Russian gains in Ukraine will pick up in fall/winter
Russia's military advances in Ukraine will accelerate through the fall and winter of 2026-2027.
Only one outcome of one event in this book can win, so the payout is a range.
Bet timeline: 13 markets, first verdict Dec 31, 2026, last Jan 1, 2028
- Will Russia capture Kostyantynivka by...?, Dec 31, 2026 (in 4 months), still open
- Which cities will Russia enter by December 31?, Dec 31, 2026 (in 4 months), still open
- Will Russia capture Sloviansk by December 31?, Dec 31, 2026 (in 4 months), still open
- Will Russia capture Kupiansk-Vuzlovyi by...?, Dec 31, 2026 (in 4 months), still open
- Will Ukraine re-enter Myrnohrad by December 31?, Dec 31, 2026 (in 4 months), still open
- Will Ukraine recapture Crimean territory by...?, Dec 31, 2026 (in 4 months), still open
- Ukraine signs peace deal with Russia before 2027?, Dec 31, 2026 (in 4 months), still open
- Another NATO article 4 by...?, Dec 31, 2026 (in 4 months), still open
- Russia coup attempt in 2026?, Dec 31, 2026 (in 4 months), still open
- Where will Trump and Putin meet next in 2026?, Dec 31, 2026 (in 4 months), still open
- Ukraine peace referendum passed before 2027?, Dec 31, 2026 (in 4 months), still open
- Will Ukraine sign an EU accession treaty by December 31, 2027?, Jan 1, 2028 (in 16 months), still open
- Will Ukraine agree to give up the rest of Donbas before 2027?, Dec 31, 2026 (in 4 months), still open
Money back if its biggest bet lands. First verdict Dec 31, 2026.
What has to be true
Every claim this book is built on, and what has happened to it so far.
What shows up first
Pokrovsk falls under Russian control this fall95%at save
This book backs
Pokrovsk falls to Russia
What that looks like: Ukrainian General Staff confirms withdrawal from Pokrovsk
Druzkhivka +1 moreWhich cities will Russia enter by December 31?99%
Will Ukraine re-enter Myrnohrad by December 31?No92%
Markets last priced this at 95%
Kupiansk is captured or encircled by Russian forces49%at save
This book backs
Kupiansk falls to Russia
What that looks like: Russian MoD claims full control of Kupiansk
December 31Will Russia capture Kupiansk-Vuzlovyi by...?49%
Markets last priced this at 49%
Trump-Putin summit produces no binding breakthrough60%at save
This book backs
No breakthrough deal
What that looks like: Summit ends without signed agreement
Not meetWhere will Trump and Putin meet next in 2026?60%
Markets last priced this at 60%
A Russian drone or missile incursion into a NATO member (Poland, Baltics) triggers Article 4/5 consultations39%at save
This book backs
Incursion incident occurs
What that looks like: NATO invokes Article 4 consultations after airspace violation
DecemberAnother NATO article 4 by...?39%
Markets last priced this at 39%
Russian strikes on Ukraine's power grid intensify heading into winter
This book backs
Strikes on grid intensify
What that looks like: Large-scale blackouts reported across Ukrainian cities
No bet in this book covers this claim.
What confirms it
Russia captures Kostiantynivka and further Donetsk Oblast towns by winter46%at save
This book backs
Kostiantynivka falls to Russia
What that looks like: ISW reports Russian forces enter Kostiantynivka
December 31, 2026Will Russia capture Kostyantynivka by...?87%
Will Russia capture Sloviansk by December 31?Yes6%
Markets last priced this at 46%
No ceasefire or peace agreement is signed before end of winter91%at save
This book backs
No ceasefire signed
What that looks like: Peace talks collapse or remain unresolved past February
Ukraine signs peace deal with Russia before 2027?No84%
Ukraine peace referendum passed before 2027?No96%- +1 more bet
Markets last priced this at 91%
US military aid to Ukraine continues to shrink or stall under Trump administration
This book backs
US aid decreases
What that looks like: Congress or White House delays/cuts new Ukraine aid package
No bet in this book covers this claim.
European natural gas prices (TTF) rise sharply this winter amid the war
This book backs
TTF gas prices rise
What that looks like: Dutch TTF benchmark climbs above autumn levels into winter
No bet in this book covers this claim.
New EU sanctions package fails to meaningfully alter Russia's war trajectory
This book backs
Sanctions package has limited effect
What that looks like: EU sanctions package passes with carve-outs or weak enforcement
No bet in this book covers this claim.
What pays it off
Russia gains full control of Donetsk Oblast by mid-20277%at save
This book backs
Russia controls all of Donetsk
What that looks like: Russia declares full administrative control of Donetsk region
December 31, 2026Will Ukraine recapture Crimean territory by...?7%
Markets last priced this at 7%
Russia's economy proves resilient enough to sustain the offensive through 20277%at save
This book backs
Russia GDP grows
What that looks like: Russian GDP print shows continued growth despite sanctions
Russia coup attempt in 2026?Yes7%
Markets last priced this at 7%
If only some of it happens
Drag to see what a partial hit pays.
Worst case 0.7× · typically 0.9× · best case 2.8× per $1.
Pick which ones
What brings the money back
Markets priced these odds at around 14%. : around 22%.
Markets priced these landing together at around 5%. : around 31%.
Any 10 of the 13 bets landing returns the stake, whichever 10 they are. The bets named above are the fastest route, not the only one.
Where the money sits
13 bets, ranked by how much of the stake each one holds.
December 31, 2026
Will Russia capture Kostyantynivka by...?
Ukraine peace referendum passed before 2027?
Will Ukraine re-enter Myrnohrad by December 31?
Will Russia capture Sloviansk by December 31?
Ukraine signs peace deal with Russia before 2027?
Will Ukraine agree to give up the rest of Donbas before 2027?
December
Another NATO article 4 by...?
Not meet
Where will Trump and Putin meet next in 2026?
Druzkhivka +1 more
Which cities will Russia enter by December 31?
December 31
Will Russia capture Kupiansk-Vuzlovyi by...?
December 31, 2026
Russia coup attempt in 2026?
Will Ukraine sign an EU accession treaty by December 31, 2027?
Bar length is share of the stake; the longest is 9.8%. The second rule marks an equal split.
All 13 bets, and how each is sized.
Think something different? Price it.
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