United CEO Scott Kirby Roasted Over 2011 Halloween Show in Drag

by Gary Leff

The internet is gong crazy to discover United Airlines CEO Scott Kirby in drag, trying to link it to his efforts at pilot recruitment from diverse communities. Traditionally commercial airline pilots are older white men, and in the face of a shortage of pilots the airline has gone out of its way to find more pilots among people that don’t usually make the years-long expensive investment for their career.

Context: this is the US Airways Halloween party from 2011. There was a musical costume tradition under then-CEO Doug Parker (Halloween is his birthday).

There’s no real link between expanding the pool of potential pilots, and Scott Kirby doing Halloween dress-up at US Airways and later American Airlines. And there’s no impact to safety. The truth is for virtually all flights and all passengers it doesn’t matter who your pilot is.

But these videos were fun. Kirby, by the way, also performed as Kesha in 2014:

And this is the airline’s top executives doing Gangham Style.

The Halloween tradition was suspended at American Airlines during the pandemic. Kirby is at United now (and has been since 2016). These performances just aren’t American CEO Robert Isom’s style. The last great Halloween affair was in 2019 where Doug Parker performed as Billy Ray Cyrus.

In 2018 Parker played Boy George, lip syncing Karma Chameleon with a giant chameleon running around in the background. He ended that effort declaring “that’s how you make culture a competitive advantage!” In the 2019 performance Parker merely ends with “how great was that? Just kidding I know it wasn’t very good. We tried.”

Scott Kirby’s United does tend to lean left politically, as many corporations do. I’m old enough to remember when Big Business was the bogeyman of the left. Now they’re often allies, and anathema to conservatives. United supported bringing back affirmative action in California and imposed employee vaccine mandates before the Biden administration did. They encourage use of pronouns in emails and use them on name tags.

I’m just not sure there’s a ‘conservative airline’ alternative, if you want to choose your carrier based on ideology. Nor is there a conservative major hotel chain. Nonetheless, the video of Scott Kirby from 2011, dressing up and performing for employees at Halloween, was meant to humanize and bring executives down a peg and to entertain and really has nothing to do with today’s controversies.

Update: I’d add that if you’re going to make an issue out of Scott Kirby’s Halloween performances from a decade ago, then you sort of need to grapple with this too I think?

About Gary Leff

Gary Leff is one of the foremost experts in the field of miles, points, and frequent business travel - a topic he has covered since 2002. Co-founder of frequent flyer community InsideFlyer.com, emcee of the Freddie Awards, and named one of the "World's Top Travel Experts" by Conde' Nast Traveler (2010-Present) Gary has been a guest on most major news media, profiled in several top print publications, and published broadly on the topic of consumer loyalty. More About Gary »

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  1. I’m just thinking – what would be a good drag queen name for Kirby? Thoughts anyone?
    Here’s mine – how about:

    Miss DeConnection

    or

    Penny Pincher

  5. As a 1K of the “G” persuasion, it gives me enormous amounts of joy to know that my CEO is FIERCE! Do the MAGA Trash know that Kirby is a father of five, or are they assuming that he’s a Drag Mother of five? We now absolutely have to have a Lip Sync For Your Life between Kirby, Isom, and Bastian (for charity, of course).

  6. Kirby is a creepy looking guy. This stuff is creepy. Your attempt to cast it as normal and not a big deal contradicts the fact that 99.999% of CEOs would not even consider doing under any circumstances, didn’t ever, and you fully know that. Hiring people for their race not their ability to fly airplanes is racism, not the gobbledegook excuse you gave. You should remind yourself what that word means so you don’t excuse it in the future.

  7. DEI needs to DIE.
    This is revolting. Unfunny. Tells the world that critics personnel aren’t hired for ability, rather their identity politics.
    Mentally ill narcissist disconnected from the reality of customer expectations from the leader of a major corporation.

  9. I continue to be surprised that anyone would have a strong opinion of someone else wearing a costume.

  10. Suffice it to say that Parker was an incompetent manager, leading AA to be the uninspired and unprofitable airline it is today. Maybe fewer costume parties might have been in order?

  11. Kirby & Parker only did this because Herb and gang at that “other airline in Dallas” would do this *all* the time. Herb made an AWEFUL woman, with chest hair showing and all, but they did it for fun.

    the libtard Instagram/FB/Tik Tokers aren’t all MAGA, btw. they just don’t like some of the stupidity coming from the left, but this one is quite ill-informed.

    MAGA conservatives should also NOT listen to ANY Howard Stern shows before 2015, for what its worth. Trump was a regular guest and was totally awesome on the show. Not befitting of a President. though.

  13. It is a good thing that God is merciful and kind, however, he is being provoked by this dude and much more so by other perverts. Hey Kirby, God would much rather be kind. Tell him you’re sorry and stop you’re foolishness

  14. @Ohare is my second home
    your hate fueled comment cancels out anything you had to say that was actually valid. People like you are the reason why I’m a proud gay MAGAT. Maybe next time keep your simple minded commentary to yourself.

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