Monday, June 8, 2026

In Negotiations With Iran, Trump Risks Repeating the Mistakes of Afghanistan

By Mike Nelson

Monday, June 08, 2026

 

Tell me if you’ve heard this one before. President Donald Trump is growing increasingly frustrated by a conflict with no clear end in sight. Despite initial overwhelming success and ongoing tactical victories against an enemy outmatched in skill and technological prowess, the war’s continuation has not brought the U.S. any closer to victory. His heart really isn’t in it, and he sees it as a distraction from the things he’d rather be focusing on.

 

Growing concerned about the costs of the conflict, Trump seeks a negotiated settlement to bring the fighting to a close. While this does seem like the most likely resolution to the war, our adversary proves to be a difficult and duplicitous negotiating counterpart. We find ourselves constantly offering concessions to our enemy—not as part of the final settlement, but just to convince its leaders to continue talks that they seem more than willing to walk away from. Our desperation to continue discussions is in part because, since the start of the negotiations, the enemy has avoided targeting American troops directly, instead continuing attacks on partners, allies, and their civilian infrastructure.

 

This constant pattern of concessions pulls America further and further from what we actually hoped to achieve in a settlement, and the act of negotiating becomes the goal in itself in hopes of getting a deal—any deal—that allows us to walk away from the war. Our nominal friends, Qatar and Pakistan, are offering questionable advice while pretending to act as honest brokers between the warring parties.

 

The situation above encapsulates the president’s current predicament as he seeks to end the war with Iran. But it is also a description of the first Trump administration’s approach to the Doha negotiations with the Taliban—a disastrous agreement that, while not the final conclusion to our longest war, almost guaranteed our embarrassing defeat.

 

First, let me concede there are obvious distinctions between the two conflicts. The duration and human toll of the war in Afghanistan both significantly outpace those of the war with Iran. Trump initiated the Iran war and will (hopefully) be the president who is ultimately responsible for its conclusion, whereas in Afghanistan, Trump inherited the ongoing conflict from two previous administrations, and he was not the commander in chief who oversaw the catastrophic end. His government, however, signed the agreement with the Taliban in 2020 that began the NATO withdrawal later that year and promised its completion by 2021. This timeline neither attributes sole responsibility to nor absolves Trump or Joe Biden of the disaster that followed with the 2021 fall of Kabul; as fellow Dispatch contributor Paul Miller has pointed out in his excellent book, there is plenty of shared blame among the four administrations that conducted the war.

 

But while there are distinctions between the two conflicts, there are also similarities specific to the Trump administration’s negotiating philosophy.

 

In 2017, President Trump announced his South Asia strategy—a plan for dealing with the war that had dragged on too long, with various shifting goals, nebulous end states, distracting mission creep, and too little focus on creating conditions for lasting stability in Afghanistan. Among other things, the strategy confronted a truth that many U.S. officials had been unwilling to face: We had not succeeded in ending the Taliban’s operations through military force, and were not likely to do so in the future. Therefore, there needed to be some plan for their reintegration into a post-conflict Afghanistan. The strategy envisioned reconciliation and the eventual political integration of the Taliban into the U.S.-backed Afghan government.

 

Yet to achieve this goal, American negotiators agreed to Taliban demands that planted the seeds of future disaster. The Taliban refused to allow the Afghan government to participate in the talks and made promises (that were never honored) to later negotiate directly with then-President Ashraf Ghani’s government only after a deal with Washington had been reached. In 2020, the U.S. agreed to the release of Taliban fighters in Afghan government custody—something Afghan officials were neither aware of prior to the deal nor supportive of, only doing so eventually, and begrudgingly, following U.S. arm-twisting. Their concerns proved legitimate: A large number of the thousands of fighters released then returned to the battlefield and participated in the final assault on Kabul in August 2021.

 

Today, the president seems to be walking down that same path, one where his need and desperation to keep negotiations going could lead him to agree to otherwise unacceptable terms—not even as part of a final settlement, but just for the potential for the other side to show up to the table.

 

Last week, the Iranians announced they were walking away from negotiations because of continued Israeli strikes against Hezbollah in response to rocket and drone attacks from the latter. Rather than take issue with this Iranian recalcitrance, Trump once again threw his ally under the bus. During an adversarial phone call with Benjamin Netanyahu, the president reportedly called the Israeli prime minister “crazy” for jeopardizing negotiations with Tehran. He then publicly claimed that he had gotten Israel to agree to the Iranian demands to halt hostilities in Lebanon, despite the fact that Hezbollah had given no such assurances.

 

If one of the White House’s stated goals for the war with Iran was severing the links between the Islamic Republic and its regional proxies, Tehran’s ability to demand protection for these militias, and the administration jumping to comply, do exactly the opposite—it codifies that connection.

 

Any extended protection over Hezbollah or other proxies in the final settlement would be unacceptable, as would any other conditions that run contrary to our stated goals. But rather than haggle over them in the process of diplomatic horse-trading, Iran is all but guaranteeing these conditions will be included by baking them in before the real negotiations happen. By making such demands preconditions for even talking, Iran preemptively weights the outcome, having notched a series of wins before we establish what is on the table regarding starting positions. It’s galling that a man who sold himself as a master dealmaker does not see or does not care how much he is willing to give away in advance.

 

The president is apparently spooked—both by the whispers that a settlement would be viewed as too sweet a deal for Iran and by the prospects of continued human costs, economic disruption, and depletion of critical military weapons if he were to reinitiate hostilities. So he commits to neither—doing anything to continue negotiations or maintain the appearance of negotiations and making repeated and increasingly far-fetched claims of a forthcoming deal. Perhaps he views this as Schrödinger’s negotiation, where all potential outcomes are possible and exist within the theoretical box as long as he never commits to one, keeping alive the hope of a glorious and undisputed victory.

 

But today, thanks to Trump’s missteps during the war, there are only outcomes with significant downsides within the box—and the drawbacks grow in number and severity the longer he dithers. In addition to waning public support for a military campaign that never enjoyed popular backing (primarily because the president never attempted to rally it), the president now faces growing congressional pushback, most recently in the form of a House measure to restrain the executive branch’s war powers. While the vote will prove largely symbolic, the fact that four Republicans joined Democrats is a sign of brewing bipartisan resistance to the president. 

 

As the president faces the headwinds of domestic opposition, he further narrows his range of options through public statements meant to calm markets spooked by the prospect of full-scale renewed hostilities. Not only is he conceding Iranian demands for extended protections for Hezbollah, but he is also casting off much of America’s leverage by implying he would not reinitiate offensive operations unless Iran kills more U.S. service members and signaling possible accommodations in nuclear negotiations. While there may be wiggle room to reach an agreement on these and other issues in a final deal, conceding them in advance removes them as levers to gain Iranian concessions.

 

Rather than continue his desperate overtures for diplomacy, Trump should take an approach similar to the one currently working in Iran’s favor and back away from talks until such a time as the Islamic Republic is willing to comply by engaging in good-faith negotiations and refraining from attacks on international shipping or civilian infrastructure. 

 

As Nick Catoggio notes, many observers continue to encourage the president to “finish the job,” including some who think regime change is still within the U.S. grasp. But ultimately, the burden, effort, and cost of overthrowing the Islamic Republic are well beyond the already demonstrated fleeting level of presidential interest. Insofar as Trump put any thought into the war’s outcome, the only real effort was his wishful and unrealistic plan that initial decapitation strikes in the first 24 to 48 hours would solve everything.

 

There are others, including me, who encouraged the president earlier in the conflict to at least achieve some quantifiable goal based on any of the objectives he enumerated at the start of the fighting. But since I made that case, America’s position has grown weaker through a combination of concessions, desperation, disinterest, naïveté, and neophyte bumbling from a president who never learned why the conflict with Iran has simmered for 47 years. So now, “finishing the job” may mean avoiding a truly disastrous deal and instead working to bring about a merely bad one. In his desire to avoid any blame or criticism for a negative outcome, Trump makes one in which there are conditions worthy of blame more likely—and fails to recognize the hard reality that the possibility of dodging well-deserved blame stopped existing long ago.

 

Ultimately, this war is going to end in a settlement, and sadly, because of the president’s decisions, it is likely to be a settlement that’s favorable to Iran. At a minimum, the outcome of the conflict will come with tacit recognition that the Iranians are the masters of a maritime chokepoint, with the ability to threaten the Strait of Hormuz at any time they choose, and that they got away with murdering tens of thousands of their own citizens—a grim signal to the Iranian people the next time they get notions about liberty, democracy, and human rights.

 

There will always be war between nations, and military force is a necessary tool in any president’s toolkit. Sometimes wars result in failure, despite the best planning and intentions of the governments that start them, or the incredible valor and skill of the soldiers who fight them. In this case, we have an abundance of the latter and a dearth of the former. For there are few things less forgivable than deciding to go to war without any willingness to invest the personal effort or political capital to win it.

 

In the end, whatever the specifics of the deal, this conflict will not prove to be the conclusion of a 47-year conflict, as the White House claimed in its ham-fisted communications at the war’s start. Rather, it will be just one chapter in the enduring clash between the U.S. and the Islamic Republic—one which makes the coming chapters more difficult than they needed to be.

No comments: