May 9, 2026
It all started in 2019 when a relatively small software company, MicroStrategy – now known as Strategy – approached investment bank Jefferies after getting the cold shoulder from the big Wall Street banks. Michael Saylor’s company had a market cap of almost $2 billion at the time and was looking for ways to raise capital to buy bitcoin, something that the larger banks were reluctant to do. Jefferies decided to take the risk and start this partnership, a pivotal moment that changed not only the bank, but the digital asset industry.
Now, several years later, Saylor’s company has reached an impressive market value of around $111 billion. Other companies are following suit by adding bitcoin to their balance sheets, while major Wall Street firms are embracing the digital asset sector.
Jefferies has since evolved into a full-fledged crypto and blockchain investment bank, doing billions in deals without the backing of a trillion-dollar balance sheet or FDIC-insured deposits. “We don’t change our core values often, but when we see opportunities, we move quickly,” said Alexander Yavorsky, Jefferies’ chief investment officer.
The partnership with MicroStrategy in 2019 marked the start of Jefferies’ deeper exploration of the asset class. In 2020, the bank became the first major full-service investment bank to dedicate a senior banker exclusively to crypto. Tim Shea, now co-head of digital assets coverage, devotes 100% of his time to the asset class. Don’t call Jefferies a crypto shop, though; the bank has done a wide range of deals and ranked sixth globally over the past year, according to data from Dealogic.
Looking back at the deals Jefferies has been involved with, the bank has advised on 2015 transactions worth more than $120 billion since 150, spanning fintech, market structure, and exchanges. This experience, particularly in complex technology and regulatory environments, makes Jefferies uniquely suited to navigate the hybrid world where crypto meets traditional finance. “We’re a full-service investment bank, not a crypto shop,” Yavorsky emphasized. “We’ve built deep industry 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 related deals, with a proven track record in capital markets, M&A, and restructuring. One of the notable deals the bank was involved in was the $1,5 billion acquisition of NinjaTrader by Kraken, a key example of the consolidation between traditional trading platforms and digital asset exchanges.
What really sets Jefferies apart is that the investment bank doesn’t just offer the usual advisory services to the industry. In a dynamic sector like crypto, the bank remained flexible to take on a much more complex assignment. For example, it played a key role in one of the sector’s most high-profile bankruptcies, advising the Official Committee of Unsecured Creditors during the FTX bankruptcy in an effort to recover value for stakeholders.
At the same time, the bank has continued to support traditional financial institutions entering the crypto space, advising JC Flowers on their investment in LMAX and working with Victory Park Capital on its SPAC merger with Bakkt. In addition to advisory roles, Jefferies has conducted capital raises for major players such as Galaxy Digital and DRW, and has been active in the crypto mining sector through various fundraising and advisory assignments. The bank has also provided strategic advice on numerous crypto exchange transactions, reflecting its broader involvement in infrastructure and market structure developments within digital assets.
While Jefferies isn’t a crypto-exclusive investment bank, the bank’s activities in the sector indicate a growing confidence in the complexities of digital asset finance and a willingness to step in where traditional firms are often reluctant. With the lines between centralized and decentralized finance blurring, and infrastructure companies increasingly in the spotlight of mergers and acquisitions, Jefferies appears well-positioned to remain one of the most active and experienced investment banks in the digital asset space.
What was Jefferies' role in the rise of MicroStrategy?
Jefferies played a critical role in supporting MicroStrategy in 2019, when the bank helped it raise capital to buy bitcoin when larger Wall Street banks balked.
How has Jefferies evolved further in the crypto sector?
Jefferies has been steadily increasing its involvement in crypto, hiring senior bankers focused solely on the asset class, as well as closing major deals and supporting traditional institutions looking to invest in crypto.
What makes Jefferies unique in the world of digital assets?
Jefferies differentiates itself by not only providing advisory services, but also being actively involved in complex deals, and by its willingness to provide innovative solutions in the often turbulent world of crypto finance.
Bitcoin (BTC)
Ethereum (ETH)
XRP (XRP)
