Havana Crossroads
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Havana Crossroads

By Simvado

Step into the tense world of Cold War diplomacy in 1960s Havana. As a diplomatic envoy caught between superpowers, every conversation is a potential intelligence asset and every misstep could escalate to nuclear confrontation.

CategoryDiplomacy
Difficultyexecutive
Duration95 min
Modules4
FormatBranching Narrative

Environment Gallery

Havana Crossroads environment 1
Havana Crossroads environment 2
Havana Crossroads environment 3

Scenario Overview

Havana, 1962. The Cuban Revolution is three years old, and the island has become the most dangerous flashpoint in the Cold War. Soviet military advisors are arriving in increasing numbers. The CIA is running covert operations from safe houses in Vedado. And the diplomatic community — what remains of it — operates in a twilight zone where every cocktail party is an intelligence-gathering operation and every handshake could be a trap.

You have been sent to Havana under diplomatic cover as a cultural attaché to the Swiss embassy — a neutral position that grants you access to all sides. Your true mission, known only to a handful of officials in Washington, is to establish a back-channel communication line with a senior figure in the Cuban government who has signaled, through intermediaries, a willingness to discuss de-escalation. If this channel can be established and maintained, it could prevent the looming crisis that intelligence analysts fear is only weeks away.

But Havana is a city of mirrors. The KGB is watching the Americans. The Americans are watching the Cubans. The Cubans are watching everyone. Your Swiss cover gives you room to maneuver, but it also makes you a target of opportunity for every intelligence service operating on the island. One wrong meeting, one intercepted communication, one moment of misplaced trust, and you could trigger the very escalation you were sent to prevent. The tropical heat is oppressive, the mojitos are excellent, and the stakes could not possibly be higher.

Skills Developed

diplomacyintelligencehistorical analysisdecision making

Learning Objectives

  • 1Operate effectively in a contested diplomatic environment where allies and adversaries are not clearly distinguished
  • 2Gather and assess intelligence through interpersonal interactions while maintaining diplomatic cover
  • 3Navigate the ethical complexities of conducting secret negotiations outside official governmental channels
  • 4Analyze historical geopolitical dynamics and apply lessons to real-time decision-making under Cold War constraints
  • 5Manage personal risk and operational security in a hostile intelligence environment

Scoring Dimensions

Every decision you make is scored across five leadership dimensions.

📊

Financial Impact

🛡️

Reputational Risk

⚖️

Ethical Integrity

🤝

Stakeholder Confidence

📈

Long-term Stability

Modules (4)

01

Arrival & Assessment

Free Demounreal

20 min

You arrive in Havana with official cover. Assess the political landscape, identify key players, and establish your operating environment.

02

Embassy Operations

unreal

25 min

Navigate the complex web of embassy politics, local contacts, and competing intelligence agencies. Trust is your most valuable and dangerous currency.

03

Secret Negotiations

unreal

25 min

A secret back-channel opens. The stakes couldn’t be higher — you’re negotiating outside official channels with potential consequences for global peace.

04

The Resolution

unreal

25 min

Events are accelerating beyond anyone’s control. Make your final move — the outcome could prevent or trigger the next global crisis.

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