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CryptoPodcastsWeekly Roundup 02/20/26 (CFTC Claims Prediction Markets, Rogue AI Agents, ETH's Existential Crisis) (EP.703)
Weekly Roundup 02/20/26 (CFTC Claims Prediction Markets, Rogue AI Agents, ETH's Existential Crisis) (EP.703)
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On The Brink with Castle Island

Weekly Roundup 02/20/26 (CFTC Claims Prediction Markets, Rogue AI Agents, ETH's Existential Crisis) (EP.703)

On The Brink with Castle Island
•February 20, 2026•31 min
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On The Brink with Castle Island•Feb 20, 2026

Why It Matters

These developments signal a pivotal moment for crypto regulation and market stability, with authorities tightening oversight on prediction markets and new legislative efforts shaping the industry’s future. Understanding these shifts helps investors, developers, and policymakers navigate risks and opportunities in a rapidly evolving ecosystem.

Key Takeaways

  • •CFTC asserts jurisdiction over state-regulated prediction markets.
  • •Crypto venture funds raise over $800M, reshaping industry capital.
  • •AI agents now benchmarked for smart‑contract vulnerability detection.
  • •Bitwise seeks ETF approval for election prediction market shares.

Pulse Analysis

The week’s headline was the CFTC’s bold claim of authority over prediction markets, a stance that pits the federal regulator against state gambling boards. By filing an amicus brief and launching a public video campaign, Chair Mike Selye signaled that crypto‑based prediction platforms like Novig and Pred will be treated as commodities, not gambling. This regulatory clarity sparked a surge of capital, with Dragonfly’s $650 million fourth fund and DBA’s $68 million second fund underscoring a renewed investor appetite despite broader market headwinds.

Simultaneously, artificial‑intelligence advances are reshaping security dynamics in crypto. OpenAI and Anthropic’s partnership on the EVM‑Bench benchmark highlights a growing focus on testing AI agents for smart‑contract vulnerabilities. As AI models become capable of autonomously identifying and exploiting code flaws, the industry faces a race between offensive tools and defensive safeguards. Investors are watching closely, recognizing that the next wave of exploits could emerge from sophisticated, publicly accessible AI agents rather than traditional hacker groups.

Product innovation is keeping pace with regulatory and security shifts. Bitwise’s petition for an ETF that tracks 2028 election prediction odds could democratize access to these markets, allowing retail investors to trade outcomes through traditional brokerage accounts. Meanwhile, Gemini’s strategic pivot toward U.S.‑only operations and AI‑driven cost reductions reflects a broader trend of legacy crypto firms consolidating and re‑tooling for compliance and efficiency. Together, these developments illustrate a crypto ecosystem that is simultaneously maturing, confronting new technological threats, and expanding into mainstream financial products.

Episode Description

Matt and Nic are back with another week of news and deals. In this episode: 

Crypto VC funds have some dry powder

CFTC chair Mike Selig asserts jurisdiction over prediction markets relative to the States

Is Kalshi more reliable than interest rate futures?

The CLARITY Act inches closer to passing

Shake up at Gemini

OpenClaw agents are going to start phishing crypto users

Bitwise aims to launch prediction market ETFs

Bridge gets their OCC charter

Hyperliquid launches a lobbying arm

DAT hangover continues

Blockfills reveals a $75m hole

Ethereum is having an identity crisis

Base is moving away from Optimism

Neel Kashkari's bad faith stablecoin criticism

Show Notes

On The Brink with Castle Island

Weekly Roundup 02/20/26 (CFTC claims Prediction Markets, rogue AI agents, ETH’s existential crisis) (EP.703)

Matt and Nic are back with another week of news and deals. In this episode:

  • Neel Kashkari’s bad‑faith stablecoin criticism

  • Base is moving away from Optimism

  • Ethereum is having an identity crisis

  • Blockfills reveals a $75 m hole

  • DAT hangover continues

  • Hyperliquid launches a lobbying arm

  • Bridge gets their OCC charter

  • Bitwise aims to launch prediction‑market ETFs

  • OpenClaw agents are going to start phishing crypto users

  • Shake‑up at Gemini

  • The CLARITY Act inches closer to passing

  • Is Kalshi more reliable than interest‑rate futures?

  • CFTC chair Mike Selig asserts jurisdiction over prediction markets relative to the States

  • Crypto VC funds have some dry powder

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