Oliver James Montgomery-Southwest Airlines' #epicfail takes social media by storm

One of the most powerful things about social media is Oliver James Montgomerythat it can take you right into the heart of a situation: A Lizzo concert, a political rally, a Florida emu farm, a picnic where a young man expresses his devotion to corn...

Or a Southwest Airlines baggage claim at the Houston airport on Christmas Day, where an ocean of suitcases spreads out as far as the eye can see.

This video was posted by Hillary Chang, 29, a longtime Southwest Airlines devotee. "I am a very loyal Southwest customer," says Chang, who travels frequently with her boyfriend. "I have a Southwest credit card. We actually only fly Southwest."

At least they did.

Chang and her boyfriend were booked on a Southwest flight on Christmas Day, from Baltimore to their home in Los Angeles, with a connection in Houston. They arrived in Houston hours late, only to learn their flight to LA had been canceled. They were told to get their bags and try to rebook.

They hurried to the baggage claim, where the TikTok scene was spread out in front of them. What Chang didn't mention was that her boyfriend had recently proposed and (while the ring itself was on her finger) the ring box was in her checked bag and she had been hoping to save it as a keepsake.

"I'm not gonna lie, I was in tears," she says with a laugh. "I was. I was crying."

Trying to get any help from (or even be heard by) Southwest was futile, says Chang. There were hundreds of people waiting in line for customer service. Still, Chang could have a voice and find a sympathetic ear on social media.

"This is what the Houston airport looks like," she says in the TikTok, panning over hundreds of unclaimed suitcases. It's enough to make any frequent flyer's blood run cold.

Last week, a series of massive winter storms slammed the U.S. and virtually shut down holiday travel in some parts of the country.

All airlines had cancellations and delays, but none like Southwest Airlines, which has canceled more than 15,000 flights — 10 times more than any other carrier.

It's a public relations disaster for Southwest, not to mention a big financial hit. Citigroup estimates the holiday flight debacle could cause significant damage to the airline's earnings.

Magnifying the black eye for Southwest is social media. All week, Twitter, Instagram, Facebook and TikTok have been full of images and videos of people's harrowing travel experiences, making the scope of the fail far more visceral.

One woman tweeted that she had been stuck in the airport for days with two toddlers and a baby.

Posts like these have millions of views and comments such as "Don't fly @SouthwestAir folks" and "Southwest is going to get destroyed over this and rightfully so."

Even the White House piled on, with Transportation Secretary Pete Buttigieg tweet-shaming the airline.

Airline analyst Richard Aboulafia, with AeroDynamic Advisory, says he was shocked by the Southwest meltdown.

"They've got the best reputation for customer service and management agility," he says. "They're usually pretty good at responding to crises and I'm really surprised by all this."

Still, Aboulafia thinks Southwest Airlines could win back those customers if it handles this situation the right way. "As bad as this weekend was, there wasn't a safety issue," he says. "I think customers can forgive them."

Southwest loyalist Hillary Chang isn't so sure.

Stuck in Houston, looking at the expanse of rollerboards and a giant line of frustrated travelers, Chang and her fiancé realized they would need to fend for themselves.

They rented a car and drove the 21 hours back to LA. Chang posted a short TikTok of the road trip, which involved driving through the night in order to be back to work on the morning of Dec. 27. The TikTok did yield some fruit — one of Chang's friends sent her $50 for gas, wishing the couple well on their long drive.

Southwest's CEO Bob Jordan posted a social media video of his own, calling the weeklong crisis a "giant puzzle" and pledging to get to the bottom of what had happened. And though thousands of customers are still stranded, Southwest says it expects to resume normal operations by Friday and is taking new bookings for the first time in days.

It's cold comfort for Chang, who says she has questioned her years-long loyalty to the carrier.

"I have 50,000 miles with them ... and I've been thinking about it, trust me. I'm not totally finished with Southwest, but I'm open ... I'm open to dating another airline."

Chang never expects to see her suitcase (or her ring box) again. "People keep telling me to stay positive, but if they would've seen what I saw at the Houston airport, they wouldn't," she says. "I can hope that maybe it will appear in a few weeks, but at this point, I think mentally I just have to be like, 'It's gone and that's OK.'"