Repeating the Same Strategic Mistakes in the Middle East: A Warning from History
Summary
Fourteen days into a joint American-Israeli air campaign against Iran, strategic analyst Steven Simon warns that despite devastating military gains — including the death of Supreme Leader Khamenei and the destruction of 90% of Iran's missile stockpiles — the United States risks repeating the historical mistake of winning a war militarily while failing to achieve lasting political resolution. Drawing on defense strategist Fred Iklé's principle that governments are skilled at starting wars but dangerously poor at ending them, Simon argues that a severely weakened Iran under the newly appointed and illegitimate Mojtaba Khamenei will likely survive through Revolutionary Guard support and nationalist defiance, mirroring how the Islamic Republic endured after its humiliating 1988 ceasefire. Even in its degraded state, Iran retains meaningful asymmetric capabilities — including mines, fast-attack boats, and proxy networks — that could threaten global energy markets and the critical Strait of Hormuz, through which roughly 20% of the world's oil passes. Most dangerously, a humiliated Iranian regime that watched its supreme leader killed by Israeli and American action will be more motivated than ever to covertly rebuild a nuclear deterrent, meaning the strikes may have bought years but not permanent security. Simon concludes that without a deliberate post-war political framework built into the conflict's conduct from the outset — rather than improvised afterward — the current campaign risks producing the same cycle of Iranian revanchism and regional instability that previous confrontations have generated.
Key Takeaways
- 1. Despite appearing militarily successful, the U.S.-Israeli campaign lacks a coherent war termination strategy, which historically transforms apparent victories into unresolved, prolonged conflicts
- 2. Iran's new supreme leader, Mojtaba Khamenei, lacks clerical legitimacy and popular support, making him entirely dependent on the Revolutionary Guards and nationalist defiance rhetoric — virtually guaranteeing Iranian persistence rather than collapse
- 3. A weakened Iran still poses significant asymmetric threats to global energy markets, particularly the Strait of Hormuz, using low-cost tools like mines and fast-attack boats that are difficult to deter through airstrikes alone
- 4. The destruction of Iran's nuclear infrastructure will likely accelerate covert nuclear weapons development, as Iranian leaders will view a nuclear deterrent as the only guarantee against future strikes of this magnitude
- 5. Historical precedent — from post-WWII Germany and Japan to Khomeini's 1988 ceasefire — demonstrates that durable peace requires meticulous post-conflict political planning, something conspicuously absent from the Trump administration's current approach