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 »

More articles by Gary Leff »

Can Southwest Airlines Handle Paid Seats, Bag Fees, And Boarding Changes—All At Once—Without A Total Operational Meltdown?

by Gary Leff

Mar 20 2025

Are all of the changes Southwest Airlines is making too much, too fast? Not for the passengers who have been largely negative on this like checked bag fees and basic economy restrictions, one thing after another taken away from customers with nothing really added that makes life better.

Here what I’m troubled by is whether they’ve taken on too many projects to quickly in order to actually pull them off without significant service disruptions and customer inconvenience.

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Southwest Flyers Feel Betrayed—And American Airlines Quietly Makes Its Biggest Status Match Offer Ever

by Gary Leff

Mar 20 2025

Everyone is mad mad at Southwest Airlines for abandoning its business model, customer focus, and core principles. They’re laying off employees, outsourcing, eliminating free checked bags, moving to (paid) assigned seats and devaluing Rapid Rewards.

So now is the perfect time for another airline to go after their customers aggressively, court them, and win them over. American Airlines is doing that – but just isn’t really telling anyone about it?

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Southwest Airlines To Overhaul Boarding—Lining Up Early Ends, 9 Boarding Groups Confirmed

by Gary Leff

Mar 19 2025

When Southwest Airlines moves to assigned seating they will no longer line everyone up prior to boarding. Like the rest of the airline’s moves, Southwest’s boarding process will converge towards being much more like other airlines.

Gone will be the stanchions, and having passengers line up by group and number. In its place with be 9 boarding groups.

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