GameSquare Holdings just spent $5.15 million on CryptoPunk #5577, a pixelated ape wearing a cowboy hat. The gaming company bought one of only 24 ape punks in the 10,000-piece collection from Compound founder Robert Leshner, who originally paid $9.4 million for it in 2022. GameSquare plans to use the NFT as collateral to borrow stablecoins and generate yield. Their stock jumped 72% after the announcement, proving investors love expensive digital cowboys more than expected.
GameSquare Holdings just dropped $5.15 million on a cartoon ape wearing a cowboy hat. Welcome to 2025, where publicly traded companies are buying JPEGs for their treasury.
Welcome to 2025, where publicly traded companies are buying cartoon apes for their corporate treasury instead of bonds.
The NFT in question is CryptoPunk #5577, dubbed “Cowboy Ape.” It’s one of only 24 ape punks in the entire 10,000-piece collection. That makes it rarer than most things people actually need.
GameSquare didn’t pay cash. Instead, they structured the deal using 3,433,333 preferred shares, convertible to common stock at $1.50 per share. The seller? Robert Leshner, founder of Compound and CEO of Superstate. Guy knows his way around DeFi, apparently also knows when to cash out of monkey pictures.
Leshner bought this thing in 2022 for 2,501 ETH, which was worth $9.4 million at the time. He just sold it for $5.15 million. Math is brutal sometimes.
But GameSquare isn’t just collecting digital art for the culture. CEO Justin Kenna calls this a “grail” asset, part of their broader strategy to use NFTs as yield-generating treasury assets. The plan involves leveraging the punk through crypto firm Dialectic to borrow stablecoins at fixed rates, then reinvesting those funds to capture a spread. They keep the NFT, make money on borrowed cash. Clever, if it works.
The company already holds 12,900 ETH worth about $48 million as of July. They’re clearly betting big on crypto assets. The acquisition follows a July 2025 approval for a $10 million allocation to an NFT yield strategy. The timing aligns with a broader NFT market revival, as CryptoPunks recently hit a 48 ETH floor price.
CryptoPunk #5577 stands out even among rare apes. It has the cowboy hat attribute, shared by only 142 punks total. Plus it’s one of just 333 punks with a single attribute. The combination of ape plus cowboy hat makes it special, even in a collection where pixelated faces sell for millions.
GameSquare’s stock jumped 72% after announcing the deal. Investors seem to like the NFT treasury strategy, or at least the headlines it generates.
The transaction reflects a broader trend of public companies integrating high-value NFTs into their capital structures. Whether buying cartoon apes for corporate treasury makes long-term sense remains to be seen. But GameSquare is clearly committed to finding out.
