Peter Schiff’s Bitcoin Bet Backfires: Strategy’s Crypto Gamble Ranks 6th Worst in S&P 500 for 2025

Gold bug's digital asset pivot turns into a cautionary tale for traditional finance dipping toes into crypto waters.

The Contrarian's Costly Flip

Peter Schiff built his reputation trashing Bitcoin as digital fool's gold. His firm's surprising pivot toward cryptocurrency exposure in 2025 became the year's most ironic financial plot twist—and one of its most expensive lessons.

When Hedges Become Anchors

The strategy's performance landed it squarely among the S&P 500's bottom ten, proving that adding crypto volatility to a traditional portfolio can sometimes look less like diversification and more like self-sabotage. Timing, as they say on Wall Street, is everything—except when it's not.

The Institutional Crypto Conundrum

Schiff's firm isn't alone in struggling to harness crypto's upside while dodging its legendary drawdowns. The episode highlights the ongoing challenge for traditional asset managers: how to capture blockchain's disruptive potential without getting disrupted themselves.

One cynical take? This is what happens when gold-standard thinking meets a digital asset that refuses to follow any playbook but its own. Sometimes the loudest critics make the most expensive converts—and the market collects its tuition one way or another.

Economist Peter Schiff has once again criticized companies that anchor their balance sheets to Bitcoin, this time singling out Strategy. Citing the firm’s stock decline in 2025, Schiff argued that heavy dependence on Bitcoin can erode shareholder value during market downturns.

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