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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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Asia Morning Briefing: BTC Slips Below $110K as ‘Signs of Fatigue’ Emerging

Good Morning, Asia. Here’s what’s making news in the markets:
Welcome to Asia Morning Briefing, a daily summary of top stories during U.S. hours and an overview of market moves and analysis. For a detailed overview of U.S. markets, see CoinDesk’s Crypto Daybook Americas.
Bitcoin is trading below $110,000, changing hands at $109.7K, as Asia continues its trading week.
The move challenges a prevailing market narrative of summer stagnation, coming on the heels of a note from QCP Capital that emphasized suppressed volatility and a lack of immediate catalysts.
A recent Telegram note from QCP pointed to one-year lows in implied volatility and a pattern of subdued price action, noting that BTC had been “stuck in a tight range” as summer approaches.
A clean break below $100K or above $110K, they wrote, would be needed to “reawaken broader market interest.”
Even so, QCP warned that recent macro developments had failed to spark directional conviction.
“Even as US equities rallied and gold sold off in the wake of Friday’s stronger-than-expected jobs report, BTC remained conspicuously unmoved, caught in the cross-currents without a clear macro anchor,” the note said. “Without a compelling narrative to spark the next leg higher, signs of fatigue are emerging. Perpetual open interest is softening, and spot BTC ETF inflows have started to taper.”
That context makes the current move all the more surprising.
Over the weekend, Bitcoin surged 3.26% from $105,393 to $108,801, with hourly volume spiking to 2.5x the 24-hour average, according to CoinDesk Research’s technical analysis model. BTC broke decisively above $106,500, establishing new support at $107,600, and continued upward into Monday’s session, reaching $110,169.
The breakout coincides with a tense macro backdrop: US-China trade talks in London and a $22 billion U.S. Treasury bond auction later this week have injected uncertainty into global markets. While these events could drive fresh volatility, QCP cautioned that recent headlines have mostly led to “knee-jerk reactions” that quickly fade.
The question now is whether BTC’s move above $110K has true staying power, or whether the rally is running ahead of the fundamentals.
A ‘Massive Shift’ in Institutional Staking May Drive ETH’s Next Rally
Ethereum’s critics have long highlighted centralization risks, but that narrative is fading as institutional adoption accelerates, infrastructure matures, and recent protocol upgrades directly address past limitations.
“Market participants will pay for decentralization because it’s in their economic interest from a security and principal protection standpoint,” Mara Schmiedt, CEO of institutional Ethereum staking platform Alluvial, told CoinDesk. “If you look at [decentralization metrics] all of these things have massively improved over the last couple of years.»
There’s currently $492 million worth of ETH staked by Liquid Collective – a protocol co-founded by Alluvial to facilitate institutional staking
While this figure may appear modest compared to Ethereum’s total staked volume of around $93 billion, what’s interesting is that it originates predominantly from institutional investors.
«We’re really on the cusp of a truly massive shift for Ethereum, driven by regulatory momentum and the ability to unlock the advantages of secure staking,» she noted.
Central to Ethereum’s institutional readiness is the recent Pectra upgrade, a significant development Schmiedt describes as both «massive» and «underappreciated.»
«I think Pectra has been a massive upgrade. I actually think it’s been underappreciated, just in terms of the tremendous amount of change it introduces into the staking mechanics,» Schmiedt said.
Additionally, Execution Layer triggerable withdrawals—a key component of Pectra—provide institutional participants, including ETF issuers, a crucial compatibility upgrade.
This feature enables partial validator exits directly from Ethereum’s execution layer, aligning with institutional operational requirements such as T+1 redemption timelines.
«EL triggerable withdrawals create a much more effective path to exit for large-scale market participants,» Schmiedt added.
Ultimately, Schmiedt said, «I think we’ll see that a lot more [ETH] in institutional portfolios going forward.”
News Roundup
Trump Media May Be the Cheapest Bitcoin Play Among Public Stocks, NYDIG Says
Trump Media (DJT) may be one of the cheapest ways to get bitcoin exposure in public markets, according to a new report from NYDIG, CoinDesk recently reported.
As a growing number of companies adopt MicroStrategy’s strategy of stacking BTC on their balance sheets, analysts are rethinking how to value these so-called bitcoin treasury firms.
While the commonly used modified net asset value (mNAV) metric suggests that investors are paying a premium for BTC exposure, NYDIG’s Greg Cipolaro argues mNAV alone is “woefully deficient.” Instead, he points to the equity premium to NAV, which factors in debt, cash, and enterprise value, as a more accurate gauge.
By that measure, Trump Media and Semler Scientific (SMLR) rank as the most undervalued of eight companies analyzed, trading at equity premiums of -16% and -10% respectively, despite both showing mNAVs above 1.1. In other words, their shares are worth less than the value of the bitcoin they hold.
That’s in stark contrast to MicroStrategy (MSTR), which rose nearly 5% Monday as bitcoin crossed $110,000, while DJT and SMLR remained mostly flat—making them potentially overlooked vehicles for BTC exposure.
Circle Stock Nearly Quadruples Post-IPO as Bitwise and ProShares File Competing ETFs
Two major ETF issuers, Bitwise and ProShares, filed proposals on June 6 to launch exchange-traded funds tied to Circle (CRCL), whose stock has nearly quadrupled since its IPO late last week, CoinDesk previously reported.
ProShares is aiming for a leveraged product that delivers 2x the daily performance of CRCL. At the same time, Bitwise plans a covered call fund that generates income by selling options against held shares, two very different ways to capitalize on the stock’s explosive rise.
CRCL surged another 9% Monday in volatile trading, continuing to draw interest from both traditional finance and crypto investors. The proposed ETFs have an effective date of August 20, pending SEC approval. If approved, they would further blur the lines between crypto and conventional finance, giving investors new tools to play one of the hottest post-IPO names of the year.
Market Movements:
- BTC: Bitcoin is trading at $109,795 after a 3.26% breakout fueled by institutional buying, elevated volume, and macro uncertainty from US-China trade talks and an upcoming $22B Treasury auction.
- ETH: Ethereum rebounded 4.46% from a low of $2,480 to close at $2,581, with strong buying volume confirming support at $2,580 and setting up a potential breakout above $2,590.
- Gold: Gold is trading at $3,314.45, edging up 0.08% as investors watch US-China trade talks in London and a subdued dollar keeps prices attractive.
- Nikkei 225: Asia-Pacific markets rose Tuesday, with Japan’s Nikkei 225 up 0.51%, as investors awaited updates from ongoing U.S.-China trade talks.
- S&P 500: The S&P 500 closed slightly higher Monday, boosted by Amazon and Alphabet, as investors monitored U.S.-China trade talks.
Elsewhere in Crypto
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Bitcoin Climbs Above $110K, ‘At Crossroads’ for Next Major Move

Bitcoin’s BTC quiet climb on Monday accelerated to its strongest price in June, rebounding from last week’s decline to near all-time high levels.
The largest crypto advanced by 3.7% over the past 24 hours, topping $110,000, and it’s changing hands by only 2% from its record prices observed in May. Ethereum’s ether ETH kept pace with a 3.8% gain during the same period, bouncing above $2,620. Native tokens of Hyperliquid HYPE and SUI SUI outperformed most large-cap cryptocurrencies, rising 7% and 4.5%, respectively.
Bitcoin’s move higher caught leveraged traders off-guard, liquidating over $110 million worth of short positions within an hour, CoinGlass data shows. Across all crypto assets, some $330 million of shorts were liquidated during the day, the most in a month. Shorts are seeking to profit from declining asset prices.
The move happened while traditional markets showed muted action, with the S&P 500 and Nasdaq indexes flat on the day. Crypto-related stocks bounced during the session to catch up with BTC’s recovery over the weekend.
«A ‘peaceful rally’ is a perfect way to describe this price action,» said well-followed analyst Caleb Franzen, founder of Cubic Analytics. «Just a consistent development of higher highs and higher lows. Any signs of weakness? Buyers step in and defend the trend.»
The crypto market is now on steadier footing for a potential next leg higher after bitcoin’s 10% decline to near $100,000 and with more than $1.9 billion in liquidations across crypto derivatives over the past week, having flushed excessive leverage, Bitfinex analysts noted in a Monday report.
However, on-chain data indicates rising sell pressure from long-term holders that could overwhelm demand, the analysts added.
“Bitcoin is now at a crossroads—balanced between structural support and waning bullish momentum, waiting for its next macro cue,” the Bitfinex note added.
Those macro catalysts may come later this week, noted Jake O, OTC trader at crypto trading firm Wintermute.
«U.S. and Chinese trade representatives are scheduled to meet today, with markets likely sensitive to any headlines following last week’s positive momentum, and the data calendar remains light until Wednesday, when CPI will offer fresh insight into U.S. inflation,» he said.
UPDATE (June 9, 21:51 UTC): Adds short liquidation data from CoinGlass.
Uncategorized
Aptos’ APT Gains 4% on Significant Volume, Has More Potential Upside

Aptos’ APT token rallied more than 4% on significant volume, with momentum indicators suggesting more potential upside, according to CoinDesk Research’s technical analysis model.
The digital asset broke out of its consolidation phase between $4.65-$4.73, establishing strong support at $4.73 before pushing through previous resistance levels to establish a new local high, according to the model.
The token is currently 2.6% higher, trading around $4.86.
The broader market gauge, the CoinDesk CD20 was 1.75% higher at publication time.
Technical Analysis:
- APT rallied from $4.65 to $4.85, representing a 4.3% gain with significant volume confirmation.
- Price formed a clear consolidation pattern between $4.65-$4.73 before experiencing a decisive breakout at 09:00 with volume nearly doubling the 24-hour average.
- Strong support established at $4.73 with subsequent price action forming an ascending channel with resistance at $4.85.
- Substantial volume spike during the 16:00 candle (884,397 units) confirmed buyer conviction as APT pushed through previous resistance levels.
- Price formed a distinct pattern of higher lows while encountering resistance at $4.85, which was breached during the 20:01 candle with significant volume (10,126 units).
- Key technical development occurred at when price surged from $4.84 to $4.85 with strong volume confirmation (9,094 units).
- Support at $4.84 held through subsequent retests, with final minutes showing decisive momentum suggesting potential continuation of the uptrend.
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