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From Early Michael Saylor Bet to Billions in Deals: How Jefferies Became a Crypto Powerhouse

It all started in 2019, when a relatively small software company called MicroStrategy (now known as Strategy) knocked on investment bank Jefferies’ door after being turned away by Wall Street giants.
At the time, Michael Saylor’s firm had a market cap of nearly $2 billion and was looking to raise capital to buy bitcoin—something bulge bracket banks were reluctant to support.
Jefferies took a chance on Saylor, marking a pivotal deal for the investment bank and the digital assets sector.
Now, Saylor’s firm is worth about $111 billion in market cap, other companies are buying bitcoin for their balance sheets, and large Wall Street firms are piling into the digital assets sector.
And Jefferies? The firm is now a full-service investment bank for the crypto and blockchain space, and it’s doing billions in deals without the crutch of a trillion-dollar balance sheet or FDIC-insured deposits.
“We don’t change our stripes too often, but when we see opportunity, we move fast,” Alexander Yavorsky, head of FIG investment banking at Jefferies, told CoinDesk in an interview.
The crypto commitment
The game-changing MicroStrategy engagement in 2019 kickstarted a much deeper foray into the asset class for Jefferies.
By 2020, Jefferies had become the first major full-service investment bank to dedicate a senior banker exclusively to crypto. Tim O’Shea, now co-head of digital assets coverage, spends 100% of his time on the asset class.
But don’t call them a crypto shop as Jefferies has been consistently doing deals across the board, putting the firm sixth globally in the last twelve months, according to data from Dealogic.
Diving deeper into deals that Jefferies worked on, the firm revealed that it has advised on 120 transactions with over $150 billion of deal value across fintech, market structure, and exchanges since 2015.
This track record, particularly handling deals that involve applied technology and complex regulatory footprints, uniquely equipped Jefferies to handle the hybrid world where crypto meets traditional finance.
“We are a full-service investment banking firm, rather than a crypto shop,” Yavorsky said, «but we’ve built deep sector knowledge, and we know how to structure deals and move quickly.»
Over the past three years, Jefferies has steadily increased its involvement in crypto and crypto-adjacent dealmaking, building a track record across capital markets, M&A, and restructuring.
One of the standout deals the firm advised was NinjaTrader on its $1.5 billion acquisition by Kraken, a notable example of consolidation between traditional trading platforms and digital asset exchanges.
The Jefferies team brings the «incredible expertise and talent required to advise on transactions of this size, they are incredibly dialed into the crypto and capital markets universes,» Martin Franchi, CEO of NinjaTrader, told CoinDesk in an email statement.
«Understanding the needs of folks in the space were native to how they think and in our case, helped bring together the worlds of TradFi and DeFi for a highly strategic deal that benefits not only both firms, but also our customers,” Franchi added.
Navigating complex world of crypto
What really set Jefferies apart is that the investment bank didn’t just stick to the usual deal-making advisory for the industry. With an industry as dynamic as crypto, the bank stayed nimble to take on a much more complex mandate.
It played a key role in one of the industry’s most high-profile collapses, serving as adviser to the Official Committee of Unsecured Creditors in the FTX bankruptcy, where it worked to help recover value for stakeholders.
Meanwhile, the bank continued supporting traditional financial institutions that entered the crypto space.
It advised J.C. Flowers on its investment in LMAX, and worked with Victory Park Capital on the SPAC merger with Bakkt.
Beyond advisory roles, Jefferies has executed capital raises for major players like Galaxy Digital (GLXY) and DRW, and has been active in the crypto mining sector through multiple fundraising and advisory engagements.
The firm has also provided strategic advice on a range of crypto exchange transactions, reflecting its broader involvement in infrastructure and market structure developments within digital assets.
A growing influence
Though not a crypto-exclusive investment bank, Jefferies’ activity in the sector points to a growing comfort with the complexities of digital asset finance, and a willingness to engage where traditional firms have often hesitated.
With the lines between centralized and decentralized finance continuing to blur, and infrastructure firms increasingly in M&A crosshairs, Jefferies looks poised to remain one of the most active and experienced investment banks in the digital asset space.
Read more: Bitcoin Mining Profitability Down 7.4% in March as Prices, Transaction Fees Fell: Jefferies
Disclaimer: Parts of this article were generated with the assistance from AI tools and reviewed by our editorial team to ensure accuracy and adherence to our standards. For more information, see CoinDesk’s full AI Policy.
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Ether Nears $2.7K, Dogecoin Zooms 9% as Crypto Market Remains Cheery

Ether (ETH) and dogecoin (DOGE) led majors gains on Wednesday with a 9% jump in the past 24 hours, extending a bullish streak that’s seen both tokens gain double digits over the past week.
The broader crypto market showed modest gains with total capitalization up 1.7%, per CoinGecko, with bitcoin (BTC) hovering around $103,700 in Asian morning hours.
Ethereum traded above $2,600, with dogecoin around 24 cents. XRP, BNB Chain’s BNB, Cardano’s ADA and Solana’s SOL gained between 3%-5%.
Despite a burst of green across major altcoins, crypto traders are starting to feel the weight of macro markets and warn of profit-taking in the short term. A stronger dollar and renewed trade tensions temper momentum, even as bitcoin flirts with record territory.
“The strengthening dollar on news of tariffs has been a natural drag on cryptos,” explained Alex Kuptsikevich, chief market analyst at FxPro, in an email to CoinDesk. “This is doubly true due to bitcoin’s proximity to the highs, reinforcing the pull for short-term profit taking after rallying in just over a month.”
As global markets shift from protectionism to cautious optimism, bitcoin remains in limbo. The asset is once again caught between competing narratives for some trader.
«BTC remains caught in a tug-of-war between its identity as “digital gold” and its function as a risk-on proxy,» traders at Singapore-based QCP Capital said in a market broadcast. «This tension continues to obscure its directional conviction. As the macro narrative moves from protectionism toward renewed trade optimism, BTC could remain range-bound.»
Still, sentiment remains strong. The widely-tracked Fear & Greed Index has held steady above 70 for four consecutive days — a “greed” level typically associated with sustained bullish appetite in the near term.
“Bitcoin showed its unpredictable nature on Monday,” Kuptsikevich added. “But with the positivity remaining, it’s worth paying attention to the price dynamics near $105. Will we see an acceleration or a new failure? The answer will guide the coming days.”
Elsewhere, latest fund flow data from CoinShares shows $882 million in institutional inflows last week — the third straight week of strong buying.
BTC led with $867 million, while ETH saw just over $1.8 million in flows despite a stellar price performance over the last week. Notably, Solana (SOL) posted $3.4 million in outflows, even as traders loaded up on $200 call options expiring in late June, as reported.
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Slow Blockchain Governance Leaves Crypto Exposed to Quantum Threats

Quantum computing poses a real threat to crypto, and slow-moving governance processes risk leaving blockchains vulnerable, according to Colton Dillion, a co-founder of Quip Network, which provides quantum-proof vaults for storing digital assets.
While the technology, which uses the quantum states of subatomic particles to perform calculations instead of transistors and binary code, is still in its infancy, companies including Google and Microsoft are pressing forward with research and development. The goal is a massive step-up in speed that makes tough calculations like cracking encryption, such as that used to protect blockchains, faster and simpler.
And when quantum computing becomes available, any attacker is unlikely to announce their presence immediately.
“The threat won’t start with Satoshi’s keys getting stolen,» Dillion said in an interview. “The real quantum attack will look subtle, quiet, and gradual, like whales casually moving funds. By the time everyone realizes what’s happening, it’ll be too late.»
Dillion’s doomsday scenario involves a quantum-computing-powered double-spend attack. In theory, quantum computing could reduce the mining power required for a traditional 51% attack down to about 26%, Dillion said.
«So now you’ve compromised the 10,000 largest wallets. You rewind the chain, liquidate those 10,000 largest wallets, then double spend all the transactions, and now you’ve really got a nuclear bomb,” is how he imagines it.
The industry, of course, is working to find a solution.
Bitcoin developer Agustin Cruz, for instance, proposed QRAMP, a Bitcoin Improvement Proposal (BIP) that mandates a hard-fork migration to quantum-secure addresses. Quantum startup BTQ has proposed replacing the proof-of-work consensus system that underpins the original blockchain entirely with quantum-native consensus.
The problem is that the proposals must gain community approval. Blockchain governance, such as Bitcoin Improvement Proposals (BIPs) and their Ethereum equivalents, Ethereum Improvement Proposals (EIPs), tends to be rife with politics, making it a long, inherently cautious process.
For example, the Bitcoin community’s recent resolution on the OP_RETURN function was years in the making, with months of developer debates about what’s considered the «proper» use of the blockchain. Ethereum’s upgrades, like the Merge, also faced lengthy debates and delays.
Dillion argues that the governance process leaves crypto dangerously exposed because quantum computing threats will evolve much faster than the protocols can respond.
“Everyone’s trying to do this from the top down by starting with a BIP or an EIP and getting everyone’s buy-in together. But we think that this is a very difficult, heavy lift,” he said.
Quip Network’s quantum-proof vaults aim to circumvent the political inertia by allowing immediate user-level adoption without requiring protocol upgrades. The vaults leverage hybrid cryptography, blending classical cryptographic standards with quantum-resistant techniques to provide blockchain-agnostic security.
Effectively, they allow the whales, holders of large amounts of a cryptocurrency, to secure their stashes while waiting for the machinations of blockchain governance to get it together. Crypto communities can’t afford leisurely debates, he argues.
“The BIP and EIP processes are great for governance, but terrible for rapid threat response,” said Dillion. «When quantum hits, attackers won’t wait for community consensus.”
Colton Dillon is speaking at the IEEE Canada Blockchain Forum, part of Consensus 2025 in Toronto. The IEEE is a Knowledge Partner of Consensus.
Read more: Quantum Computing Group Offers 1 BTC to Whoever Breaks Bitcoin’s Cryptographic Key
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EToro Goes Public At $52 A Share, Far Exceeding Marketed Range

Shares of stock and crypto trading platform eToro (ETOR) have debuted at $52 a share after the company hit the Nasdaq exchange on Tuesday evening.
The company raised about $310 million from investors as it sold 6 million shares at a price of $52 a piece. The listing values the company at $4.2 billion.
The price is significantly higher than the marketed range, as the company received a much higher demand than previously anticipated.
EToro becomes the first company to go public after a rough couple of months in markets across the U.S., as President Donald Trump is in discussions to make several tariff deals with leaders around the world.
Because of that, many companies, including eToro, had delayed going public, but Bloomberg reported last week that the trading platform was resuming plans.
The company will trade under the ticker “ETOR”.
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