After stopping by-the-seat flights using seaplanes in between Boston, New York and Washington DC, Tailwind Air had pivoted to ad hoc charter.
After moving away from the by-the-seat private jet market using seaplanes, Tailwind Air has filed for bankruptcy.
There were two separate filings in the Eastern District of Virginia, Alexandria Division.
The filings were made Jan. 15, 2026.
Unlike the Chapter 7 filings last year from Jet It and Verijet, both Tailwind Air filings were under Chapter 11.
Chapter 11 provides for potential reorganization and continuation of business.
Chapter 7 provides for liquidation.
The filings were under Tailwind Air Services, LLC and Tailwind Air, LLC.
Each had a different list of creditors.
The Tailwind Air Services, LLC filing listed $5,968,297 in claims.
It included a $500,000 lien by the U.S. Small Business Administration and a $455,946 lien by Jim Hunt of McLean, Virginia.
Creditors included $30,775 due to Fly Alliance, a large charter operator that also manages aircraft and sells jet cards.
American Express was over over $280,000.
The IRS is owed $64,437.
Gogo Business Aviation is due $38,439, while Inline Aviation Group is owed. $213,125
Owl Creek Investments, listed as a trade account, is currently out $791,000, per the filing.
The Tailwind Air, LLC filing listed liabilities of $1,372,528.
Creditors included Flightsafety due $198,405, Dassault Falcon Jet for $184,449, and FBO chain Atlantic Aviation for $74,465.
Tailwind owed Billy Bey Marina in Weehawken, New Jersey in $81,400.
Blade Urban Mobility is due $16,731.
Harbor Fuels of Boston is out $98,242, while Everest Fuel owes $55,249.
The filing lists over $75,000 in unpaid wages.
Both filings indicated assets of less than $50,000.
In 2021, Tailwind Air launched seaplane flights connecting New York City and Boston.
At the time, CEO Alan Ram said, “Our service combines the accessibility of the train with the speed of a flight.”
Ram told the media, “By cutting travel times 40 percent to 60 percent, Tailwind Air’s premium service reduces aggravation and opens up half-day business trips.”
The eight-passenger seaplanes enabled customers to arrive 10 minutes before departure.
By 2022, the service had expanded.
In October 2022, Metropolitan Airport News reported:
‘With the addition of Washington, D.C., Tailwind Air now serves nine destinations from its Manhattan base. Manhattan destinations are Boston Harbor – Fan Pier Marina (BNH), Washington, D.C, East Hampton, Sag Harbor, Shelter Island, Montauk, Provincetown, Plymouth, and Bridgeport. For commuters, Tailwind Air offers heavily discounted prepaid books of 10, 20, and 50 tickets, which can be shared with colleagues, friends, and family.’
According to Ram’s LinkedIn profile had $17 million in revenues in 2022.
Simple Flying and CH-Aviation reported that the scheduled by-the-seat flights were stopped in late 2024.
Before starting Tailwind Air, Ram was a strategy director at Northrop Grumann.
Tailwind Air continued to operate on-demand charter flights.
At the time, its charter fleet reportedly included a Dassault Falcon 50, Falcon 900, Cessna Citation CJ3, Pilatus PC-12, and Beechcraft King Air 250.
Ram did not immediately respond to a request for comments.
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