When Donald Trump illegally pulled out of the Iran nuclear deal in May 2018, he promised to secure a better arrangement through a policy of “maximum pressure” on the West Asian country. He did not get a better deal. Instead, Iran wrested back its bargaining chip by further increasing its enrichment of uranium.

Trump was, as Iran expert Trita Parsi argued, “given disingenuously bad advice” by his advisors, especially Mike Pompeo and John Bolton. According to Parsi, they “deceived Trump that escalating sanctions would bring Iran to its knees and enable Trump to secure a better deal while they knew all along that the strategy was designed to bring the US into war with Iran.” They misled Trump “into thinking that ramping up sanctions would break Iran and force it to capitulate to American demands.”

Instead of breaking Iran, US sanctions pushed it to reorient its trade and diplomatic relations. It turned to its neighbors, like Saudi Arabia, and looked east to China and Russia. Iran joined the Shanghai Cooperation Organization and BRICS, two massive international organizations whose goal is to counterbalance the American-led unipolar world. Iran also signed a 25-year strategic and economic partnership with China, as well as a Treaty on Comprehensive Strategic Partnership with Russia.

Iran didn’t capitulate to America: Iran turned away from America.

Now that Trump has returned to the White House for a second term, he faces a new president in Iran. Masoud Pezeshkian came to power on a promise of fixing relations with the US and even a policy of direct negotiations with no intermediary. But the Biden administration had spurned Iran’s opening, saying “we’re not in a position where we’re willing to get back to the negotiating table with Iran just based on the fact that they’ve elected a new president.”

Despite the inclusion of several Iran hawks in his cabinet, Trump now seems more open to negotiating with Iran. Last month, he declared that he “would love to be able to make a great deal” as long as “[t]hey cannot have a nuclear weapon.” He posted that he “would much prefer a Verified Nuclear Peace Agreement,” adding that “We should start working on it immediately.” In his address to congress on March 4, stunningly for an American president, there was no mention of Iran and no accusations of its support for terrorism or its destabilizing influence in the region.

On February 4, as Trump signed a presidential memorandum that, once again, called for maximum pressure sanctions on Iran, he did so reluctantly: “So this is one that I am torn about. I am signing this, but I am unhappy to do it.”

From Iran’s perspective, unhappy as Trump may have appeared, he still re-endorsed a policy of maximum pressure.

Once again, maximum pressure failed to bring Iran to the table. It did the opposite. Prior to the presidential memorandum, Pezeshkian had called for negotiations and Iran’s Supreme Leader, Ayatollah Ali Khamenei, had supported him. After the signing of the memorandum, Khamenei declared that “negotiating with such a government is neither rational, nor intelligent, nor honorable, and [we] should not engage in negotiations with it.” Pezeshkian reversed course, asking, “If the US were sincere about negotiations, why did they sanction us?” He insisted that Iran “will not yield to foreign pressure.”

America’s friends may want to pay closer attention to the strategy of America’s enemies. On March 5, Trump made good on his threat and signed an executive order imposing 25 percent tariffs on all imports from Canada and Mexico.

Canadians felt stunned and betrayed. In living memory, Canada has been one of America’s closest friends and allies. But Trump threatened Canada’s sovereignty, called the border between the two countries an “artificially drawn line” and threatened the use of “economic force.”

The ostensible justification for tariffs is to compel Canada to tighten border security to stop the flow of fentanyl into the US. But Canada accounts for only 0.2 percent of the fentanyl that enters America. Nonetheless, Canada was determined to work with the Trump administration, implementing a “$1.3 billion border plan” and appointing a fentanyl czar. Trump demanded results, and the Canadian response gave him the results he sought. On March 3, Canadian Prime Minister Justin Trudeau reported that “fentanyl seizures from Canada have dropped 97 percent between December 2024 and January 2025.”

Canada decided to work with the United States. The two countries are now in a trade war. Generations of friendship are destroyed. Favourable views of the US are now down 15 points from half a year ago, and, once unthinkable, 27 percent of Canadians now see the US as an enemy.

Engaging the US did not work for Iran: Trump unilaterally and illegally withdrew from the JCPOA nuclear agreement. Engaging the US did not work for Canada: it did everything the Trump administration asked for, virtually eliminating the fentanyl crossing the border; yet it will now feel the harsh pain of 25 percent tariffs.

Iran learned its lesson. “Our government at the time sat with them,” Ayatollah Khamenei reflected. “[A]n agreement was formed… However, the Americans did not honor that very agreement.” Iran reoriented their economic and foreign policy and turned to new partners.

Iran’s refusal to capitulate to American demands now seems to have produced results. Trump has signalled a readiness to talk. And on a February phone call, he asked Russian President Vladimir Putin to assist in “communicating with Iran on issues including the Islamic Republic’s nuclear program.” Russia responded that it is “ready to do everything in its power” to assist.

The irony is that the US has turned to one country that has successfully reoriented its trade policy from the West to the East in response to US maximum pressure sanctions to help negotiate with another country that has done the same.

Perhaps, with an emerging multipolar world awaiting them, America’s friends, like Canada, Mexico and the European Union, fresh off a failure to accommodate the US in a quest for a better deal, can learn a lesson from America’s enemies.

Ted Snider is a regular columnist on US foreign policy and history at Antiwar.com and The Libertarian Institute. He is also a frequent contributor to Responsible Statecraft and The American Conservative as well as other outlets. To support his work or for media or virtual presentation requests, contact him at [email protected].