President Donald Trump is setting deadlines for a deal with Iran while simultaneously beating the drums of war.

As a two-month nuclear deal deadline approaches, a fundamental question persists: What lessons can be drawn from the generational struggle spanning eight US administrations–four Democratic and four Republican? Can Trump take bolder, even unthinkable, steps than his predecessors? Whether he’s forging a new path or retracing old missteps could define not just his legacy, but the future of US-Iran relations.

History as a guide

Since 1979, US approaches to Iran have not only shifted from one administration to the next—they’ve often diverged within them, shaped by internal rivalries, changing regional dynamics, and evolving perceptions of Iran’s threat.

In the 1980s, President Ronald Reagan embodied this tension. His administration initially pursued covert diplomacy—most infamously through the Iran-Contra Affair—but later engaged in direct military confrontation in the Persian Gulf (Operation Praying  Mantis), a decisive clash towards the end of the Iran-Iraq War.

The 1990s brought a different posture under President Bill Clinton. Initially, his administration championed a “dual containment” strategy, targetting Iran and Iraq, and reinforced US naval presence in the Gulg by stationing the Fifth Fleet in Bahrain. But by his second term, Clinton had begun to soften his stance. In 1998, he offered a subtle diplomatic olive branch to Tehran, including an indirect apology aimed at opening channels with President Mohammad Khatami.

Then there was George W. Bush who initially explored cooperation after 9/11—particularly regarding post-Taliban Afghanistan—but soon shifted to military pressure, famously branding Iran part of the 'Axis of Evil' alongside Iraq and North Korea.

Then came President Obama, who attempted to reconcile pressure with engagement.  His administration imposed crippling sanctions during the presidency of Mahmoud Ahmadinejad while keeping “all options on the table.” Yet when Hassan Rouhani, a self-styled moderate, came to power, Obama pivoted to diplomacy. This ultimately led to the 2015 Joint Comprehensive Plan of Action (JCPOA).

But these shifting policies have often been hamstrung by internal divisions. The Carter administration was famously split between the hawkish Zbigniew Brzezinski and the diplomacy-focused Cyrus Vance, resulting in an inconsistent Iran policy. This division ultimately contributed to the failure to resolve the 1979 -1981 American Embassy hostage crisis through either diplomacy or military action.

The Bush administration saw similar tensions, with hawks like Dick Cheney and Donald Rumsfeld clashing with doves like Colin Powell. Powell, for instance, told reporters he was open to exploring opportunities with Iran “without having any Vaseline in our eyes, with respect to the nature of the government or the history of the past 22 years.”

Though the Trump administration may appear more ideologically unified, it too shows signs of internal conflict.

Vice President J.D. Vance has warned against escalation, stating, “War with Iran is not in the US interest.” Meanwhile, Secretary of State Marco Rubio is reportedly pressing for tougher action, against the backdrop of shifting geo-politics in the Middle East that didn’t exist months ago. Trump himself remains a wildcard, alternating between anti-war populism and hawkish bravado. Having vowed to end America’s “forever wars”, he now flirts with launching a new one with Iran. Does he truly know whether he wants to negotiate—or escalate?

Three possible paths

Over the past 46 years, US strategies toward Iran have generally fallen into three broad categories: containment and sanctions, military pressure, and diplomacy.

The first and most frequently deployed approach has been economic containment. From Clinton’s “dual containment” to Obama’s “crimpling sanctions,” successive administrations have sought to isolate and pressure Iran economically.  

These measures have undeniably hurt Iran’s economy and limited its global reach. However, they have largely failed to bring about lasting change in Iran’s foreign policy or internal governance.  At best, such pressure has helped usher in reformist governments willing to engage—suggesting that while sanctions can influence internal dynamics, they do not guarantee transformation.

The second strategy has been the use of military pressure or limited force. This has produced mixed and often unpredictable outcomes.

President Carter’s failed 1980 hostage rescue mission remains a cautionary tale in operational outreach. In contrast, Reagan’s 1988 naval strikes in the Persian Gulf, pressured Iran into accepting a ceasefire with Iraq—an outcome so bitter that Ayatollah Khomeini likened it to “drinking poison.”

More recently, Trump’s maximum pressure campaign, including the assassination of General Qassem Soleimani, significantly escalated tensions but failed to convince Iran into substantive negotiations.

Instead, it deepened Tehran’s distrust and provoked direct retaliation.

Diplomacy, the third path, has shown glimpses of promise—though its gains have often been short-lived.

After 9/11, Iran played a constructive role in the US-led initiative against Afghanistan. At the 2001 Bonn Conference, US envoy James Dobbins praised Iranian involvement stating, "No delegation was as helpful as the Iranian one." He emphasised that without the Iranians, the formation of Hamid Karzai’s government might not have occurred.

Over a decade later, diplomacy again bore fruit with the JCPOA, marking a high point in direct engagement. Yet, this deal was narrow in scope and unravelled quickly, underscoring the vulnerability of diplomatic gains when broader consensus and continuity are lacking.

The thinking unthinkable

But there remain two potential strategies that are largely unexplored.

First, no US president has seriously considered overthrowing the Iranian regime through military force. George W. Bush came closest, following the swift occupations of Afghanistan and Iraq, and with the infamous remark from a senior Bush official, "Anyone can go to Baghdad. Real men go to Tehran," reflecting the post-Iraq invasion hubris. 

Second, no US administration has ever engaged in a comprehensive grand bargain with Iran—a deal that addresses not just nuclear issues but Iran’s regional role, missile program, and relations with Hezbollah and Hamas. Past negotiations have been issue-specific and narrowly scoped.

With Iran at its weakest, could Trump, with his transactional mindset and desire to achieve the unprecedented, pursue a comprehensive agreement? His political DNA is defined by a drive to accomplish the impossible. As he stated in his inauguration speech, "In America, the impossible is what we do best."

There are signs—however faint—that Tehran might be receptive.

Recently, Iranian Vice President Javad Zarif wrote in Foreign Affairs that President Masoud Pezeshkian is open to “equal-footed” negotiations on the nuclear deal and beyond — potentially a subtle invitation for a broader agreement. The US is also reportedly weighing indirect nuclear talks, even as military tensions rise in the region.

While these signals remain cautious, they open the door — however narrowly — for a more comprehensive dialogue.

This would not be without precedent. In 2003, then-President Mohammad Khatami, with the backing of Supreme Leader Ali Khamenei, proposed grand talks via the US via the Swiss ambassador — a rare offer that included Iran’s nuclear program, support for militant groups, and its role in the region. The Bush administration summarily rejected it.

American presidents have long misread Iran—viewing pressure as a shortcut to change. In 2003, the Bush administration dismissed an opportunity for engagement, betting instead on regional upheaval to reshape Tehran. That gamble failed.  

The question remains: Will Trump grab the chance to pursue a grand strategic realignment to reshape US-Iran relations—or will he reinforce the same illusions that have guided Washington since 1979?