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Since Israel and the United States bombed Iran’s nuclear facilities in June 2025, President Donald Trump has vacillated between war, sanctions, and diplomatic negotiations in order to thwart Iran’s nuclear capabilities. Trump opened his second term by signing National Security Presidential Memorandum 2, which imposed maximum pressure on Iran as multiple rounds of indirect talks continued. In February, the U.S. and Israel struck Iran again, this time killing Supreme Leader Ali Khamenei and targeting nuclear and military infrastructure.

No U.S. missiles over the decades had ever directly struck the Iranian mainland itself.

A ceasefire followed within days, but subsequent fighting and failed attempts at diplomacy have made it impossible to sustain.

It is unsurprising that the Trump administration is struggling to reach a deal on nuclear proliferation with Iran that matches the scope of the 2015 Joint Comprehensive Plan of Action (JCPOA), more commonly called the Iran nuclear deal. President Barack Obama’s negotiators secured not just Iran’s cooperation but also Russia’s, China’s, and Europe’s to effectively and broadly secure U.N. Security Council authorization and policy. In return for JCPOA-related sanctions relief, Iran reduced its enriched-uranium stockpile by 98%, capped enrichment at 3.67%, and accepted expanded atomic monitoring.

Over the past three and a half decades, American presidents have created a system to pressure Iran that works through relationships with everyone but Iran.

Sanctions let presidents extract cooperation, concessions, and leverage on a variety of issues from other nations and corporations in the process. War extracts nothing from anyone but Iran.

The system of selective pressure against Iran took shape during the 1990s. After the Cold War came to a close, the George H.W. Bush and Bill Clinton administrations worked with Congress to forge a range of options short of war for handling Iran. American sanctions traditionally traced a simple logic: punish whoever sold Tehran weapons and the means to build them.

The first measures focused on proliferation. In the aftermath of the Iran-Iraq War, Congress worried that Tehran was rebuilding its military by acquiring sophisticated weapons and dual-use technology abroad. The 1992 Iran-Iraq Arms Non-Proliferation Act, signed by President Bush, made it U.S. policy to oppose transfers that could contribute to Iranian acquisition of chemical, biological, or nuclear weapons.

This law continued a convention of giving Washington a way to penalize weapons transfers without going to war, but its limits soon became apparent. Weapons sanctions could harm suppliers after the transfer, but they did not necessarily deprive Tehran of the money to purchase the technology or expertise in the first place.

By 1996, Congress went after ordinary trade. Congress and President Clinton increasingly viewed Iran’s energy sector as the financial bedrock that allowed Tehran to fund the actions Washington sought to deter. Rather than solely punish whoever supplied Iran with weapons, Congress sought to limit the revenue and investment.

The Iran and Libya Sanctions Act (ILSA) threatened any foreign company with complete exclusion from American credit, export licenses, and government contracts if it invested more than $40 million in Iran’s oil and gas sector — regardless of whether the company did anything weapons-related.

For the first time, ordinary commerce with Iran became a foreign relations trigger with the United States. The leverage was not a naval blockade, but access to the American economy itself.

The Russian-American relationship led to the testing and development of these new mechanisms. Washington and Moscow had three main issues over Iran: nuclear reactor technology and training, a multibillion-dollar natural gas field, and missiles.

The two governments did not have identical agendas. Americans wanted to prevent Iran from acquiring nuclear weapon expertise and missile technology, while also maintaining its relationship with Russia. Russians wanted to preserve valuable commercial and strategic ties with Tehran, including nuclear and energy contracts, without sacrificing its relationship with the United States.

They both aligned on a functional U.S.-Russian relationship with some limits on proliferation, but differed sharply over how much Russian cooperation with Iran was acceptable.

Nuclear reactors, gas, and missiles all received different political treatments. Classic diplomatic negotiations led to Russian President Boris Yeltsin agreeing to remove the uranium enrichment feature from Russia’s contract, even though the Bushehr reactor’s sale was legal under international law. As a light-water plant under International Atomic Energy Agency safeguards, it fell under the long-standing international nonproliferation treaty, leaving the United States unable to block the sale but still able to negotiate parts.

When Russia’s state-owned natural gas company Gazprom, alongside other international companies, sought a contract to develop the South Pars gas field, the largest natural gas field in the world, it put ILSA to its first real test. The $2 billion project involved several state-owned energy companies: France’s Total, Russia’s Gazprom, and Malaysia’s Petronas.

In response, Clinton issued a waiver for the international gas companies investing in Iranian energy. The administration pointed specifically to increased cooperation from the European Union on counterterrorism and nonproliferation to issue the waiver.

While the United States never formally used ILSA to sanction a company during this period, the atmosphere could then help the Clinton administration to negotiate with Russia on missile concessions.

Deputy Secretary of State Strobe Talbott captured the strategy in a sentence: “In a sense we are linking the two [missiles and energy], and in another sense we are not.” The vagueness was deliberate and useful for the differences in agendas on both sides.

Talbott pressed Russian Foreign Minister Yevgeny Primakov to blacklist Sanam, the Iranian missile entity attempting to acquire the technology, and the Russians did. Russia enacted new laws to pursue weapons and nuclear proliferation crimes, while increasing arrests and coordination between the FBI and Russia’s Federal Security Service. Clinton’s veto and the related tools gave American negotiators something to offer and Russia something to gain.

These policies helped the American-Russian relationship endure. Every waiver, every delay, every selectively enforced sanction since 1992 had been less a negotiation with Iran than a negotiation with someone else about Iran.

Waiving petroleum sanctions became the unspoken rule for the next 12 years. Until 2010, no American administration ever sanctioned a foreign company for investing in Iran’s energy sector.

The ILSA was renamed the Iran Sanctions Act (ISA) and expanded under the Comprehensive Iran Sanctions, Accountability, and Divestment Act in 2010 (CISADA); the Iran Freedom and Counter-Proliferation Act of 2012 (IFCA) toughened the consequences even more. These later acts added stricter enforcement measures and sanctioned major non-Western oil providers from China, Belarus, and Venezuela, while a special rule exempted allied companies in exchange for promises to halt investments.

By 2015, Washington could bargain with a sanctions system far broader than the ILSA. The JCPOA, or the Iran nuclear deal, either waived portions or removed designated Iranian institutions from the ISA, CISADA, and IFCA. The relief was substantial and conditional: Foreign firms and nations could again partake in specified oil, banking, shipping, and investment transactions with Iran while the underlying American statutes remained available if the bargain collapsed.

Meanwhile, sanctions tied to terrorism, human rights abuses, and ballistic missiles continued.

Discretion applied to war, as well. Bush considered strikes and held back for more nuclear enrichment proof. Obama rejected the military option as a matter of philosophy by arguing that war would buy less than diplomacy and cost the international coalition to enforce sanctions. Trump himself, in his first term, ordered a strike and called it off 10 minutes before execution, and Joe Biden sought to de-escalate. These four administrations had varying rationales and scenarios, but all were aligned in keeping force as a reserve option.

In his second term, Trump had access to the same policy options, including specific sanctions on industry sectors, supply-chain options laws, and relational pressure.

The lesson? A mix of pressure and exemption — not blanket coercion — worked. It allowed American presidents to lean hard on some part of a foreign nation’s relationship with Iran while tolerating others. Even the JCPOA, for all the criticism it drew, followed this strategy: it converted decades of accumulated third-party pressure into a deal. War trades a system built on the compliance of others for a strike that compels nothing from anyone but Iran itself.

Holly Harris is a doctoral candidate in history at Southern Methodist University, where she studies the collapse of the post-Cold War security relationship between the United States and Russia.

Made By History takes readers beyond the headlines with articles written and edited by professional historians. Opinions expressed do not necessarily reflect the views of The Inquirer.