Barry Silbert Makes Crypto Comeback: Reclaims Grayscale Chairmanship Post-Legal Exit

Grayscale just got its old captain back—whether Wall Street likes it or not.

Silbert’s back. The Digital Currency Group founder—who stepped down amid 2023’s regulatory firestorm—just reclaimed his throne at the world’s largest crypto asset manager. No explanations, no apologies. Classic Barry.

Why now? Probably because Bitcoin’s flirting with $100K again and institutions are crawling back to crypto like hedge funds to a tax loophole.

Grayscale’s been bleeding assets since the SEC lawsuit, but Silbert’s return screams confidence. Either that, or he knows something the rest of us don’t (again).

One thing’s certain: When crypto’s most notorious survivor makes a move, the market listens. Even if half his bets end up in bankruptcy court.

TLDR

• Barry Silbert returns as Grayscale chairman after stepping down in 2023 due to legal issues with New York Attorney General
• Grayscale hires four Wall Street veterans for key executive roles including COO, CMO, and communications chief
• The company manages over $35 billion in assets and generates $268.5 million annually from its Bitcoin ETF despite market share decline
• Grayscale filed confidentially for an IPO last month while legal case with NY regulators continues
• The leadership changes come as crypto firms increasingly recruit traditional finance talent for mainstream adoption

Grayscale Investments has reappointed founder Barry Silbert as board chairman and hired four Wall Street veterans to key executive positions. The moves come as the crypto asset manager seeks to strengthen its position in the competitive ETF market.

Silbert returns to the chairman role after stepping down in December 2023. His departure followed a lawsuit from the New York Attorney General’s office that accused Silbert and parent company Digital Currency Group of misleading investors and hiding over $1 billion in financial losses. Both Silbert and DCG denied the claims, and the case remains ongoing in New York state court.

The company has expanded its leadership team with four new hires from traditional finance. Diana Zhang joins as chief operating officer, Ramona Boston as chief marketing officer, Andrea Williams as chief communications officer, and Maxwell Rosenthal as chief human resources officer. All four executives report to Grayscale CEO Peter Mintzberg.

The new executives come from established Wall Street firms including Bridgewater, Apollo, Goldman Sachs, and Citadel. Their hiring reflects a broader trend of crypto companies recruiting traditional finance talent as the industry prepares for mainstream adoption.

Grayscale manages over $35 billion in assets across four crypto ETFs. The company launched the first publicly traded Bitcoin investment vehicle in the US through its Bitcoin Trust in 2015. Since then, it has converted both its Bitcoin and ethereum trusts into ETFs.

Financial Performance Despite Competition

The company’s spot Bitcoin ETF generates $268.5 million in annual revenue, more than any other Bitcoin ETF. This performance stems largely from its 1.5% fee structure, which is up to six times higher than competitors like BlackRock’s IBIT or Fidelity’s FBTC.

Grayscale’s market share has dropped to about 5% of the US spot bitcoin ETF market. The company has experienced over $21 billion in outflows as investors moved to lower-cost alternatives. However, its higher fees allow it to maintain revenue leadership despite the smaller market share.

Silbert expressed confidence in the company’s direction. “When I founded Grayscale in 2013, we saw an enormous opportunity to pioneer a new model for accessing and investing in digital assets,” he said. “Today, I continue to have DEEP conviction in the company’s long-term positioning and in the leadership team guiding it forward.”

Industry-Wide Talent Migration

Other crypto companies are following similar hiring strategies. In 2024, Kraken hired Gilles BianRosa from neobank N26 as chief operating and product officer. The exchange also brought in Marcus Hughes from Morgan Stanley and Coinbase as global head of regulatory strategy.

Galaxy Digital has recruited traditional finance talent for institutional expansion. The firm hired Tony Paquette, former chief financial officer at hedge fund Point72 and ex-JPMorgan executive, as its CFO in late 2024.

Galaxy Digital secured a UK derivatives trading license in early 2025. The firm expanded its London presence to serve global institutional clients.

DCG’s chief financial officer Mark Shifke replaced Silbert as chairman in 2023. Shifke will remain on the board alongside Silbert following the leadership transition.

Grayscale filed a confidential submission for an initial public offering last month. The IPO filing proceeds despite the ongoing legal dispute with New York regulators over the alleged investor misleading claims.