Illinois Just Made Crypto Its Newest 0.2% Side Hustle — Saylor Calls It a "Big Mistake" 🤦

Strategy co-founder Michael Saylor has publicly criticized Illinois' new digital asset tax, one week after Governor JB Pritzker signed the legislation into law. In a post on X, Saylor described the move as a "Big Mistake," joining a growing chorus of industry pushback against the measure.

The Digital Asset Privilege Tax Act, signed by Pritzker, imposes a 0.2% levy on crypto transactions, including transfers between wallets. The tax takes effect January 1, 2027, and is projected to generate up to $60 million in state revenue. The law also introduces a separate 1.75% levy on sports bets placed on prediction market platforms such as Polymarket, expanding the state's reach over emerging digital asset venues.

The tax has intensified an already fraught relationship between Illinois and the crypto industry. The state is currently facing a lawsuit from the Commodity Futures Trading Commission, which is seeking to defend its exclusive jurisdiction over prediction markets. Illinois had previously issued cease-and-desist letters to Polymarket and Kalshi in an effort to enforce its gambling laws, setting up a legal collision with federal regulators.

Other industry stakeholders have echoed Saylor's criticism of the tax, arguing it could push crypto activity and investment out of the state. The Illinois revenue projection assumes continued transaction growth, though critics note the levy applies even to non-commercial wallet-to-wallet transfers, broadening its scope beyond taxable investment activity. The measure arrives as Congress moves to draft a federal framework for taxing digital asset transactions, raising questions about how state-level rules will interact with any national standard.

Saylor's "Big Mistake" remark is the latest in a series of public disputes between Strategy's leadership and state-level crypto policies, reflecting heightened scrutiny of how U.S. states plan to tax digital assets amid a still-developing federal regulatory landscape.