Iran appears to have assembled most of the visible elements of a new security architecture in the Persian Gulf. The military balance, a proposed maritime administration, negotiations with Oman and a mechanism for controlling commercial passage through the Strait of Hormuz are all taking shape. The outstanding question is increasingly political: what will it take for Donald Trump to be pragmatic?
Iran and Oman say they have reached fundamental understandings on a new navigational arrangement. Under proposals described to Reuters, Iran would exercise authority over vessels entering the Persian Gulf, while outbound vessels would follow an Iran-Oman arrangement. Tehran has established a Persian Gulf Strait Authority and is proposing charges associated with passage, although the size and legality of those fees remain fiercely disputed. The shipping and insurance industries have also warned that the current proposal conflicts with sanctions and existing insurance arrangements.
The underlying strategic reality, however, has proved remarkably resistant to military pressure. The United States still maintains its blockade on shipping entering or leaving Iranian ports, while Iran continues to exercise effective control over passage through Hormuz. Reuters reported this week that months of American military operations have failed to break Iran's grip on the strait. Iran and Oman have meanwhile agreed on the coordinates of a prospective route and Tehran says reopening remains conditional on Washington returning to its earlier commitments.
In other words, everyone increasingly appears to be waiting for Trump.
Understanding how Trump might interpret such an arrangement makes renewed interest in his relationship with Roy Cohn particularly timely. A major new profile, The New Yorker's “The Mentor,” examines how Cohn influenced Trump as a young New York property developer. Its significance is less a psychiatric diagnosis of Trump than an examination of the negotiating habits he developed.
Cohn taught Trump to fight publicly, dominate the narrative and never willingly appear to have lost. Trump himself explained that he preferred fighting to folding because once somebody acquired a reputation for folding, opponents would exploit it. Yet one episode described in the article reveals something more interesting about Trump's psychology. In the 1970s discrimination case against Trump Management, Trump and Cohn fought spectacularly and publicly for nearly two years—before Trump eventually agreed to a settlement resembling one available much earlier. He paid no fine and admitted no guilt. He and Cohn then publicly characterized the outcome as a victory.
That distinction could matter at Hormuz. Beneath Trump's highly confrontational rhetoric has historically existed considerably more transactional flexibility. The important requirement may not always be achieving everything originally demanded, but constructing an outcome that Trump can credibly present as a successful deal. As Roger Stone described Trump's approach in the Cohn profile, improvisation became one of his great strengths.
There is another dimension to Trump which receives increasing attention: businessman Trump and the extraordinary diversification of his family's commercial interests.
The family's traditional property, golf and licensing operations have now been supplemented by cryptocurrency businesses. Trump's 2025 financial disclosure reported more than $1.4 billion of income from family crypto ventures, including almost $800 million associated with World Liberty Financial and $635 million from Trump meme-coin sales. Reuters separately estimated that the Trump family has earned at least $2.3 billion from crypto projects since his return to office in 2025.
The international connections are equally notable. An Abu Dhabi investment company, MGX, made a $2 billion investment in Binance using World Liberty's USD1 stablecoin. The Trump Organization has also continued expanding its international property-licensing activities, including projects in the Gulf.
These arrangements have inevitably attracted political scrutiny because Trump's public office and private family interests coexist. That scrutiny should nevertheless be described accurately. Critics argue that foreign investment creates potential conflicts of interest; Trump and his businesses reject accusations of impropriety. Similarly, Capital One recently disclosed that an anti-money-laundering review preceded its closure of more than 300 Trump-affiliated accounts in 2021, but the bank specifically has not accused the Trump Organization of money laundering. The Trump Organization and Eric Trump have argued that the closures constituted politically motivated “debanking.”
Perhaps this is the more useful lens through which to view the coming Hormuz decision. Trump may dislike the appearance of conceding Iranian control after promising something very different, but his history also demonstrates an ability to transform an adversarial situation into a transaction and then sell the resulting compromise as victory. He does not necessarily need Iran to surrender. He needs a deal he can own.
Trump is, ultimately, a pragmatic, creative and wise businessman who has been very successful and, given the hostile political environment in the United States, would understandably want to ensure that his family has a variety of income sources after he passes. The question at Hormuz is whether that same commercial pragmatism can now turn an extraordinarily dangerous strategic confrontation into a deal.