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MicroStrategy Targeting $2B Perpetual Preferred Stock Offering: Benchmark

The analyst who wrote this piece owns shares of MicroStrategy (MSTR).
Since MicroStrategy (MSTR) become a bitcoin treasury company in August 2020, it has used three primary instruments to acquire bitcoin (BTC): cash on hand, at-the-market (ATM) offerings and convertible bond offerings.
MicroStrategy’s next method of raising capital is to buy bitcoin through perpetual preferred stock, which was announced to the market on Jan. 3. MicroStrategy has announced a capital raise of $2 billion through one or multiple offerings, according to Benchmark.
Benchmark hosted a recent investor meeting with MicroStrategy executive chairman Michael Saylor at the ICR conference in Orlando to discuss the perpetual preferred stock offering.
A perpetual preferred stock typically has no fixed maturity date and continues indefinitely unless the company chooses to redeem it or put a maturity date on it. Shareholders of the stock receive fixed dividend payments but have no voting rights. The company may have the right to buy back the stock at a predetermined price after a specific date. In the case of a liquidation event, perpetual preferred stockholders are paid before common shareholders but after debt holders.
Perpetual stock is an attractive instrument due to a lack of a set maturity date, unlike MSTR’s convertible bonds, where some are already in the money and eligible for conversion. Convertible bonds tend to have a tenor of approximately four to eight years, Saylor said at the conference.
According to the note, Saylor said that the perpetual preferreds were advantageous due to their extended duration. The instrument works as an embedded, indefinite call option in addition to a lump-sum principal payment. The company would benefit as it would be less fragile due to the extended duration of the capital structure.
According to Benchmark, the perpetual preferred stock could achieve a mid-single-digit yield, with low volatility and no-options market, the opposite to a convertible bond.
Perpetual preferreds would be attractive to big institutions like pension funds and banks, as they would receive a stable and fixed dividend payment.
The terms of the perpetual preferred stock have yet to be announced. We do know this is coming in Q1, and the terms of the offering should include dividend payments, convertibility to class A common stock, and provision of redemption of shares according to the MicroStrategy press release on Jan. 3.
Benchmark maintains its buy rating on MSTR with a price target of $650.
As of Monday, MicroStrategy purchased a further 2,530 BTC taking total holdings to 450,000 BTC.
Next week, MicroStrategy’s Special Meeting for Shareholders will take place on Jan. 21. Investors will vote on increasing the authorized class A common stock and preferred stock. MSTR’s Q4 earnings call is set for Feb. 4.
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Canary Capital Files for Tron ETF With Staking Capabilities

Canary Capital is looking to launch an exchange-traded fund (ETF) tracking the price of Tron’s native token, TRX, according to a filing.
The hedge fund submitted a Form S-1 for the Canary Staked TRX ETF with the Securities and Exchange Commission (SEC) on Friday. As the name suggests, the fund — if approved — would stake portions of its holdings.
This would be done through third-party providers, with BitGo acting as custodian for the assets. The fund would track TRX’s spot price using CoinDesk Indices calculations.
A proposed ticker as well as the management fee for the product have not been shared yet.
Issuers had initially filed applications for spot ethereum (ETH) ETFs with the staking feature included but removed them in an amended filing later in order to receive approval from the SEC on their proposals.
While the SEC under former Chair Gary Gensler was strictly against staking, issuers have grown more hopeful that they will be able to add the feature to their spot ether funds, among others, with the appointment of crypto-friendly Chair Paul Atkins.
A decision on a February request from Grayscale to allow staking in the Grayscale Ethereum Trust ETF (ETHE) and the Grayscale Ethereum Mini Trust ETF (ETH) was postponed by the regulator just a few days ago.
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Feds Mistakenly Order Estonian HashFlare Fraudsters to Self-Deport Ahead of Sentencing

Just four months ahead of their criminal sentencing for operating a $577 million cryptocurrency mining Ponzi scheme, the two Estonian founders of HashFlare were seemingly mistakenly ordered to self-deport by the U.S. Department of Homeland Security (DHS) — an instruction that directly contradicted a court order for the men to remain in Washington state until they are sentenced in August.
In a joint letter to the court last week, lawyers for Sergei Potapenko and Ivan Turogin told District Judge Robert Lasnik of the Western District of Washington that both men had received “disturbing communications” from DHS ordering them to leave the country immediately.
“It is time for you to leave the United States,” an email to Potapenko and Turogin dated April 11 read. “DHS is terminating your parole. Do not attempt to remain in the United States — the federal government will find you. Please depart the United States immediately.”
The email, included with the letter filed last week, threatened both men with “criminal prosecution, civil fines, and penalties and any other lawful options available to the federal government” if they stayed in the country. It resembles emails that undocumented immigrants and U.S. citizens alike have received over the past few days.
Ironically, Potapenko and Turogin are not in the U.S. of their own volition — they were extradited from their native Estonia at the request of the U.S. Department of Justice in 2022 on an 18-count indictment tied to their HashFlare scheme. Though they initially pleaded not guilty to all charges, in February they both pleaded guilty to one count of conspiracy to commit wire fraud, which carries a maximum sentence of 20 years in prison, and agreed to forfeit over $400 million in assets. They have both been in the Seattle area on bond since last July.
“Although there is nothing Ivan and Sergei would want more than to immediately go home, they understood that they are also under Court order to remain in King County,” wrote Mark Bini, a partner at Reed Smith LLP and lead counsel for Potenko, wrote in the pair’s joint letter to the court. Bini did not respond to CoinDesk’s request for comment.
In his letter, Bini said DHS’s emails had caused both Potapenko and Turogin «significant anxiety.”
“We and our clients have all seen recent news. Immigration authorities make mistakes, and individuals who should not be in custody end up in custody, sometimes even deported to places where they should not be deported,” Bini wrote.
Six days after Bini’s letter to the judge, the DOJ filed its own letter with the court saying that prosecutors had coordinated with DHS’s Homeland Security Investigations (HSI) division and secured a year-long deferral to the self-deportation order.
“This should provide ample time for the sentencing to take place,” the prosecution’s letter said.
DHS did not respond to CoinDesk’s request for comment.
Potapenko and Turogin are slated to be sentenced on August 14 in Seattle. Their lawyers have said that they will request to be sentenced to time served, meaning no additional time in prison, and to be sent home to Estonia “immediately.”
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CoinDesk Weekly Recap: EigenLayer, Kraken, Coinbase, AWS

Following last week’s tariff-caused drama, this was a relatively quiet week in crypto. Bitcoin remained stable around $84k. The CoinDesk 20, which tracks about 80% of the market, was up about 4% in the last seven days — i.e. nothing historic.
Still, plenty happened. On Tuesday, much of crypto went offline because of a tech issue at AWS, showing how the decentralized economy isn’t always that decentralized. Shaurya Malwa reported the news early. Bitcoin and other major cryptos slipped on bad news for Nvidia, Omkar Godbole reported.
Mantra, a project focused on real world assets, lost 90% of its value. Explanations varied (the company said it was due to “force liquidations” exchanges).
Meanwhile, EigenLayer, a restaking leader, rolled out a “slashing” feature meant to address security concerns (Sam Kessler reported). OKX, a major exchange, announced plans to set up in California following a $500 million settlement with the SEC over claims it operated previously in the U.S. without a money transmitter license. Cheyenne Ligon had that story.
In less good news, Kraken laid off “hundreds” of staff ahead of an expected IPO. And Coinbase became embroiled in a “front running controversy” linked to a curiously named token on its Base L2. Privacy advocates reacted with alarm to rumors that Binance was about to delist Zcash following a long decline in the value of privacy coins.
In D.C. news, Jesse Hamilton reported on a new wave of crypto lobbyists flooding the capital. Some asked if there are now too many trade groups and whether they really all could be effective.
Friends With Benefits, a buzzy social club for creative technologists, launched a new program to build Web3 products for music, film, publishing and other fun activities. (I wrote that one.)
Of course, there was plenty happening in the economy and markets (Trump’s disgust for Fed chair Powell fed into the unease). But, in crypto, it was pretty much business as usual. Fortunes won, fortunes lost, fortunes deferred.
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