Behind the scenes: Inside Southwest’s 50th-anniversary celebration

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Fifty and one.

That was the overarching theme of Southwest’s party on Friday, although the official messaging certainly didn’t mention that.

Fifty years since Southwest used a loophole in then-heavily regulated airline industry to launch a low-cost carrier in wholly within Texas — something that arguably help it make one of the biggest contributions of any U.S. carrier toward lower fares and the related the democratization of air travel that’s come since.

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One year since a novel coronavirus led the globe to shut down, creating the gravest existential threat in the history of the airline industry — a sector grimly familiar with existential threats.

Southwest surely had been planning its 50th birthday for years, dreaming up ways to celebrate its employees, its passengers, its planes, and the cheeky “love” motif that still informs the airline’s stock ticker symbol.

(Photo by David Slotnick/The Points Guy)

And then the pandemic happened. Like every other airline in the United States and across the world, Southwest saw demand drop to unimaginable levels — worse than what happened in the aftermath of 9/11 or the 2008 financial crash. Plans changed.

Then the vaccine came and distribution picked up, and the U.S. was able to largely reopen — safely. Over three months, travel boomed, pent up demand surged with a vengeance, and the national mood changed. A celebration was back on the table.

Was the event Southwest threw on Friday the same as what it would have had SARS-CoV-2 never made its way around the world? Maybe. Probably not. It’s hard to tell, and Southwest’s event planners and PR staff were not inclined to discuss their best-laid plans.

What happened instead, only barely overshadowed by the operational challenges earlier this week when a third-party computer system failed, was a celebration of a half-century of risk-taking, of accessibility, of travel and, in line with the official messaging, of freedom.

(Photo by David Slotnick/The Points Guy)

TPG was exclusively invited to attend the celebration on Friday. In addition to interviews with leading airline executives — stay tuned for those — we were able to attend the employee event, which included a recounting of the last 50 years, a celebration of what is to come in the next 50, employee gifts, the unveiling of a special, sort-of related livery and more. Here’s what happened at the event.

A Live and Live-Streamed Party

In normal times, Southwest holds annual employee rallies at bases and stations around the country. Local employees get lucky and can attend without too much effort, and others — the gung-ho Southwest crew — will use vacation time and employee flight benefits to attend the party.

For obvious reasons, Southwest skipped the rally in 2020.

This year, the rally was back and bigger than ever, timed to 50 years to the day from when Southwest Airlines made its first commercial flight.

Held in a relatively new maintenance hangar at Houston Hobby Airport, the event was open to employees who won a lottery to attend.

It was a 90-minute program (which ran a few minutes over) featuring presentations from executives, photos and videos pulled from Southwest’s extensive archives (the uniforms of the 1970s were famously wild), jokes, giveaways, previews of future projects and innovations, and panels with employees who’ve been with the airline for the full half-century.

(Photo by David Slotnick/The Points Guy)

“I don’t know, I probably could count them on one hand,” one of the airline’s first employees said in a video panel with CEO Gary Kelly, answering the question “how many people were on your first flight?”

Emceed by Whitney Eichinger, Southwest’s managing director of culture and engagement, and Markus Lloyd, a public speaker who has co-hosted a handful past employee rallies, it was a fun event with a handful of surprises.

(Photo by David Slotnick/The Points Guy)

For one, there was the 50,000 Rapid Rewards points that Southwest announced it would gift to every employee. Sure, non-rev travel benefits are great, but that perk usually requires flying standby and hoping for an open seat. With the points, employees can book confirmed travel, with no need to wait until the last minute.

A few employees also won flight discounts, hidden in the swag bags every attendee got, along with the branded mask, hand sanitizer, lanyard and drink koozie.

(Photo by David Slotnick/The Points Guy)

Then there was the special livery, which brought the crowd to its feet for a standing ovation and photos. An airplane wrapped in an American flag (aside from the tail, which retained Southwest’s signature yellow, red and blue), the “Freedom One” plane was meant as a tribute to the nearly 8,000 of Southwest’s 56,000 employees who serve or have served in the armed forces.

(Photo by David Slotnick/The Points Guy)

As a link to the airline’s birthday: the theme of freedom. Honoring the employees and others who have fought for Americans’ freedom, and, with 50 stars for the 50 states, paying tribute to 50 years of the “freedom of travel” that came about as air travel was made relatively affordable for most.

(Photo by David Slotnick/The Points Guy)

The link may have been a bit tenuous. But judging by the standing ovation — the only other of which was given when CEO Gary Kelly took the stage — the link was solid enough and hit the right note, based on the reaction from the ramp workers taking photos of the plane and conversations with employees at the event.

Southwest has certainly had its share of labor disputes — like any airline — but this was clearly a day for celebration.

(Photo by David Slotnick/The Points Guy)

As the event wrapped, attendees headed outside into the Houston heat, where they could celebrate and party with food trucks, temporary bars, and a concert with the backdrop of the Herbert D. Kelleher commemorative plane, a Boeing 737-700 painted in Southwest’s original colors.

An emotional and exclusive flight

Southwest took to the skies for the first time on June 18, 1971, flying one of its four Boeing 737-200 jets from Dallas Love Field (DAL) to Houston Intercontinental Airport (IAH), and then on to San Antonio (SAT).

On Friday, it flew the first leg of that trip in tribute, but in reverse. And from a different airport.

Hey, a lot can change in 50 years. Although Southwest again flies to Intercontinential, now known as George Bush Intercontinental Airport, the airline operates into both Houston airports and maintains a major operating base at Houston Hobby (HOU).

(Photo by David Slotnick/The Points Guy)

After unveiling the Freedom One plane at Houston Hobby and breaking a few ceremonial bottles of champagne, the airline pushed the plane out of the hangar to prepare it for the first passenger flight in its new paint.

(Photo by David Slotnick/The Points Guy)

The jet was to fly just under 45 minutes to Dallas Love Field, Southwest’s headquarters, where the 50th birthday celebration would be extended to a few lucky passengers who happened to be passing through that day.

(Photo by David Slotnick/The Points Guy)

Southwest’s 737-800 seats up to 175 passengers. This charter flight had about 50. Among them were CEO Kelly, President Tom Nealon, board members, PR and marketing staffers, the livery’s designer and a small gaggle of in-house photographers — and a crew made up entirely of Southwest employees who have served in the military.

There was a brief wait on a taxiway — an air traffic control delay at Dallas, our pilot said. “If you know anyone at air traffic control, give them a call and ask them to get us in,” he joked. “Actually don’t, your phones should be in airplane mode by now.”

The delay was short, and we were airborne quickly.

It was a charter flight, not a normal commercial one, so not all of the normal rules applied.

(Photo by David Slotnick/The Points Guy)

Plenty still did, however, including safety presentations and prohibitions against passengers bringing their own alcohol on board and drinking it.

But this was a special occasion, and airline leadership wanted to mark it with a toast. The flight attendants passed out the champagne, and Kelly walked to the front of the cabin, where another flight attendant helped him activate the public address system.

(Notably, Southwest is not currently offering alcohol on its commercial flights due to an increase in unruly passengers).

“It is an absolute miracle that we are here today celebrating the way that we are,” Kelly said. “More than any other year, it really just hit home to me how important our people are. And so I just want to toast, not just to you all, not just to the folks who’ve been here in the past, but it’s all about the future.”

(Photo by David Slotnick/The Points Guy)

“We’re going forward,” he added. “And so let’s get the right people, let’s hang on to them, let’s empower them, and let’s get them to fly us to the next level. I love you guys, here’s to you,” Kelly said, before toasting and sipping.

A flight attendant, the one who had passed out the champagne, came on the PA system with a heartfelt recollection of her time in the military, training recruits who were heading to Iraq.

“I’d sing this at the end of training, and it applies today,” she said, before performing an emotional rendition of “I Believe I Can Fly.”

Just a few minutes later, we dipped below 15,000 feet on our descent, and the captain came on to remind us that yes, we had to follow the standard safety rules, meaning it was time to take our seats and fasten our seatbelts.

The flight was supposed to approach DAL by way of a new navigational point, named “HERBZ” by the FAA, in honor of Southwest founder Herb Kelleher. But for reasons that were not quite clear, the flight did not take that exact approach. But the nav point, just a few miles away, lives on as a tribute to the man who helped found and helm Southwest through its revolutionary early days.

(Photo by David Slotnick/The Points Guy)

After the jet bridge was extended and the aircraft door was open, Kelly and a few others departed for the office, while the rest of the passengers had a few minutes to don high-vis vests and head down to the ramp, where we had a chance to see the plane again, take photos, and explore.

(Photo by David Slotnick/The Points Guy)

But in classic Southwest fashion, the aircraft would not be idle for long; It was already entering revenue service, scheduled to depart for Tulsa, Okla. (TUL) just a few hours later — a bit longer than a typical Southwest turn, but still a fast launch back into normal service. The catering trucks were already pulling up to load the jet with provisions for its next leg.

Birthday Presents for Customers

It was a fun event for the employees in attendance — at least judging the audience reactions and the few I had a chance to chat with. But, as many presenters said throughout the day, the employees are only half of what makes the airline run. The other half: customers.

So it was only fitting for the celebration to be extended to them, or at least a lucky few who happened to be in the right place at the right time.

(Photo by David Slotnick/The Points Guy)

We walked over to baggage claim, where the airline had cordoned off a belt and loaded it up with prizes in the form of wrapped presents.

(Photo by David Slotnick/The Points Guy)

Everyone passing through — no matter where they were coming from or heading — was invited to head through the stanchions and claim a gift.

(Photo by David Slotnick/The Points Guy)

Passengers clearly had no idea what was going on, but were happy to participate. Announcements over the PA and signs around the baggage claim area helped explain it.

The gift boxes contained a variety of prizes, ranging from airline swag to a full, free vacation package. In the first few minutes, passengers left with beach towels, lunch boxes and more.

(Photo by David Slotnick/The Points Guy)

The event continued for more than an hour until all the gifts were gone.

Celebrating the past, moving toward the future

Throughout the event, even while celebrating the legacy Southwest has built, an eye was continuously cast toward the future.

The United States is continuing to emerge from the pandemic lockdown, with vaccination rates nearing herd immunity levels in some states and CDC guidelines implicitly endorsing a reopening.

Travel demand is booming, with domestic and regional leisure demand topping pre-pandemic levels, and business travel starting to return sooner than even the most bullish travel executives and analysts have predicted.

More: Thank You, Herb: 10 Reasons to Be Grateful for Kelleher’s Southwest Airlines

The road to recovery is not expected to be linear, however. A normal seasonal dip in leisure demand is expected this fall, with business travel likely not yet recovered enough to make up for the reduction in vacationers.

Still, the airline industry is in a better position than it could have hoped to be a year ago. For Southwest, which managed — by the skin of its teeth — to emerge from the crisis without layoffs or furloughs, it seems an appropriate time to reflect on the value of its employees over the last half-century — while looking forward to the next one.