The Boeing 757 has long been a fixture in the world of VIP aviation, standing alongside more famous widebody jets like the Boeing 747 that have served as symbols of luxury and power for governments and private owners. Among these, one particular aircraft—a Boeing 757-200 registered as N757AF—has become widely recognized due to its association with former U.S. President Donald Trump.
Trump's involvement with large aircraft began in 1989 when he acquired part of Eastern Airlines and created Trump Shuttle, which operated a fleet of Boeing 727s between major East Coast airports. Although he invested heavily in upgrading these planes, the business struggled financially and was sold off by 1992. Trump retained one of the Boeing 727-100s for personal use, converting it into a VIP jet with high-end interiors and amenities. However, by the early 2010s, maintenance costs for the aging plane led him to seek a replacement.
In 2010, Trump purchased his current Boeing 757-200 from Microsoft co-founder Paul Allen for a reported $100 million. The aircraft had previously flown for Sterling Airways and TAESA before Allen converted it into a VIP jet. Upon acquisition, Trump commissioned Eric Roth to redesign the interior at an additional cost of $37 million.