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:

  1. Special Waiver Issued: Trump administration granted Dmitriev entry despite sanctions barring American citizens from dealing with him
  2. 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
  3. 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:

  1. 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
  2. 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
  3. 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
  4. 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:

  1. No NATO Membership: Ukraine pledges never to join NATO
    • Duration: Permanent prohibition
    • Context: NATO membership was Ukraine’s constitutional goal
  2. 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?
  3. 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
  4. 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:

  1. 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)?
  2. 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?
  3. 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:

  1. No automaticity: NATO Article 5 is automatic; this requires political decision
  2. No forward presence: No troops in Ukraine itself
  3. Economic focus: Primary deterrent appears to be sanctions, not military force
  4. 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)

  1. Language Policy: Russian becomes official language nationwide in Ukraine
    • Impact: Reverses Ukraine’s de-Russification policies
    • Symbol: Cultural subordination to Russia
  2. 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
  3. 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
  4. 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
  5. 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
  6. 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:

  1. 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
  2. G8 Return: Russia readmitted to what becomes G8 again
    • Symbol: Full rehabilitation on world stage
    • History: Russia expelled in 2014 after Crimea annexation
  3. Frozen Assets: Russia regains access to $100+ billion in frozen Central Bank reserves
    • Use: Ostensibly for reconstruction; no guarantee Russia contributes to Ukraine
  4. 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:

  1. EU Membership Eligibility: Ukraine remains eligible (but no timeline or guarantee)
  2. Reconstruction Fund: Creation of Ukraine Development Fund for:
    • Technology investment
    • Data centers
    • Artificial intelligence
    • Source: Unspecified; likely Western nations, not Russia
  3. Gas Infrastructure: U.S.-Ukraine cooperation to rebuild pipelines and storage
    • Problem: Requires sharing with Russia per Point 15
  4. 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)

  1. 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
  2. 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?
  3. 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:

  1. Personality-dependent: Relies on Trump personally, creating uncertainty beyond his presidency
  2. No military enforcement: Peace Council can only impose sanctions
  3. Sequential risk: Ceasefire timing allows for exploitation
  4. 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:

  1. Ultimatum: Accept by Thanksgiving or face consequences
  2. Aid Threat: Warning of reduced military and intelligence assistance
  3. False Choice: “Lose dignity or lose key partner” framing
  4. Time Pressure: One-week deadline for complex geopolitical decision
  5. Isolation: Presented without European input initially
  6. Battlefield Reality: Russia making territorial gains as pressure tactic

Toward Europe:

  1. Fait Accompli: Presented with plan already drafted
  2. Split Strategy: Initially excluded European allies
  3. Transatlantic Rift: Forced to choose between supporting U.S. or Ukraine
  4. 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:

  1. Only ASEAN member to impose sanctions on Russia
  2. Co-sponsored UN resolutions against Russia (only ASEAN state)
  3. Banned transactions with VTB, VEB.RF, Promsvyazbank, Bank Rossiya
  4. Export controls on military goods, electronics, computers to Russia
  5. Provided humanitarian aid to Ukraine (three tranches)
  6. 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