Machiavelli's advice to Trump about Iran
Analysis, not advocacy. Facts through late September 2026.
The situation as it now is
There is no longer only a long cold confrontation. There has been war.
After the 2018 collapse of the JCPOA, maximum pressure, Soleimani, proxy attacks, the April 2024 Iranian barrage on Israel, and years of 60 percent enrichment, the next phase began in June 2025: when a U.S. deadline for a nuclear deal expired, Israel struck and the United States joined with bunker-busters on Fordow, Natanz, and Isfahan (Operation Midnight Hammer). Enrichment was badly damaged; IAEA access shrank further.
On 28 February 2026 the United States and Israel opened a larger campaign (Epic Fury / Roaring Lion). Aims included missiles, navy, nuclear reconstitution, proxies, and, at first, regime change. Ali Khamenei was killed; Mojtaba Khamenei was named successor and has barely appeared in public. An April ceasefire flickered. On 17 June 2026 Trump signed the Islamabad Memorandum at Versailles and Pezeshkian signed in Tehran: reopen the Strait of Hormuz, talk for sixty days on nuclear issues, missiles, and sanctions. Iranian attacks on shipping in early July killed the ceasefire. The United States struck back and reimposed a naval blockade. The memorandum lapsed on 17 August with no final deal.
As of the last days of September 2026 the two sides are again trading limited blows—Iranian attempts on U.S. ships, U.S. hits on tankers and coastal sites—while mediators shuttle. Iran offered a seven-day Hormuz reopening plus later nuclear talks in exchange for lifting the blockade, some frozen funds, oil waivers, and a “ceasefire on all fronts,” including Lebanon. Trump rejected the sequencing. Officials say he will grant some sanctions relief only for concrete nuclear steps; he has also said Tehran “overplayed its hand.” U.S. costs are in the mid-tens of billions; U.S. dead are in the high teens; Iranian dead, including civilians, are in the thousands. Iran still holds a large share of mobile missile launchers and is rebuilding underground. Reconstruction signals have appeared at Parchin. Bushehr units 2 and 3 continue under Rosatom. Midterms are five weeks away.
The problem is no longer “how to deter a threshold state.” It is how to end an unfinished war that produced neither surrender nor a bargain that survives contact with the IRGC.
Machiavelli’s lens
The same books apply—The Prince and the Discourses
Appear peace-seeking while keeping your own arms ready (chs. 18, 12–14, 21).
Public restraint and openness to talks; private readiness. Reputation for moderation deters without fusing every enemy against you. That posture is harder after you have already used the B-2s and then signed a memorandum that died in a month.
Use your own arms; do not let auxiliaries write the war (chs. 12–13).
Israel’s interests overlap yours; they are not the same. Hezbollah, Lebanon, and existential nuclear fear will pull the calendar toward Jerusalem. A prince who cannot set timing and scope owns the political costs and lets the ally pocket the gains.
Do not make threats you will not keep; do not dribble injuries (chs. 17, 21, 8).
Red lines must be few and enforced. Cruelty well used is done once, for a political object, then stopped, with an off-ramp visible. Cruelty badly used leaks out for months, kills civilians without changing the regime’s will, spends munitions you cannot quickly replace, and teaches the other side that time—and your election—is their ally.
Be feared enough to deter; avoid hatred (chs. 17, 19).
Hit capabilities, not the Iranian street in word or deed. Fear deters. Hatred unites the regime, feeds succession hard-liners around Mojtaba, and rots consent at home.
Do not begin a conquest you cannot hold (ch. 3).
Louis XII took Milan and then made every subsequent error: he strengthened a rival, did not settle among the inhabitants, and let others dictate the sequel. Killing a supreme leader, cratering enrichment, then trading a vague sixty-day paper for the appearance of peace is the modern half-conquest. Either you consolidate—inspectors in, stockpile accounted for, snapback real—or you admit you have only wounded the enemy and you keep the remaining instruments of pressure.
Never empower a rival you cannot later restrain (ch. 3).
Do not lift the last sanctions and the blockade for modest nuclear leftovers after the 2025 strikes already destroyed much of the program. Those tools are now your own arms. Construct every exemption so it can be clawed back in hours, not months.
Keep enemies divided (Discourses I; Prince ch. 3).
A wounded theocracy in succession is more dangerous this season and more divisible the next. IRGC, pragmatists, provincial elites, and proxies with local wars do not want the same things. Inducements should go only to factions that can deliver restraint.
Benefits slowly, punishments swiftly (ch. 8).
Relief in small, reversible slices. If you strike, strike, stop, and show the ladder down. A memorandum that evaporates trains Tehran to treat American paper as weather.
The people are the fortress (chs. 19–20; Discourses I).
Energy spikes, drawn-down magazines, and a war that looks neither won nor ended before an election are how a prince becomes hated without remaining feared. Narrow the public aim: no nuclear weapon, open navigation, troops alive. “Unconditional surrender” one month and “they can keep some missiles” the next is read as weakness.
Fortune favors the bold whose boldness was prepared (ch. 25).
The river metaphor: dikes are built in quiet weather. Energy buffers, munitions, maritime coalitions, and backchannels should have been finished before February. Buying them now, while fighting and campaigning, is paying retail.
A broken bargain damages reputation more than no bargain (chs. 18, 21).
The fox may break faith when necessity requires. He must not become known as a man whose memoranda last four weeks. The next instrument must be shorter, more verifiable, and paired with a snapback you will actually use. Repeating “we will bomb them if they violate” after they have already violated is not virtù.
A playbook for this standoff
- Name the war you are in. Limited interstate war. Object: no nuclear weapon, open strait, degraded attack infrastructure, regime isolated from its people. Drop regime-change language you will not resource.
- One sequencing rule, written. Nuclear verification—inspectors on the wreckage, disposition of the 60 percent stock, no covert rebuild—moves in lockstep with maritime relief. Hormuz first, Fordow later is the substance of the offer you were right to refuse.
- Make the next paper self-executing. Incremental licenses, automatic snapback, no sixty-day fog. No grand peace that the other side can pocket.
- Keep Israel close and subordinate to your clock. Share intelligence. Do not outsource the decision to reopen a major air campaign, especially before U.S. elections. Lebanon fighting almost wrecked the last track; it will try again.
- Strike the purse and the reconstitution, then stop. Revenue nodes, missile production, enabling materiel. Civilian infrastructure as punishment converts fear into hatred and hands Mojtaba a story.
- Speak softly in public; be unmistakable in private. Public: a deal that lets Iran rebuild a greater country if the nuclear file is real. Private: the blockade and remaining sanctions stay until inspectors walk the sites. Intermediaries (Oman, Qatar, Pakistan, Switzerland) carry both the warning and the ladder.
- Treat the midterms as a military fact. Looking eager to resume bombing after November tells Tehran to stall. Either close a narrow bargain now or budget endurance as if delay is their strategy—because it is.
- Do not trade the last coercive tool for the remnant of a program you already hit. Stage sanctions relief. Do not dump it for talks.
- Widen seams inside Iran; do not fuse them. Tailored, reversible inducements for anyone who can deliver restraint. Spotlight it when it appears. Do not fund the center that only cashes the check.
- Preserve domestic endurance. Explain the aim as deterrence, nonproliferation, and navigation—not annihilation one week and reconstruction the next. Pre-arrange energy and shipping contingencies so a closed strait does not become a domestic revolt against the prince.
What this means for you, in his idiom
You have already used the lion. The scarce virtue now is the fox: a short, enforceable bargain that does not give back the leverage the bombs bought.
You issued maximalist lines—unconditional surrender, take over your government—and then walked them. That is how contempt is taught. Issue fewer.
A memorandum that dies in four weeks is worse than no memorandum. The next one must be smaller and harder.
Hormuz is leverage only while you still hold it. Trading the strait for a promise to talk about enrichment is how Louis lost Milan.
Fortune favored the 2025 nuclear strike. Fortune will not favor a six-month war of diminishing returns into an election. Prepare the dikes or get off the river.
Project the peacemaker forced to be firm. Seek talks. Keep decisive options ready and unused unless a clear, written demand is refused. Strike capabilities that enable attacks; stop when the message is sent; reopen the door. Reward restraint in slices. Keep partners close and your choices sovereign. Let intermediaries carry both the threat and the offer so the other side always has a ladder down—and so you are not the man who promised a peace he could not hold.