Trump Shares Awkward Throwback Photos for Self-promotion

WHO:

The Daily Beast - Donald Trump, President of the United States

Yahoo - Donald Trump, President of the United States

The Daily Beast - Fred Trump, Donald Trump's father

The Daily Beast - John D. Miller, former chief marketing officer for NBC

WHAT:

The Daily Beast - Trump posted self-promoting messages on Truth Social.

Yahoo - Trump posted throwback photos of himself, including one from a 1986 cover of Fortune magazine.

The Daily Beast - Trump took charge of the Wollman Skating Rink in Central Park in 1986.

The Daily Beast - Trump filed for corporate bankruptcy six times, including for several casinos.

The Daily Beast - Trump paid $25 million in 2016 to settle two federal class-action suits and a civil suit by the New York Attorney General.

The Daily Beast - Trump agreed in 1998 to pay $1.375 million to settle a labor class-action lawsuit.

WHERE:

The Daily Beast - Central Park, New York City, New York

The Daily Beast - Atlantic City, New Jersey

The Daily Beast - Bonwit Teller building, Manhattan, New York

WHEN:

The Daily Beast - Trump took charge of the Wollman Skating Rink in 1986.

The Daily Beast - The contract for the Wollman Rink was awarded to another operation in 2025.

The Daily Beast - Trump paid $25 million in 2016.

The Daily Beast - Trump agreed to pay $1.375 million in 1998.

WHY:

The Daily Beast - Trump posted messages to promote his image as a capable and successful individual despite current national issues.

HOW:

The Daily Beast - Trump used Truth Social to share his messages and photos.

(UPDATED June 14, 2026 17:20 UTC)

Trump recently took to Truth Social to share self-promoting messages and throwback photos, including one from a 1986 cover of Fortune magazine. In his posts, he highlighted his past achievements, such as taking charge of the Wollman Skating Rink in Central Park and settling various legal disputes, including a $25 million payment in 2016. This effort seems aimed at reinforcing his image as a capable and successful individual amid ongoing national challenges.