EXECUTIVE SUMMARY
In late October 2025, Trump administration officials including special envoy Steve Witkoff, son-in-law Jared Kushner, and sanctioned Russian envoy Kirill Dmitriev met secretly in Miami to draft a 28-point peace plan to end the Russia-Ukraine war. The plan, presented to Ukraine with a Thanksgiving deadline, represents one of the most consequential—and controversial—diplomatic initiatives since the war began in February 2022.
Key Characteristics:
- Drafted outside normal diplomatic channels with direct Russian involvement
- Demands major Ukrainian territorial and military concessions
- Offers ambiguous security guarantees
- Pressures Ukraine with threats to withdraw military support
- Fundamentally challenges the post-WWII international order
CASE STUDY ANALYSIS
Background Context
Current Military Situation (November 2025)
Ukrainian Position:
- Russia controls approximately 19% of Ukrainian territory (equivalent to U.S. state of Ohio)
- Since January 2025, Russia has averaged 168 square miles of territorial gains per month
- In September-October 2025, Russia gained 154 square miles
- Critical cities like Pokrovsk are under severe pressure, encircled on three sides
- Ukraine holds only 14.5% of the Donbas region it once controlled
Russian Advantages:
- Produces approximately 35,000 Shahed drones annually (expected to reach 40,000 by 2030)
- Conducted first 500-drone raid in 2025
- Successfully destroyed 60% of Ukraine’s gas production ahead of winter 2025-2026
- Maintains superior numbers and resources despite heavy casualties (790,000+ killed or injured vs Ukraine’s 400,000+)
Ukrainian Resilience:
- Developed robust deep-strike capability against Russian refineries (reduced capacity by 10-38%)
- Domestically produced Flamingo missiles with 3,000km range
- Successfully struck Russian military facilities deep inside Russia
- Maintained defensive lines despite overwhelming pressure
The Genesis: Miami Meeting (Late October 2025)
Participants:
- Steve Witkoff – Trump’s special envoy (lead negotiator)
- Jared Kushner – Trump’s son-in-law
- Kirill Dmitriev – Head of Russian Direct Investment Fund (RDIF), sanctioned by U.S. since 2022, close Putin ally
Process Irregularities:
- Special Waiver Issued: Trump administration granted Dmitriev entry despite sanctions barring American citizens from dealing with him
- Key Officials Excluded:
- Secretary of State Marco Rubio claims he was briefed, but multiple U.S. officials disputed this
- Special Envoy Keith Kellogg (stepping down January 2026) completely cut out
- Senior State Department and NSC officials not consulted
- Venue Selection: Meeting held at Faena Hotel in Miami, owned by Access Industries (run by Russian billionaire Len Blavatnik, who partnered with sanctioned oligarch Viktor Vekselberg)
Historical Context – Dmitriev’s Track Record:
- During first Trump administration, met with Erik Prince (Blackwater founder) to discuss U.S.-Russia relations
- Drafted reconciliation plan with Kushner’s friend to strengthen U.S.-Russia ties
- Coordinated ventilator delivery to U.S. during pandemic, causing Treasury Department concerns about sanctions violations
- Appeared at World Economic Forum in Davos promoting U.S.-Russia trade ties
The 28-Point Plan: Detailed Analysis
TERRITORIAL PROVISIONS (Points 1-4)
Ukrainian Concessions:
- Crimea Recognition: Crimea, Luhansk, and Donetsk recognized as “de facto Russian, including by the United States”
- Impact: Legitimizes 2014 annexation and 2022 invasion gains
- Precedent: First time post-WWII that U.S. officially recognizes territorial conquest
- Withdrawal from Donetsk: Ukraine must withdraw from parts of Donetsk it currently controls
- Impact: Russia gains territory it failed to capture militarily
- Creates: Demilitarized buffer zone internationally recognized as Russian Federation territory
- Frozen Battle Lines: Kherson and Zaporizhzhia frozen along current contact lines
- Impact: Russia keeps 75% of Zaporizhzhia, 72% of Kherson
- Reality: Russia controls less than it claims; plan gives them claim to more
- Relinquishment Clause: Russia to “relinquish other agreed territories it controls outside the five regions”
- Ambiguity: Which territories? Who decides? No enforcement mechanism specified
Strategic Assessment: This territorial settlement gives Russia:
- More than it holds: Territory in Donetsk Ukraine still controls
- Strategic depth: Control of land bridge to Crimea
- Economic assets: Industrial Donbas region, Black Sea access
- Political victory: International recognition of gains from illegal invasion
MILITARY CONSTRAINTS (Points 5-7)
Ukrainian Limitations:
- No NATO Membership: Ukraine pledges never to join NATO
- Duration: Permanent prohibition
- Context: NATO membership was Ukraine’s constitutional goal
- Military Size Caps: Specific limits on Ukrainian armed forces size (reportedly 600,000 troops)
- Comparison: Russia maintains military superiority
- Problem: How to enforce against future Russian aggression?
- Long-Range Weapons Ban: Restrictions on possession of long-range missiles
- Impact: Eliminates Ukraine’s ability to strike Russian territory
- Asymmetry: Russia faces no such restrictions
- Nuclear Status: Ukraine must remain non-nuclear state
- Historical irony: Ukraine gave up nuclear weapons in 1994 Budapest Memorandum in exchange for security guarantees Russia later violated
Russian Military Freedom:
- No size restrictions on Russian military
- No weapons limitations
- Retains nuclear arsenal
- Can position forces at Ukraine’s border
Strategic Assessment: These provisions create permanent Ukrainian military inferiority while Russia maintains offensive capability. Ukraine becomes essentially defenseless without robust external security guarantees—which the plan provides only ambiguously.
SECURITY GUARANTEES (Points 8-10)
The “Article 5 Lite” Promise:
- Trigger: If Russia attacks Ukraine after the agreement
- Response promised: “Decisive coordinated military response”
- Critical ambiguities:
- Who provides the military response?
- What constitutes “decisive”?
- Is U.S. military intervention guaranteed?
- What about non-conventional attacks (cyberwarfare, hybrid warfare)?
- Enforcement Mechanism: “All global sanctions will be reinstated”
- Problem: Sanctions didn’t stop Russia in 2014 or 2022
- Question: Will economic measures deter future aggression?
- Security Guarantee Termination: Guarantee void if Ukraine attacks Moscow or St. Petersburg “without cause”
- Ambiguity: Who determines “without cause”?
- Asymmetry: Russia can attack any Ukrainian city without voiding the agreement
European Component:
- European fighter jets stationed in Poland (not Ukraine)
- Unclear what “European” means (EU? Individual countries?)
- “Fighter jets” is militarily imprecise terminology
- Distance from Poland reduces deterrent effect
Strategic Assessment: The security guarantee is fundamentally weaker than NATO Article 5 because:
- No automaticity: NATO Article 5 is automatic; this requires political decision
- No forward presence: No troops in Ukraine itself
- Economic focus: Primary deterrent appears to be sanctions, not military force
- Exploitable loopholes: Terminates if Ukraine defends itself against Moscow
Expert Analysis: Dara Massicot (Carnegie Endowment): “Security guarantees based primarily on economic sanctions rather than robust military commitments are unlikely to deter future aggression.”
POLITICAL & SOCIAL PROVISIONS (Points 11-18)
- Language Policy: Russian becomes official language nationwide in Ukraine
- Impact: Reverses Ukraine’s de-Russification policies
- Symbol: Cultural subordination to Russia
- Media Freedom: Abolish “discriminatory measures” against Russian media and education
- Concern: Opens door for Russian propaganda operations
- History: Russian media used to justify 2014 and 2022 invasions
- Nazi Ideology Ban: “All Nazi ideology and activities must be rejected and prohibited”
- Context: Echoes Russian propaganda justification for invasion
- Problem: Russia has used “de-Nazification” as pretext for war crimes
- Zaporizhzhia Nuclear Plant: Energy shared 50-50 between Ukraine and Russia
- Issue: Legitimizes Russian occupation of Europe’s largest nuclear facility
- Safety: International Atomic Energy Agency repeatedly warned about safety risks under Russian control
- Elections: Ukraine must hold elections within 100 days
- Challenge: How to conduct free elections with territory occupied and millions displaced?
- Timing: Benefits Russia by creating internal Ukrainian political instability
- Amnesty: All parties receive amnesty for actions during the war
- Implication: No war crimes prosecutions for Russian officials or soldiers
- Precedent: Contradicts international justice norms
Strategic Assessment: These provisions systematically undermine Ukrainian sovereignty and national identity while providing Russia with:
- Cultural influence through language and media
- Control over critical infrastructure
- Immunity from accountability
- Tools to destabilize Ukrainian democracy
ECONOMIC PROVISIONS (Points 19-25)
For Russia:
- Sanctions Relief: “Global sanctions will be lifted in line with Russia demonstrating compliance”
- Timeline: Immediate upon agreement
- Value: Hundreds of billions in frozen assets and trade
- G8 Return: Russia readmitted to what becomes G8 again
- Symbol: Full rehabilitation on world stage
- History: Russia expelled in 2014 after Crimea annexation
- Frozen Assets: Russia regains access to $100+ billion in frozen Central Bank reserves
- Use: Ostensibly for reconstruction; no guarantee Russia contributes to Ukraine
- Economic Cooperation: Long-term U.S.-Russia cooperation in:
- Artificial Intelligence
- Energy sector
- Rare earth minerals mining
- Impact: Rewards Russia economically for military aggression
For Ukraine:
- EU Membership Eligibility: Ukraine remains eligible (but no timeline or guarantee)
- Reconstruction Fund: Creation of Ukraine Development Fund for:
- Technology investment
- Data centers
- Artificial intelligence
- Source: Unspecified; likely Western nations, not Russia
- Gas Infrastructure: U.S.-Ukraine cooperation to rebuild pipelines and storage
- Problem: Requires sharing with Russia per Point 15
- Reparations: None specified or required from Russia
Strategic Assessment: The economic provisions heavily favor Russia:
- Immediate benefits: Sanctions relief, frozen assets, G8 return
- No costs: No requirement to pay reparations for massive destruction
- Future opportunities: Economic partnerships with U.S. in strategic sectors
Meanwhile, Ukraine receives:
- Uncertain benefits: Reconstruction depends on Western funding
- Conditional gains: EU membership remains aspirational
- Shared resources: Must split energy infrastructure with occupier
ENFORCEMENT & IMPLEMENTATION (Points 26-28)
- Peace Council: Headed by President Donald J. Trump personally
- Structure: Trump chairs the monitoring body
- Duration: Unclear what happens after Trump’s presidency
- Authority: Can impose sanctions for violations
- Precedent: Modeled on Gaza ceasefire oversight
- Legal Binding: Agreement described as “legally binding”
- Question: Under what legal framework? International Court of Justice? Arbitration?
- Enforcement: Who enforces if Trump Peace Council fails?
- Ceasefire Mechanism: Takes effect “immediately after both sides retreat to agreed points”
- Risk: Ukraine retreats first, Russia delays or refuses
- Verification: Who monitors compliance in real-time?
Strategic Assessment: Enforcement mechanisms are dangerously weak:
- Personality-dependent: Relies on Trump personally, creating uncertainty beyond his presidency
- No military enforcement: Peace Council can only impose sanctions
- Sequential risk: Ceasefire timing allows for exploitation
- Limited duration: Trump’s presidency ends January 2029; what then?
Process Analysis: How the Deal Was Made
Timeline of Events
Late October 2025: Miami meeting produces 28-point draft
Early November 2025: Rustem Umerov (Ukraine’s Defense Council Secretary) meets Witkoff in Miami
- Umerov claims “technical” role only
- Denies discussing plan substance
November 20, 2025: U.S. gives plan to Ukraine via Turkish government
November 21, 2025: Plan directly presented in Kyiv
- U.S. Army Secretary Daniel Driscoll leads delegation
- Zelenskyy responds: “We will work on it”
November 22, 2025 (Friday):
- Trump sets Thanksgiving (November 27) deadline
- Reuters reports U.S. warns of military aid reduction if Ukraine refuses
- European leaders convene emergency G20 meeting
- Putin calls plan “basis” for agreement (signaling Russia wants more concessions)
November 23, 2025 (Saturday):
- Western allies issue joint statement: plan “requires additional work”
- Geneva meeting scheduled for November 24 (Sunday) with national security advisers from France, Britain, Germany, EU, U.S., and Ukraine
Pressure Tactics Employed
Against Ukraine:
- Ultimatum: Accept by Thanksgiving or face consequences
- Aid Threat: Warning of reduced military and intelligence assistance
- False Choice: “Lose dignity or lose key partner” framing
- Time Pressure: One-week deadline for complex geopolitical decision
- Isolation: Presented without European input initially
- Battlefield Reality: Russia making territorial gains as pressure tactic
Toward Europe:
- Fait Accompli: Presented with plan already drafted
- Split Strategy: Initially excluded European allies
- Transatlantic Rift: Forced to choose between supporting U.S. or Ukraine
- Economic Lever: Implicit threat that U.S. might cut Ukraine funding unilaterally
Reaction Analysis
Ukraine’s Position:
- Zelenskyy publicly stated red lines:
- No recognition of Ukrainian territory as Russian
- No limits on armed forces size
- “Dignified peace” that respects sovereignty
- Privately negotiating through “technical” channels
- Seeking European support before committing
European Response:
- Finland’s President Stubb: “Matters concerning Ukraine are for Ukraine to decide”
- Joint statement (EU, Germany, France, UK, Canada, Netherlands, Spain, Finland, Italy, Japan, Norway):
- Concerned about military limitations leaving Ukraine vulnerable
- EU/NATO decisions require member consent
- Plan needs “additional work”
- Emergency meetings at G20, follow-up in Geneva
- Walking tightrope: can’t fully oppose U.S., can’t abandon Ukraine
Russian Response:
- Putin: Plan is “basis” for agreement
- Kremlin signal: Russia wants additional concessions beyond 28 points
- Dmitriev optimistic about U.S. approach
- Moscow’s leverage growing with battlefield successes
Congressional Response (U.S.):
- Senator Roger Wicker (Republican, Armed Services Committee Chairman): “Highly skeptical it will achieve peace”
- Criticism of forcing Ukraine to cede land to “war criminal Putin”
- Bipartisan concern about process and Dmitriev involvement
Singapore’s Dilemma: Case Study in Small State Vulnerability
Singapore’s Principled Stance (2022-2025)
Actions Taken:
- Only ASEAN member to impose sanctions on Russia
- Co-sponsored UN resolutions against Russia (only ASEAN state)
- Banned transactions with VTB, VEB.RF, Promsvyazbank, Bank Rossiya
- Export controls on military goods, electronics, computers to Russia
- Provided humanitarian aid to Ukraine (three tranches)
- Hosted discussions at Shangri-La Dialogue 2023
Stated Rationale: Singapore’s Ambassador to UN (February 2025): “For small states like Singapore, upholding international law and the UN Charter is a matter of existential importance.”
Home Affairs Minister K. Shanmugam (March 2023): “If these principles are accepted, there is nothing to say another country cannot use the same reasoning with Singapore” – citing Dr. Mahathir’s 2022 statement about Singapore and Riau Islands being “Tanah Melayu.”
Public Support:
- 52% of Singaporeans supported sanctions on Russia (highest in ASEAN)
- 56% said paying more for fuel because of sanctions was worthwhile
- 41% supported sanctions despite economic impact
The Impossible Choice
Singapore now faces three bad options:
OPTION 1: OPPOSE THE PLAN PUBLICLY
Advantages:
- Maintains principled consistency
- Upholds international law rhetoric
- Sets example for other small states
- Preserves long-term credibility
Disadvantages:
- Risks Trump administration relationship
- Isolated opposition likely ineffective
- Potential economic/security retaliation
- May be seen as choosing Europe over U.S. in great power competition
Likelihood: LOW – Too costly, too little impact
OPTION 2: ACCEPT THE PLAN PRAGMATICALLY
Advantages:
- Maintains U.S. relationship at crucial time
- Avoids being outlier in region (ASEAN generally neutral)
- Preserves access to U.S. security umbrella
- Realistic acceptance of geopolitical facts
Disadvantages:
- Contradicts three years of stated principles
- Undermines Singapore’s moral authority
- Sets precedent that principles yield to power
- Signals to regional powers (China) that international law doesn’t matter
- Domestic credibility loss after public stood behind sanctions
Likelihood: MEDIUM – Pragmatic but painful
OPTION 3: WORK WITHIN THE FRAMEWORK
Strategy:
- Publicly express concerns about specific provisions
- Work through Geneva process to strengthen security guarantees
- Advocate for better enforcement mechanisms
- Join other small states in Forum of Small States to propose modifications
- Coordinate with European allies on improvements
- Accept final plan while making clear Singapore’s reservations
Advantages:
- Balances principles with pragmatism
- Maintains relationships with all parties
- Provides “on record” opposition for future reference
- Allows Singapore to say it tried to improve terms
- Preserves some principled stance
Disadvantages:
- May be seen as weak compromise
- Limited influence on final outcome
- Still associated with plan Singapore opposed
- Doesn’t address fundamental precedent problem
Likelihood: HIGH – Most realistic approach
Broader Implications for Singapore
Security Architecture:
- If U.S. security guarantees to Ukraine prove hollow, what about U.S. commitments to Singapore?
- Does this signal U.S. prioritizes bilateral deals with adversaries over alliance commitments?
- Will Singapore need to recalibrate defense planning assumptions?
Regional Dynamics:
- China observing closely: Does military might + negotiated settlement = success?
- Taiwan implications: Similar formula possible for “reunification”?
- South China Sea: Will historical claims + military presence = legitimacy?
- ASEAN unity: Further exposed as unable to respond collectively to principles violations
Economic Considerations:
- If Russia-U.S. economic cooperation proceeds, sanctions regime erodes
- Singapore’s financial sector: Caught between U.S. sanctions policy and Russia normalization
- Trade disruption: Uncertain how reconstruction funds flow, opportunities vs. risks
Institutional Credibility:
- UN Charter and international law shown as aspirational, not binding
- Forum of Small States loses leverage if great powers ignore them
- Multilateral institutions (UN, ICC) further weakened
STRATEGIC OUTLOOK: THREE SCENARIOS
SCENARIO 1: PLAN SUCCEEDS – “PAX TRUMPIANA” (30% Probability)
How It Unfolds
Phase 1: Reluctant Acceptance (December 2025 – February 2026)
Geneva negotiations produce minor modifications:
- Enhanced monitoring provisions for ceasefire
- Slightly stronger language on security guarantees
- Clearer timeline for sanctions relief tied to Russian compliance
- European military presence in Poland formalized
Ukraine accepts modified plan under extreme pressure:
- U.S. threatens immediate aid cutoff
- Battlefield situation deteriorates further (Russia takes Pokrovsk)
- Zelenskyy calculates that continuing the war means losing more territory
- European allies reluctantly support as “best available option”
Russia accepts because plan gives them more than they hold militarily:
- Territorial gains beyond current control
- Sanctions relief and economic reintegration
- No reparations requirements
- International recognition of Crimea annexation
Phase 2: Implementation (March – December 2026)
Ceasefire holds initially:
- Both sides exhausted from years of war
- International monitors (Trump Peace Council) deployed
- Demilitarized zones established
- POW exchanges completed
Ukraine begins implementing concessions:
- Military reduction to agreed levels (painful but completed)
- Territorial withdrawals from Donetsk positions
- Russian language and media access expanded
- Elections held (Zelenskyy possibly loses to peace candidate)
Russia receives benefits:
- Sanctions lifted progressively
- Frozen assets released ($100B+)
- Readmitted to G8
- Begins economic cooperation with U.S. in AI, energy, rare earth minerals
Medium-Term Dynamics (2027-2030)
Ukraine’s Trajectory:
- Massive reconstruction begins with Western funding
- Economy slowly recovers but remains smaller than pre-war
- Political instability as nation processes loss
- Brain drain continues as educated Ukrainians emigrate
- Military remains capped, focused on defense of remaining territory
- Moves toward EU membership but process lengthy
- National identity crisis: How to reconcile loss with dignity?
Russia’s Trajectory:
- Economic recovery from sanctions relief
- Putin claims historic victory: reunified “Russian lands”
- Increased repression domestically to prevent questioning of war costs
- Reintegrates into global economy but with suspicious partners
- Continues military modernization without constraints
- Relationship with China remains close but competitive
- Tests boundaries of peace agreement with small violations
U.S. Position:
- Trump claims major foreign policy victory
- Uses Ukraine deal to pressure China on Taiwan
- Increases focus on Indo-Pacific (away from Europe)
- Transatlantic relationship strained but functional
- Domestic debate: Did we betray Ukraine or end unnecessary war?
European Response:
- Massive defense spending increase
- Accelerates “strategic autonomy” from U.S.
- Closer defense integration (European army concepts revived)
- Finland, Baltics, Poland massively fortify eastern borders
- Ukraine reconstruction becomes European project
- Germany completes military transformation ahead of schedule
Long-Term Stability (2030-2040)
Best Case – “Cold Peace”:
- Ceasefire holds for decade+
- Ukraine prospers economically despite territorial losses
- Russia gradually democratizes after Putin (leadership change 2033-2035)
- New Russian government reconciles with Ukraine
- Eventually territorial disputes resolved peacefully
- NATO-Russia relationship normalizes
- International law regime slowly recovers
Realistic Case – “Frozen Conflict 2.0”:
- Ceasefire holds but no real peace
- Regular small-scale violations along demarcation lines
- Russia continues hybrid warfare (cyber, propaganda) below agreement threshold
- Ukraine remains in permanent security limbo
- Periodic crises require Trump Peace Council interventions
- New generation of Ukrainians grows up seeking revenge
- Conflict reignites in 2035-2040 when conditions change
Worst Case – “Interwar Period”:
- Ceasefire is just pause for Russia to rebuild
- By 2032-2035, Russia invades again to take remainder of Ukraine
- Security guarantees prove hollow (U.S. unwilling to fight)
- Europe lacks capability to defend Ukraine alone
- Russia achieves full subjugation of Ukraine
- Precedent encourages Chinese aggression against Taiwan
- Returns to pre-WWII great power imperialism
Singapore’s Position in This Scenario
Immediate Impact (2026-2028):
- Quietly accepts the plan while maintaining reservations
- Focuses on strengthening deterrence with regional partners
- Increases defense spending 10-15%
- Deepens security partnerships with Japan, South Korea, Australia
- Accelerates efforts in Forum of Small States
Medium-Term Adjustments (2028-2035):
- Recalibrates U.S. security relationship assumptions
- Invests heavily in asymmetric defense capabilities
- Promotes alternative international law enforcement mechanisms
- Balances carefully between U.S. and China as both pursue transactional diplomacy
- Leads small state coalition on principles-based issues
Long-Term Implications (2035-2045): If the peace holds:
- Singapore’s pragmatic acceptance vindicated
- International system adapts to “might makes right lite” norms
- Small states develop new survival strategies
If peace fails:
- Singapore’s warnings about precedent proven correct
- But lacks alternative that would have prevented it
- International order fundamentally damaged regardless
SCENARIO 2: PLAN FAILS – “ENDLESS WAR” (50% Probability)
How It Unfolds
Phase 1: Negotiation Breakdown (December 2025 – January 2026)
Ukraine rejects plan even in modified form:
- Zelenskyy calculates accepting means eventual absorption by Russia
- Ukrainian public overwhelmingly opposes territorial concessions
- Parliament refuses to ratify any agreement ceding territory
- Military leadership warns caps would leave nation defenseless
Russia adds demands beyond the 28 points:
- Putin indicates plan is just “basis” – wants more
- Additional territorial claims in Kharkiv, Mykolaiv, Odesa
- Demands regime change in Kyiv
- Insists on complete demilitarization, not just caps
- Requirements seen as designed to be unacceptable
U.S.-Ukraine relationship severely strains:
- Trump cuts military aid by 40% in retaliation
- Intelligence sharing reduced
- U.S. signals Europe must bear full burden
- Zelenskyy appeals directly to American people over Trump’s head
Phase 2: European Pivot (February – June 2026)
Europe steps in to fill U.S. gap:
- Emergency EU Summit creates €200B Ukraine Defense Fund
- Germany, France, UK commit to long-term military support
- EU fast-tracks Ukraine membership process
- Poland, Baltics, Nordic countries provide immediate military aid
- European defense industry ramps up production
Russia interprets as weakness:
- Sees U.S.-Ukraine split as opportunity
- Launches major offensive in spring 2026
- Targets Kharkiv, intensifies pressure on Pokrovsk, Zaporizhzhia
- Calculation: Ukraine weakened without U.S. aid, Europe won’t fight
Ukraine holds but suffers:
- Loses additional territory (3-4% more)
- Casualty rates increase
- Domestic support for war remains high but economic suffering intense
- Millions more refugees flee to Europe
Medium-Term Dynamics (2026-2030)
The Grinding Stalemate:
Military situation:
- Front lines stabilize with minor fluctuations
- Neither side capable of decisive breakthrough
- War transitions to WWI-style attrition
- Constant artillery duels, drone warfare, cyber attacks
- Periodic Russian offensives gain 50-100 square miles at massive cost
Ukrainian strategy:
- Focus on defense while building capacity
- Deep strikes on Russian infrastructure continue
- Gradually receiving European F-16s, advanced systems
- Mobilization remains universal
- Economic survival dependent on European support
Russian strategy:
- Slow grinding advance continues
- Rotates forces to manage casualties
- Economy increasingly militarized
- Sanctions avoidance through China, India, Middle East
- Domestic repression intensifies to maintain war support
U.S. role diminishes:
- Trump administration (2025-2029) provides minimal support
- Relationship with Europe deteriorates over burden-sharing
- Focus shifts entirely to Indo-Pacific
- America First rhetoric intensifies
- 2028 election: Ukraine becomes partisan issue
Humanitarian Catastrophe:
- 2026-2030: Additional 3-5 million Ukrainian refugees
- Total displacement reaches 15 million+ (one-third of pre-war population)
- European integration crisis as refugee flows continue
- Russian-controlled territories: forced Russification, disappearances
- Ukraine proper: Infrastructure devastation, economic collapse
- War crimes continue with no accountability
Economic Impacts:
Ukraine:
- GDP contracts 45-50% from pre-war level
- Surviving on life support from EU
- Reconstruction impossible during active conflict
- Young population decimated by war and emigration
- Agricultural exports disrupted, food security global concern
Russia:
- Economy adapts to permanent war footing
- Living standards decline 20-30%
- Brain drain accelerates (1-2 million emigrate)
- Increasing dependence on China
- Gradual economic vassalization to Beijing
Europe:
- Annual Ukraine support costs €80-120B
- Defense spending reaches 3-4% of GDP
- Economic growth slows under burden
- Political instability as populist parties oppose costs
- Refugee integration challenges mount
Global:
- Energy markets permanently disrupted
- Food prices elevated (Ukraine/Russia = 30% global grain)
- Inflation remains higher than pre-war
- Global South countries increasingly blame “Western” war
- Multipolar fragmentation accelerates
Long-Term Trajectories (2030-2040)
Most Likely: War of Attrition Continues
2030 situation:
- Russia controls 22-25% of Ukraine
- Stalemate along 1,200km front line
- Neither side can achieve military victory
- Both populations exhausted but unwilling to concede
Paths to eventual resolution:
Option A – Leadership Change in Russia (2033-2035):
- Putin dies or is removed
- Succession crisis in Moscow
- New leadership seeks off-ramp from failing war
- Negotiations resume with more realistic terms
- Ceasefire achieved but without full resolution
- Frozen conflict status for decades
Option B – Ukrainian Military Victory (2032-2038):
- European military support enables Ukrainian counteroffensive
- Russian military finally collapses from attrition
- Ukraine retakes most occupied territory
- Russia forced into humiliating peace
- Putin’s regime destabilizes
- Risk: Nuclear escalation if Russia faces defeat
Option C – Russian Victory through European Collapse (2030-2035):
- European political will breaks under sustained costs
- Populist governments in multiple EU states
- Support for Ukraine ends
- U.S. remains disengaged
- Ukraine forced into capitulation worse than 28-point plan
- Russia achieves total victory
Option D – True Stalemate Institutionalized (2035+):
- Neither side wins
- Conflict becomes accepted reality like Cyprus, Korea
- Generations grow up with division
- Periodic flare-ups but no resolution
- Becomes permanent feature of European security landscape
Singapore’s Position in This Scenario
Immediate Impact (2026-2028):
- Vindication of principled opposition to forced settlement
- But also frustration that war continues with no resolution
- Singapore maintains support for Ukraine through humanitarian aid
- Continues sanctions on Russia despite economic cost
- Works with like-minded states to support international law
Medium-Term Challenges (2028-2035):
- U.S. disengagement from Europe signals potential disengagement from Asia
- Singapore accelerates defense modernization
- Strengthens ASEAN centrality as hedge
- Balances between U.S. (unreliable), China (threatening), Europe (distant)
- Faces domestic pressure: Why still sanctioning Russia years later?
Long-Term Strategic Environment (2035-2045):
- International order completely fractured
- Great powers pursue spheres of influence
- Small states develop survival strategies without reliable international law
- Singapore becomes leader of “nonaligned” small states coalition
- Focus on resilience, deterrence, economic strength
- Permanent state of strategic uncertainty
Existential Questions for Singapore:
- If international law can’t protect Ukraine after years of support, what protects Singapore?
- If U.S. abandons Ukraine under pressure, would it abandon Singapore?
- If Europe can’t sustain support for neighbor, who helps distant Singapore?
- Is Singapore’s model of relying on rules-based order obsolete?
SCENARIO 3: PLAN TRIGGERS ESCALATION – “EXPANDING WAR” (20% Probability)
How It Unfolds
Phase 1: Unintended Consequences (December 2025 – March 2026)
Ukraine forced to accept plan under maximum pressure:
- U.S. completely cuts military aid
- Battlefield situation collapses without support
- Zelenskyy government falls, replaced by “peace” government
- New Ukrainian leadership signs agreement to stop bleeding
- Implementation begins immediately
Russia interprets acceptance as victory and Ukrainian weakness:
- Putin sees validation of military approach
- Emboldened by success, begins