The most striking feature of the memorandum Donald Trump signed with Iran is not what it contains but the shadow it casts backward. For years, Trump derided Barack Obama’s 2015 nuclear pact as “horrible” and a giveaway to Tehran. Now, his own framework is being measured against that very deal, and the comparison has become a political boomerang. Viewed from Washington, the president’s insistence that his agreement is superior rings hollow: critics across the partisan spectrum note he has secured far fewer verifiable restrictions while offering immediate, tangible relief that Obama only granted after painstaking verification.

What each document actually represents underscores the asymmetry. Obama’s Joint Comprehensive Plan of Action was a finished, 160-page accord narrowly focused on curbing Iran’s nuclear programme, with strict benchmarks, phased sanctions relief, and intrusive international inspections. Trump’s memorandum, by contrast, is a one-and-a-half-page, 14-point framework that launches a 60-day negotiation window. It is, in essence, a ceasefire agreement designed to halt a four-month war Trump initiated alongside Israel in February, a conflict that included the bombing of Iranian nuclear sites, a naval blockade, and the choking of the Strait of Hormuz. Where Obama pursued nearly two years of multilateral diplomacy with six other powers, Trump’s path was bilateral and preceded by military escalation that cost American lives and over $25 billion.

On nuclear matters, both texts contain a written Iranian pledge never to seek a weapon, yet the enforcement chasm is vast. Obama’s deal imposed tight limits on enrichment, extended the breakout time, and was backed by a rigorous IAEA inspection regime that confirmed compliance until Trump’s own withdrawal in 2018. The new memorandum outlines only a general path toward curbing nuclear activities, with no specific commitments beyond a promise to discuss the issue. It floats the possibility of down-blending near-weapons-grade uranium under international supervision but leaves any decision to a final accord that may never materialise. The sanctions architecture tells a similar story. Obama eased restrictions incrementally, only after a comprehensive settlement and verified steps. Trump’s framework front-loads relief: immediate waivers for Iranian oil exports, the unfreezing of billions of dollars in assets, and a vaguely sketched $300 billion development fund to be supplied by the US and its Middle Eastern allies. From Tehran’s vantage point, this is a windfall without preconditions; from London and European capitals, it looks like a reversal of the maximum-pressure logic Trump once championed.

The Strait of Hormuz provision crystallises the imbalance. The memorandum secures a reopening of the critical waterway through which a fifth of the world’s oil passes, but that is merely a return to the pre-war status quo, and the text suggests Iran will retain an administrative role after an initial toll-free period. Obama’s accord deliberately excluded such regional issues to keep the nuclear file manageable; Trump’s deal makes the strait a centrepiece yet delivers no permanent guarantee. Analysts in the Gulf note that Iran, which had kept the passage effectively closed since the war began, now extracts economic concessions for restoring what was always a norm of international commerce.

Looking ahead, the 60-day negotiation period is freighted with hurdles: sanctions architecture, enrichment limits, and the future of the strait must all be settled in a comprehensive pact. The risk, widely noted in Western capitals, is that Iran pockets the upfront relief while talks stall, leaving Washington with little leverage. The irony is acute: Trump, who for years excoriated Obama for returning $1.7 billion in frozen assets, now stands to facilitate a transfer of funds many times larger, with far fewer safeguards. Whether this framework becomes a genuine pathway to a durable settlement or a diplomatic cul-de-sac will depend on the coming weeks, but the early verdict from multiple geographies is that the dealmaker president has, for now, been out-negotiated by the very adversary he vowed to confront.