The Department of Justice filed a federal criminal complaint on May 27, 2026 against Michele Spagnuolo — screen name "AlphaRaccoon" — a 36-year-old Italian citizen residing in Switzerland who worked as a Staff Information Security Engineer at Google since 2014. He used an internal search-trend tool to access data before it went public, then converted that information into Polymarket positions. Criminal complaint: 26 MAG 2020 (SDNY). The CFTC filed a parallel civil complaint the same day: 1:26-cv-04419 (SDNY). He appeared before U.S. Magistrate Judge Sarah Netburn. Bond: $2.25 million secured by $1 million cash. No plea entered. He is the second federal criminal case tied to Polymarket. The DOJ called it insider trading.
That criminal complaint was filed on the same calendar day as three unusual options positions in energy stocks. The same day Trump threatened to bomb a US ally in a cabinet meeting. The same day the highest volume-to-open-interest ratio in this investigation's dataset appeared in Devon Energy options with no public catalyst.
The DOJ knows the playbook. They just charged someone for it. In the same markets. On the same day.
The casino is still open.
I. What AlphaRaccoon Proved
Polymarket
inside data
counts
(wire fraud)
Spagnuolo's mechanism: Google's internal search-trend tool showed volume data before public release. From October 15 through December 4, 2025, he risked $2,754,092 on Polymarket contracts tied to Google's internal information and profited approximately $1.2 million. His specific documented bet: singer d4vd would be Google's most-searched person in 2025 — confirmed from internal data before Google published its annual Year in Search results. Casino Series →⁵
Three charges: one count violating the Commodity Exchange Act (maximum 10 years), one count wire fraud (maximum 20 years), one count money laundering (maximum 20 years). Prosecuted by AUSAs Thomas Burnett, Ryan B. Finkel, and Allison Nichols. The CFTC filed a parallel civil complaint the same day. Magistrate Judge Sarah Netburn. $2.25 million bond. No plea entered.
The structure of what this investigation has documented since March 23, 2026 is not elementary. It is larger. But it is the same structure.
Someone with advance knowledge of US policy decisions — ceasefire announcements, Hormuz reopening signals, Treasury sanctions against a Gulf ally — converted that knowledge into positions in regulated derivatives markets. Four instances documented in crude oil futures. Three in equity options. The instruments are different. The architecture is identical. The minutes-before-announcement windows are on record. Iran Intel →³
The Commodity Futures Trading Commission has jurisdiction over all of it. The CFTC has one commissioner. His previous clients were crypto firms and prediction markets. His staff is at its lowest level since 2009. On May 27 — the same day AlphaRaccoon was charged — the CFTC was not watching.
II. Three Positions, One Day
May 27, 2026 is now a documented date in this investigation.
The OXY put position. At a cabinet meeting on May 27, the President of the United States threatened to "blow up" Oman — a US ally — if it participated in a joint Iran-Oman Strait of Hormuz management arrangement. Occidental Petroleum's Block 53 concession — 800 million barrels — is in Omani territory. The OXY CEO's successor for Middle East operations, Richard A. Jackson, takes the portfolio June 1. On the same session, 1,000 September $55 OXY puts were placed. Two days later, Treasury Secretary Bessent formally sanctioned the Persian Gulf Strait Authority and Oman retreated. OXY closed at $56.63, down 1.20%, and fell further after hours to $56.56. The September put block is directionally confirmed — oil-decline thesis on deal close, not the bombing scenario. OXY Suspects →¹
The person who placed those puts on May 27 had two days' lead on a Treasury Secretary's direct conversation with an Omani Ambassador. That conversation was not public.
DVN 1,948.7× volume-to-open-interest. This is the highest ratio in this investigation's dataset, across every ticker, every session, since February 28. It appeared in Devon Energy options on May 27 with no matching public catalyst. No Form 4 has been logged for May 27 DVN transactions. The EDGAR window for those filings is open June 1 through June 3.
CVX June 18 $145 calls. These did not appear May 27. They appeared on the evening of May 29 — the same evening the New York Times confirmed that the Iran MOU draft contains a $300 billion reconstruction fund that explicitly invites US energy companies into Tehran for joint ventures. The June 18 expiry falls after the EDGAR Form 4 window, after the GAESA deadline, and after the Polymarket/Kalshi records deadline. Someone placed a large bet that Chevron rises significantly before June 18. That bet lands in the same week the Iran deal either resolves or collapses.
Three positions. Three different instruments. Three different thesis structures. All within a 48-hour window around the Oman fracture.
III. The March 1 Template
March 1, 2026: United States military operations against Iran begin. Eight Occidental Petroleum executives file SEC Form 4 transactions on the same calendar day. All score 16/20 on this investigation's suspicion metric. Richard A. Jackson is on that list. He is the same executive who takes over Occidental's Middle East portfolio on June 1, 2026 — the same day the EDGAR Form 4 window opens for May 27 transactions. Iran Intel →³
The template is documented. The pattern is on record. The question June 3 answers is whether it repeated.
If Jackson filed a Form 4 for a May 27 transaction — the day Trump threatened Oman, the day OXY puts were placed in the same session, the day his succession was confirmed — that is not a coincidence. That is the same filing, in the same company, by the same executive, with the same pattern signature, on the same category of event. Different date. Same architecture.
IV. The CVX Signal — Hess and the Call Block
This section received a material upgrade after the original draft was written. It is the strongest confirmed signal in this story.
John B. Hess — director of Chevron, son of the founder of Hess Corporation, whose company was acquired by Chevron — sold approximately $109 million in CVX shares in two tranches in May 2026. Both sales were discretionary. Neither was a pre-scheduled 10b5-1 plan. The Form 4 filings confirm this.
On the evening of May 29 — fourteen days after Hess's second tranche, and the same evening the NYT confirmed the $300 billion Iran MOU reconstruction fund — 8,333 CVX June 18 $145 calls appeared. Volume-to-open-interest: 72.5×. Implied volatility: 82%. The call block represents a large leveraged bet that Chevron rises significantly before June 18.
Someone sold $109 million in Chevron in May. Someone else bought a large call block betting Chevron rises before June 18. Those two positions point in opposite directions. One of them knew something the other did not. The Iran MOU Iran JV thesis — US energy majors including CVX invited into Tehran for joint ventures — is the bridge between them. The call block buyer was positioned for that thesis. The Hess sales occurred before the thesis resolved publicly.
Whether Hess sold because he anticipated the deal closing (sell the news) or because he had independent reasons — that question is now on the record. The call block is on the other side of it. CVX Dashboard →¹
V. June 5 — Three Threads
Compliance gives Casino Part Three a new evidence layer. Defiance or an extension request on June 5 is the dispatch signal.
VI. The Binary
This Old Goat has been asked — by readers, in correspondence — what the OXY put position proves. The question is the right question.
It proves that someone placed 1,000 September $55 OXY puts on May 27, 2026. What it does not prove is which outcome they anticipated.
The position profits in two scenarios. Scenario A: Trump bombs Oman. OXY Block 53 goes offline or is threatened. OXY crashes. Puts print. Scenario B: Oman retreats. A deal closes. Hormuz reopens. Oil falls on deal-close news. OXY falls. Puts print.
Both scenarios were always puts. The put buyer needed only to know that one of the two would happen. The position was not a directional bet on war or peace. It was a bet that Oman's role in the Hormuz standoff would resolve — in either direction — before September.
What May 29 confirmed is which binary resolved. Oman retreated. The PGSA was sanctioned. OXY fell. The oil-decline thesis is directionally confirmed. The put buyer knew that Bessent was going to sanction PGSA — or they knew the Oman threat was sufficiently serious to push oil lower regardless.
Either way: someone knew something that wasn't public on May 27. The CFTC has jurisdiction. The CFTC has one commissioner, 550 staff, and two crypto enforcement cases to its name in this administration.
VII. What Remains Unproven
What is confirmed: three positions on May 27. One closed directionally. Two resolve in seven days. AlphaRaccoon was charged for the same structure in the same markets on the same day. The CFTC is not watching.
VIII. Verdict
The casino did not close when Part Two named the captured regulator. It is operating under the same conditions. The trades are larger. The instruments are more specific. The DOJ has now confirmed that Polymarket is a venue where inside information gets converted to money. They charged a Google engineer for it. They have not charged the platform. The CFTC has not charged anyone for the $3.2 billion oil futures pattern. Michael Selig said enforcement is watching. Gretchen Lowe — thirty years at the CFTC, forced out — said something different.
The window opened June 1. It closes June 3.