Lillard tracked down his number through Chris Haynes and Stephen A. Smith, and they had a phone conversation. Skip claims he not only didn’t backtrack on the criticism but doubled down on it:

Skip adds he brought up Lillard’s shooting stats in the fourth quarters and one overtime of last season’s conference finals against the Warriors (8-26 from field, 5-17 percent from deep, and -30) and told him he wasn’t clutch. This all would have made for a great podcast.

And now it’s pretty easy to see why Barkley is on team Dame here. This is all a variation of the argument about how important rings are to aggregate greatness. Barkley is constantly chided by Shaq on Inside the NBA about their championship disparity, as though it’s supposed to be a universal trump card in winning an unrelated argument.

As of late, Barkley has been repeatedly predicting that Lillard and Blazers would shock the no. 1-seeded Lakers, and trollingly brought out a broom Tuesday night after Portland won Game 1.

Forgive me for bringing up something that doesn’t have anything to do with his past postseason performance, but there are few things more electrifying in sports right now than watching Lillard pull up from 30-40 feet. Here’s a highlight reel from this season:

According to a very interesting statistical analysis in the Wall Street Journal, Lillard shot 42.6 percent from that range this season. You could’ve told me it was 55 percent and I wouldn’t have immediately called BS. They are like layups for him and he keeps getting better at it. It’s truly wild to think about how a human who can do that would also get so agitated about TV opinionist criticism.


Written by Ryan Glasspiegel

Ryan Glasspiegel grew up in Connecticut, graduated from University of Wisconsin-Madison, and lives in Chicago. Before OutKick, he wrote for Sports Illustrated and The Big Lead. He enjoys expensive bourbon and cheap beer.


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  1. Yikes Skip must be drinking the same blood that Rick Pitino drinks. The guy looks like the walking dead. About the only thing interesting I’ve heard from Skip recently was when Jalen Rose called him out for not playing HS basketball, even though Skip has claimed for all these years that he was a star outside shooter in High School. The only thing Skip was the star of was the nerd table in the lunchroom.

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