Remember CryptoPunks? This Public Company Just Traded $5.15 Million Worth Of Stock For A JPEG

GameSquare (NASDAQ:GAME) has acquired CryptoPunk #5577 — one of the rarest and most culturally important NFTs — from Compound founder and Superstate CEO Robert Leshner, issuing $5.15 million worth of preferred stock in the exchange.

The purchase was executed through the issuance of GameSquare preferred shares convertible to common stock at $1.50 per share, officially making Leshner a shareholder in the public company.

The move signals GameSquare's deepening commitment to Ethereum-native strategies and positions the firm as a digital asset-forward player in the traditional markets.

CryptoPunk #5577, also known as the "Cowboy Ape," is part of the original 10,000-piece CryptoPunk collection by Larva Labs.

It is one of just 24 "Ape" Punks, and features a distinctive cowboy hat, a trait that has made it one of the most recognizable NFTs in the collection.

Considered a digital artifact, #5577 has long been a part of early trading folklore, memes, and even featured in auction house highlights, making it one of the highest-profile Punks in circulation.

"This isn't just our first grail NFT," said GameSquare CEO Justin Kenna. "It's a signal of how we're thinking differently and expanding our existing footprint in digital culture by building a next-generation media company with crypto in its DNA."

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Robert Leshner, known for his pivotal role in founding Compound and leading Superstate, added, "I'm excited to work with GameSquare as a shareholder, and support Justin and the team as they innovate on the digital-native treasury strategy, in traditional markets and onchain."

The acquisition will serve multiple roles within GameSquare's growing Web3 initiative: it adds to their digital asset treasury, acts as a cultural brand marker, and is slated to be part of the firm's NFT yield program, which targets annualized returns of 6–10%.

GameSquare has also revealed an ongoing collaboration with Superstate to explore tokenization of its equity onchain.

With over $52 million in Ethereum (CRYPTO: ETH) holdings and a $250 million treasury authorization, the company has positioned itself as a top public holder of ETH, integrating digital assets into both balance sheet and brand.

The NFT yield strategy is powered by Dialectic's Medici platform, with NFT management handled in part by 1OF1 AG, led by crypto investor Ryan Zurrer.

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