1290 Avenue of the Americas (30% Stake)

Trump holds a 30 percent interest in this 43-storey Midtown Manhattan office tower, originally designed by Emery Roth and Son in 1964 and restored in 2013. The stake is held through a joint venture with Vornado Realty Trust, led by Steven Roth, who served on Trump's economic advisory council. With the property carrying approximately $950 million in debt, Forbes estimates Trump's net share at around $137 million. The deal originated from a property swap involving Riverside South — considered one of the most lucrative transactions of Trump's career. When Vornado hedged its interest-rate risk during refinancing, Trump did not, reportedly resulting in multimillion-dollar losses.