By: Ken Robinson
Fifty years ago, I entered the U.S. Army Rangers, shaped in no small part by the shock of the 1972 Munich Olympic massacre. That decision set me on a path through military intelligence, Special Operations, and the shadow world of covert and clandestine support to U.S. missions overseas.
It brought my attention to the Palestinian question, and Iran.
The span between then and now feels less like a lifetime than a shutter click. It begins with the fall of Saigon in 1975, the chaotic end of a decade-long war, and runs forward to the equally disordered evacuation of Afghanistan in 2021, closing twenty years of the Global War on Terror.
Two different conflicts, two different eras, but strikingly similar endings.
Along the way, there were undeniable tactical successes. Operations executed with precision. Networks disrupted. Targets found and fixed. But the strategic outcomes are harder to defend. The underlying conditions that gave rise to these conflicts were never fully resolved, only managed, deferred, or displaced.
That raises a harder question - one that policymakers and practitioners are still grappling with:
How did a half-century of continuous engagement, investment, and sacrifice leave us once again at the edge of a widening regional conflict, with escalation risks that could extend far beyond their point of origin?
And more importantly - what, if anything, have we learned in fifty years that would prevent us from continuing to repeat the same cycle?
“Insanity is doing the same thing over and over again and expecting different results.” Einstein
As we sink deeper into a major regional conflict (MRC) in the Middle East, we find ourselves trapped in a perpetual loop, in a conflict that has been built - deliberately, incrementally, and often unintentionally - over fifty years of policy decisions that prioritized immediate tactical gains over long-term strategic stability.
What exists today is not a crisis in the traditional sense. It is a system of an industrial complex of war, that transcends republican or democratic administrations. A system of persistent conflict, proxy warfare, strategic ambiguity, and unresolved political grievances that has hardened across decades.
It is adaptive. It is durable. And it is increasingly resistant to conventional deterrence.
To understand the present, one must move deliberately through the past, away from our own cultural geopolitical amnesia: Why Iran, why now?
THE 1970s - KISSINGER AND THE ARCHITECTURE OF MANAGED INSTABILITY THRU STRATEGIC AMBIGUITY
Strategic ambiguity is a deliberate policy in which a state intentionally leaves its intentions, thresholds, or responses unclear in order to influence the behavior of adversaries, allies, or competitors without committing to a fixed course of action.
Or, as any Arab leader would define it: LIES.
At its core, it is the controlled uncertainty used as a tool of statecraft.
Following the 1973 Yom Kippur War, U.S. Secretary of State Henry Kissinger pursued what he viewed as a realistic approach to Middle East stability. Rather than attempting to solve all underlying disputes - particularly the Palestinian question - he focused on preventing another large-scale Arab-Israeli war.
His method was deliberate fragmentation.
Through shuttle diplomacy, Egypt under Anwar Sadat was separated from Syria and the broader Arab coalition. This reduced the likelihood of a unified military front against Israel. It also secured a strategic victory for U.S. interests in the Cold War context.
But the cost was structural.
The United States chose to manage tensions rather than resolve them. Palestinian statelessness remained unaddressed. Arab political cohesion fractured. Regional grievances were contained, not settled.
This strategic ambiguity, created a system in which instability was controlled but never eliminated. Over time, that instability migrated from state actors to non-state actors.
THE 1979 SHOCK - REVOLUTION AND HOSTAGE CRISIS
The Iranian Revolution shattered the existing regional order.
The fall of Shah Mohammad Reza Pahlavi removed a central pillar of U.S. strategy. Ayatollah Ruhollah Khomeini established a theocratic regime النظام built on resistance to Western influence. The creation of the Islamic Revolutionary Guard Corps (IRGC) institutionalized a new doctrine: ideological warfare fused with asymmetric capability.
Then came the defining rupture.
On November 4, 1979, Iranian militants seized the U.S. Embassy in Tehran. Fifty-two Americans were held hostage for 444 days.
This event reshaped American politics.
President Jimmy Carter’s administration became defined by the crisis. The failed rescue attempt, Operation Eagle Claw, reinforced a perception of American weakness. The prolonged nature of the crisis eroded public confidence in U.S. leadership.
Domestically, it contributed directly to Carter’s electoral defeat and the election of Ronald Reagan, who campaigned on restoring strength and credibility.
Strategically, the hostage crisis transformed U.S.-Iran relations into a condition of enduring hostility.
THE 1980s - WAR, ADAPTATION, AND THE CREATION OF THE PROXY MODEL
The Iran-Iraq War (1980-1988) became the laboratory for Iran’s long-term strategy.
Facing Saddam Hussein’s military, which was supported by the United States covertly, Iran adapted under pressure. It developed a doctrine built on endurance, ideology, and asymmetry.
Human wave assaults, martyrdom narratives, and decentralized command structures were not merely desperate measures. They were innovations that allowed Iran to compensate for conventional weakness.
At the same time, Iran began exporting its model.
In Lebanon, the IRGC helped establish Hezbollah. Under leaders such as Hassan Nasrallah, Hezbollah evolved into a disciplined hybrid force combining governance, ideology, and military capability.
The 1983 bombing of the U.S. Marine barracks in Beirut, which killed 241 Americans, demonstrated the strategic power of proxy warfare. A non-state actor, backed by a state, had forced a superpower to reconsider its presence.
This was a turning point. Proxy warfare had proven its effectiveness.
THE 1990s - TEMPORARY STABILITY, PERMANENT FRAGILITY
The 1991 Gulf War achieved its immediate objective: the expulsion of Iraqi forces from Kuwait. However, the decision not to remove Saddam Hussein left Iraq weakened but intact.
Throughout the decade, the United States pursued containment. Sanctions, no-fly zones, and limited engagement defined policy.
Iran used the time differently.
It refined Hezbollah into a long-term model of influence. It demonstrated that proxies could be sustained indefinitely, embedded within societies, and used to apply pressure without triggering full-scale war.
Meanwhile, Palestinian unrest erupted into the Intifadas. Suicide bombing became a normalized tactic, further embedding asymmetric warfare into the regional conflict landscape.
THE 2000s - 9/11 AND THE STRATEGIC CONSEQUENCES OF IRAQ
The attacks of September 11, 2001 forced the United States into a global war posture.
The invasion of Afghanistan removed the Taliban regime. Iran initially saw alignment with U.S. objectives but quickly shifted to a hedging strategy. Tehran ensured that U.S. forces would remain tied down, with an endless supply of lethal aid to the Taliban and fighters to kill americans.
Iran introduced explosively formed penetrators - highly advanced IEDs capable of penetrating U.S. armored vehicles. These weapons significantly increased American casualties and altered the tactical environment.
U.S. Casualties from Iran supplied IEDs
Iraq and Afghanistan Wars (2001–2021)
Iraq War (Iraq War)
Killed (KIA from IEDs):
Approximately 2,700 – 2,800 U.S. personnel
Roughly 60–65% of all U.S. deaths in Iraq
Wounded (WIA from IEDs):
Approximately 20,000+ wounded
Includes blast trauma, amputations, burns, and traumatic brain injury (TBI)
Operational context:
IEDs became the primary insurgent weapon by 2005–2007
Responsible for the majority of casualties during peak insurgency
Triggered rapid U.S. adaptation: MRAP vehicles, route clearance units, electronic jamming
Afghanistan War (War in Afghanistan)
Killed (KIA from IEDs):
Approximately 1,000 – 1,100 U.S. personnel
Roughly 50–55% of all U.S. deaths in Afghanistan
Wounded (WIA from IEDs):
Approximately 10,000 – 12,000+ wounded
Operational context:
Taliban relied heavily on Iranian low-metal, pressure-plate IEDs
Difficult to detect; high lethality in dismounted patrol environments
Became the defining tactical threat of the war’s later years (2009–2013 surge period)
Combined Total (Iraq + Afghanistan)
Killed (IED-related):
~3,700 – 3,900 U.S. personnel
Wounded (IED-related):
~30,000 – 32,000+ U.S. personnel
The 2003 invasion of Iraq fundamentally altered the balance of power.
By removing Saddam Hussein, the United States eliminated Iran’s primary regional adversary. Iraq transitioned into a Shia-led political system, increasingly aligned with Tehran.
Iran moved decisively.
Through the IRGC-Quds Force, led by Qasem Soleimani, Iran embedded itself within Iraqi political structures, security forces, and militias. Organizations such as Kataib Hezbollah became instruments of Iranian policy.
Simultaneously, Syria facilitated foreign fighter flows into Iraq. These networks sustained the insurgency.
The United States found itself engaged in a conflict environment shaped by both state and non-state adversaries operating in parallel.
THE 2010s - EXPANSION OF THE BATTLESPACE
The Stuxnet cyber operation marked a new domain of warfare. Cyber capabilities were now capable of physical destruction of Iranian nuclear fuel production.
The Arab Spring destabilized multiple regimes. In Syria, Bashar al-Assad faced a widespread uprising. Iran intervened decisively, deploying resources and proxy forces to preserve the regime.
The Syrian Civil War became a multi-layered conflict involving regional and global actors.
From this instability emerged ISIS, a direct product of state collapse and sectarian fragmentation.
The 2015 Obama era nuclear agreement (JCPOA) sought to constrain Iran’s nuclear program. It succeeded in imposing temporary limits but did not address Iran’s proxy network.
Joint Comprehensive Plan of Action (JCPOA):A multilateral agreement designed to restrict Iran’s nuclear program in exchange for sanctions relief, with the objective of preventing Iran from developing a nuclear weapon.
This created a structural imbalance. Nuclear risk was reduced in the short term, while regional influence continued to expand.
THE 2020s - SYSTEM RESILIENCE AND GLOBAL EXPANSION
The killing of Qasem Soleimani in 2020 removed a central figure in Iran’s network. However, it did not dismantle the system. Iran adapted by decentralizing further.
Israel intensified its covert operations, targeting Iranian scientists and infrastructure.
Iran expanded its proxy operations into new domains.
Houthi attacks on Red Sea shipping represent a critical shift. Proxy warfare now directly threatens global economic systems. Supply chains, energy flows, and maritime commerce are all exposed.
ANALYTICAL SYNTHESIS
Over five decades, two distinct strategic approaches emerged.
The United States:
Focused on immediate objectives, crisis management, and tactical victories.
Iran:
Focused on continuity, network-building, and long-term pressure.
This asymmetry has produced the current system.
THEN RUSSIA INVADED UKRAINE
The war in Ukraine has evolved into a revealing case study of modern proxy-enabled warfare, where industrial gaps, sanctions pressure, and geopolitical alignment have fused into a mutually reinforcing partnership between Russia and Iran. What began as a battlefield deficiency for Moscow has matured into a structured military-industrial and financial relationship that now sustains Russia’s war effort and expands Iran’s strategic reach.
IRAN’S DRONE WAR IN UKRAINE: FROM STOPGAP TO CORE CAPABILITY
Russia entered the Ukraine war with a critical vulnerability: an insufficient supply of precision-guided munitions and a limited domestic unmanned aerial vehicle (UAV) production base.
Iran filled that gap decisively.
Beginning in 2022, Iran transferred hundreds, and eventually thousands, of Shahed-series loitering munitions to Russia. These systems, particularly the Shahed-136, became a central component of Russia’s strike architecture, used extensively against Ukrainian infrastructure and urban centers.
The impact was immediate and sustained:
Iranian-designed drones were used in repeated mass attacks on Ukrainian cities, including Kyiv, causing civilian casualties and infrastructure damage
Russia transitioned from import dependency to licensed domestic production, building facilities such as the Alabuga plant to assemble Iranian-designed drones at scale
Iranian technicians and training pipelines supported integration into Russian command structures, accelerating operational effectiveness
This was not a one-time transfer. It became a persistent supply relationship, evolving into co-production and technological integration.
Assessment: Iran did not merely supply drones. It enabled Russia to industrialize low-cost, high-volume strike capability, fundamentally altering the tempo and economics of the war.
OPERATIONAL EFFECTS: CHANGING THE CHARACTER OF WAR
Iranian drones allowed Russia to adopt a new operational model:
Saturation attacks: overwhelming Ukrainian air defenses with large volumes of inexpensive systems
Cost asymmetry: forcing Ukraine to expend high-cost interceptors against low-cost drones
Persistent pressure: enabling continuous strikes on energy infrastructure
This shifted the war from episodic missile strikes to continuous attritional bombardment, especially targeting power grids and civilian infrastructure.
The result is a war increasingly defined by:
Industrial endurance
Supply chain resilience
Cost imposition strategies
Iran’s contribution sits at the center of that transformation.
FINANCIAL LIFELINE: THE GHOST FLEET AND SANCTION EVASION
Parallel to the drone war is a second, equally critical axis of cooperation: energy and financial sustainment.
Sanctions were designed to cripple Russia’s ability to fund the war. Instead, Russia adapted, drawing on methods pioneered by Iran.
At the core of this adaptation is the “shadow fleet” or “ghost fleet” system.
This system consists of:
Hundreds to over a thousand aging oil tankers operating under false flags
Shell companies masking ownership across jurisdictions
Ship-to-ship transfers to obscure oil origin
Disabled or spoofed tracking systems (AIS manipulation)
Iran has long operated a similar system to evade sanctions, moving millions of barrels of oil daily through covert networks. Russia effectively scaled and adapted this model after 2022.
By 2026:
Ukrainian intelligence identified at least 66 vessels linked to a Russia-Iran-Venezuela shadow network moving sanctioned oil
The global shadow fleet is estimated in the hundreds to over 1,000 vessels, enabling continued export flows despite Western restrictions
Recent enforcement actions underscore the scale of the system. European naval forces have begun intercepting suspected shadow fleet vessels operating under fraudulent registries, highlighting the growing international effort to disrupt this network.
THE STRATEGIC EXCHANGE: DRONES FOR CASH, CASH FOR WAR
This relationship has become a two-way strategic exchange:
Iran provides:
Drones and UAV technology
Training and industrial support
Sanctions evasion expertise
Russia provides:
Hard currency flows through energy exports
Expanded market access for sanctioned oil
Intelligence cooperation and military technology exchange
The financial dimension is decisive.
Oil revenue remains the backbone of Russia’s war economy. Even under sanctions, Moscow has continued exporting large volumes of oil, often at discounted rates but in sufficient volume to sustain military operations. Recent reporting indicates Russia generated billions in additional revenue during periods of global energy disruption, reinforcing its ability to fund the war.
Assessment: Iran’s contribution is not limited to weapons. It has helped Russia build a sanctions-resistant war economy.
Convergence of Two Sanctioned Systems
What is emerging is not a transactional relationship, but a systemic convergence:
Iran exports asymmetric warfare capability
Russia exports energy and financial resilience
Both share techniques for evading Western pressure
This convergence produces three strategic effects:
1) Sanctions Degradation
Sanctions no longer function as decisive tools. Both states have adapted faster than enforcement mechanisms.
2) War Sustainability
Russia’s ability to continue fighting is directly tied to:
Iranian drone supply
Oil revenue protected by shadow networks
3) Global Spillover Risk
The same networks:
Move weapons
Move oil
Move money
This creates a global gray-zone logistics architecture that can be redirected to other conflicts, including the Red Sea.
Implications for the Red Sea and Beyond
The connection between Ukraine and the Red Sea is not theoretical.
It is operational:
The same Iranian networks supplying Russia also support proxy forces
The same sanctions evasion systems sustain both economies
The same maritime deception tactics are used globally
This means:
Disrupting Houthi capabilities requires disrupting Iranian logistics
Disrupting Iranian logistics requires targeting global shadow networks
Targeting those networks directly impacts Russia’s war financing
Assessment
Iran’s support to Russia in Ukraine represents one of the most consequential military-industrial partnerships of the modern era.
It has:
Extended the war
Increased its lethality
Undermined sanctions as a strategic tool
At the same time, Russia’s adaptation of Iran’s shadow oil system has ensured:
Continued revenue flow
Strategic endurance
Economic resilience under pressure
This is not a temporary alignment.
It is a durable wartime ecosystem built on:
Asymmetric warfare
Sanctions evasion
Strategic necessity
Any serious effort to degrade either Russia’s war effort or Iran’s proxy network must address both sides of this system simultaneously.
Otherwise, both wars will continue to feed each other.
STRATEGIC WARNING
The United States now faces overlapping challenges.
In the Middle East:
- Iran’s proxy network
- Maritime security risks
- Alliance management under stress
IN THE INDO PACIFIC:
- Rising tensions with China
- Potential conflict over Taiwan
These theaters are interconnected through resource constraints.
The defense industrial base is finite. Munitions, naval assets, and intelligence resources must be allocated across multiple potential conflicts. Iran’s strategy implicitly exploits this constraint by forcing distributed engagement.
PRICE OF GAS AT THE PUMP
In response to the near-closure of the Strait of Hormuz - through which roughly 20% of the world’s oil flows—President Donald Trump authorized a temporary lifting of sanctions on both Iranian and Russian oil already at sea to stabilize global energy markets and prevent a price shock.
As oil prices surged above $100 per barrel due to disrupted supply, the policy allowed sanctioned crude—previously stranded on tankers—to be sold into global markets, increasing supply and reducing economic pressure. This move reflects a pragmatic wartime adjustment: prioritizing global energy stability and economic containment over strict sanctions enforcement, even though it directly provide revenue to both adversaries.
The jury is still out on whether this is a short term fix, or a meaningless “drop in the bucket” to solve a global, strategic problem.
CONCLUSION
This conflict did not emerge overnight.
It was built - decision by decision, decade by decade for fifty years.
Each administration addressed immediate threats. None fundamentally resolved the underlying drivers of instability.
The result is a system that sustains itself in a perpetual loop.
The final question is not how we got here.
It is whether the United States can recognize the system it helped create - and adapt fast enough to prevent it from expanding beyond its control, from a major regional conflict - to the beginnings of a World War.
Iran has earned the attention it is currently getting: Long overdue.
Thousands of dead Americans - over a continuous fifty years on an “undeclared war.”
https://www.linkedin.com/posts/roman-sheremeta-14972a50_while-the-us-is-lifting-sanctions-on-russia-ugcPost-7441847139132915713-Ln4z?utm_source=share&utm_medium=member_desktop&rcm=ACoAAAXnUrIB7ijcycJnXNAuUGUR1ktO5EFW-9E
Wow! What a breath of fresh air! Great article, but you didn’t mention the importance of the petrodollar system in all this. It basically underpins the US economy and is a main driver of US Middle East policy.
Keep up the great work!!