Michael Dell flies to Madeira as Dell Technologies closes Pentagon deal

Michael Dell flew his Gulfstream G650ER, N228ZD, from Westchester County Airport to Cristiano Ronaldo International Airport in Madeira on June 20, a 5-hour 38-minute transatlantic hop that arrived in the early evening. The flight, tracked by Celebplanes, departed the New York area just a day after his aircraft completed a series of shorter hops along the Eastern Seaboard.

The trip lands in Madeira the same week Dell Technologies secured a $9.7 billion Pentagon contract to supply Microsoft software across the U.S. military, per a Euronews report on May 28. The five-year Core Enterprise Technology Agreement, awarded by the Department of War, comes weeks after President Donald Trump publicly endorsed the company at a White House event, and follows a $6.25 billion donation by Dell and his wife to Trump Accounts in December 2025.

Dell, who controls roughly 40% of Dell Technologies’ voting power, maintains a low public profile around his travel. The Madeira arrival follows a pattern of back-to-back flights from the New York area, where he keeps a $100 million One57 penthouse, and suggests a brief stopover before further movement. His Gulfstream G700, N6D, was also active in recent weeks, shuttling between Hawaii and Austin.