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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Wheelchair Requests Are Becoming An Airport Hack — On Some Long-Haul Flights, 30% Of Passengers Use Them To Board First

Jan 23 2026

Wheelchair assistance is increasingly being used as an airport “hack”: it can mean skipping long walks, cutting security lines, and boarding early—often with an entire family in tow. On some long-haul flights, as many as 30% of passengers now request wheelchairs, and the result is predictable: real disabled travelers get crowded out while “Jetbridge Jesus” miracles happen the moment boarding starts.

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Must-Pass Shutdown Funding Bill Sneaks In Airline Policy Changes — “Two Pilots Forever” And A DOT Review To Chill Joint Ventures

Jan 23 2026

A must-pass funding package to avoid a January 30 government shutdown is carrying quiet airline policy moves that will matter far more than the headlines about FAA dollars.

The major pilot union is celebrating “two fully rested pilots at all times,” but the language is really a spending restriction that prevents the FAA from studying new technologies that might improve safety, and separate language orders the Department of Transportation to revisit decades-old international aviation policy that has worked to open market access and foster competition.

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Who Really Issues the New Bilt Card? The Four-Company Stack Behind Bilt Card 2.0

Jan 23 2026

The new Bilt Card doesn’t work like a normal Chase or Amex product where one bank issues, services, funds, and owns the economics end-to-end. Bilt Card 2.0 is a split stack: Column is the bank and lender of record, Cardless runs servicing and the tech layer, Fidem (and its capital partners) fund receivables, and Bilt provides the rewards program—on Mastercard rails. Once you see the roles, the money flows (interchange, interest, and who gets paid for what) make a lot more sense.

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United Announced A Chicago “Line In The Sand” Meant To Prevent New Flights — American Just Added Routes Anyway

Jan 22 2026

United’s CEO Scott Kirby went out of his way on the earnings call to “draw a line in the sand” in Chicago—promising United will add flights to match any American expansion at O’Hare. The point of saying it publicly wasn’t bravado. It was deterrence: to signal to American (and to analysts) that new Chicago capacity will be met in kind, making growth less attractive for both airlines.

American’s response came fast anyway, announcing new routes from O’Hare—turning Kirby’s game-theory warning into an immediate test of whether this becomes a real fare war or a negotiation by headline.

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United Adding More Widebody Planes Than Any US Airline Since 1988 — Here Is Who Did More

Jan 22 2026

United made a big claim in its latest earnings update: in 2026 it expects to take delivery of roughly 20 Boeing 787s—more widebody aircraft in a single year than any U.S. carrier has taken since 1988. The “since 1988” reference isn’t random; it points to one standout widebody delivery spree that still hasn’t been surpassed.

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Delta Delay Cost Them Their Alaska Cruise — And A 19th-Century US Law Made It Impossible To Catch Up To The Ship

Jan 22 2026

A family’s Alaska cruise was effectively over before it began after a delayed Delta flight out of Detroit caused them to miss the only Minneapolis–Vancouver connection that could reach the ship on time.

Delta rebooked them to try to save the trip, but the replacement flight didn’t pan out, and once the cruise sailed there was no “meet it at the next stop” option, because a 19th-century U.S. maritime law prevents cruise ships from carrying passengers between U.S. ports.

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