As a private businessman, Trump’s companies looked at Cuba in three waves. No hotel, casino, or golf course was built. He has always said he never closed a deal. 1998–1999 — first probe (Fidel Castro still in power) Trump Hotels & Casino Resorts paid consultant Seven Arrows Investment & Development at least $68,551.88 for work that included a trip to Havana. A Feb. 8, 1999 invoice billed the company for expenses “prior to and including a trip to Cuba on behalf of Trump Hotels.” Newsweek (2016), using that invoice, former executives, and court files, said the aim was hotels/casinos if the Clinton-era embargo loosened, and that Seven Arrows suggested tying the trip after the fact to a Catholic charity so it would look licensed. Sanctions lawyers later said OFAC would not have licensed a commercial scouting trip. web.archive.org/web/20201102… Trump’s line in 2016: “I never did anything in Cuba. I never did a deal in Cuba.” Kellyanne Conway said money was paid in 1998 but denied an investment. Roger Stone said consultant Richard Fields pitched Cuba and the casino-company CEO killed it. Seven months after the invoice, Trump published a June 1999 Miami Herald piece refusing European partners who wanted him to put casinos in Havana while Castro ruled. bbc.com/news/election-us-201… 2008–2010 — brand parking On 28 October 2008 the Trump Organization applied to register “TRUMP” at Cuba’s industrial-property office (lawyer Leticia Laura Bermúdez Benítez). Classes covered real estate/finance, golf and entertainment, hotels and restaurants. The mark was granted around 2010 and later lapsed/invalidated (term ran toward 2018). That is a placeholder for a future deal, not a project on the ground. bbc.com/mundo/articles/c4gv3… 2012–2015 — golf after Obama’s opening Bloomberg and others reported Trump Organization golf staff traveling to Cuba (sometimes described as golf or bird-watching). Donald Trump later told CBS Miami they “had some meetings.” Consultants circulated sketches of a possible Trump Tower Havana. Eric Trump publicly downplayed a business purpose. Again, nothing was built. theconversation.com/before-t… What did not happen No licensed U.S. hotel, casino, or golf resort. No public OFAC license for the 1998 trip. The embargo still barred most American commercial work with the Cuban state. Political timing The 1998 trip sat next to talk in Washington that the embargo might ease. The 2008 filing sat in the late Castro / early Raúl years. The 2012–15 visits sat after Obama’s December 2014 thaw. Once Trump was a candidate and then president, the public line was enforce the embargo—the opposite of those earlier scouting trips. Trump’s developer connections eyeing Cuba’s beautiful beaches for development should the Cuban government fall, hmm, that is what recent reporting describes, with an important split: some talks are happening while the current government is still in place, and some investors are openly planning for a collapse or U.S.-led opening. Why the beaches are suddenly empty of European brands In 2026 the Trump administration tightened secondary sanctions on Cuba’s military conglomerate GAESA and then on the tourism ministry. Spanish operators that had run the island’s best coastal hotels for decades pulled out: Meliá (34 hotels), Iberostar, Barceló, plus Canadian Blue Diamond. Those properties sit on Varadero, the cays, and Havana’s waterfront. The buildings and beaches are still there; the foreign flags are gone. nytimes.com/2026/06/04/world… Analysts in Spain and the U.S. have said the vacuum is exactly what U.S. chains (Marriott, Hilton, Hyatt, Wyndham) have wanted since the Obama thaw. Marriott already ran one Havana hotel in 2016–20. cubaheadlines.com/articles/3… People around Trump looking at that coastline 1. Dominari Holdings / former Trump Organization executives The Guardian (17 Sept 2026) reported that executives who once scouted Cuban real estate and helped register the Trump trademark in 2008 went back to Cuba in recent months under Dominari. Donald Trump Jr. and Eric Trump joined Dominari’s advisory board in 2025 and together own about 13.4%. Sources said the meetings were about hotel opportunities after Meliá and Iberostar left, and that the Cuban counterpart was Raúl Guillermo Rodríguez Castro (“El Cangrejo”), Raúl Castro’s grandson. Dominari did not comment. The paper does not say the sons sat in the room. theguardian.com/us-news/2026… 2. “Trump Island” on Cayo Santa María Dubai investor Ali bin Haidar signed a letter of intent with Cuban authorities for land on Cayo Santa María (white-sand cay east of Havana). Internal renderings shown to The National (Abu Dhabi) were twin gold-domed towers under a working name Trump Island. He said he had spoken to “the Trump office” and found it receptive. Cuba’s ambassador to the UAE said they saw no obstacle to talking business with Trump as a hotel/entertainment brand. No licensing deal has been announced. thenationalnews.com/business… 3. Texas allies on other assets, same logic The same Guardian piece describes Trump-world donors (Ray Washburne, Albert Huddleston) bidding for pieces of Canadian miner Sherritt after sanctions forced it out of nickel/cobalt. That is mines, not beaches — but it is the same pattern: sanctions empty a sector, friends of the administration line up for what comes next. quincyinst.org/2026/09/17/tr… What is not proven No public contract transferring a Cuban beach resort to the Trump Organization. No OFAC license for Americans to develop those sites today. “If the government falls” is the investors’ scenario, not a signed closing. Cuban officials are also shopping the same coastline to Gulf money without waiting for a collapse. How this sits next to the 1990s story The 1998 Havana scouting trip, the 2008 trademark, and the 2012–15 golf visits were the same product: hotels, casinos, golf, branded towers on Cuban sand. The 2026 version is that product plus a sanctions-created vacancy and a political bet that the island’s hotel stock will be re-let on American terms.

Brutal! Disgusting!

We are so screwed!

They want you to be tax slaves because you bought a home and until you sell your home!