Strategy, the company chaired by Michael Saylor, is reportedly preparing its first repurchase of convertible bonds in a bid to lower balance-sheet risk tied to its Bitcoin-heavy strategy. Market reports say Strategy intends to buy back $1.5 billion of convertible notes due in 2029 for about $1.38 billion, offering bondholders early liquidity at a discount. The move is viewed as an attempt to rein in leverage and reduce the chance of future funding stress. Commentators have linked the plan to Saylor's recent remarks that "Bitcoin sales could be considered if necessary to optimize the debt structure." Strategy's multi-year BTC accumulation has made it one of the largest institutional Bitcoin holders, while leaving it more exposed to market swings because of its debt load. Analysts outline three broad outcomes if the company did not pursue a buyback: 1) Bull-case into 2029: If Bitcoin rallies strongly and Strategy's shares trade above the conversion price, bondholders could convert into equity. Strategy would effectively retire the debt without a cash outlay, but existing shareholders would face meaningful dilution from new share issuance. 2) Sideways BTC, weak equity: If Bitcoin stagnates and the stock underperforms, investors may seek cash repayment. That could draw down limited cash resources and raise the prospect of selling Bitcoin, adding potential pressure to the market. 3) Bear-market stress: If Bitcoin drops sharply and the stock trades well below the conversion level, bondholders would likely demand cash directly. With refinancing harder to obtain, Strategy could be forced to liquidate part of its Bitcoin holdings, intensifying financial strain. Against that backdrop, the reported buyback is seen as using the current Bitcoin recovery window to reduce uncertainty sooner rather than later. Still, the approach fuels debate about liquidity. If repurchases continue, some argue the firm's cash balance could prove insufficient, increasing the likelihood of partial BTC sales over time. Market observers say Strategy's key question is whether it is safer to trim BTC in an orderly way now, or risk being forced into sales under weaker market conditions later. This is not investment advice. Related news: A denial has come from the country alleged to have sold $1 billion worth of Bitcoin: "We don't recall anything like that." Continue reading: Will Michael Saylor and Strategy Sell Bitcoin Soon? New Claims and Information Have Emerged

Whale Alert: The wallet linked to Morgan Stanley's bitcoin fund has received more than 467 BTC (bitcoin:native) from Coinbase Prime over the past four days.

WHALE reported that a wallet linked to a Morgan Stanley Bitcoin fund has received more than 467 BTC from Coinbase Prime over the past four days.

CoinDesk reports that Friday marks the deadline for institutional investment managers to file first-quarter holdings disclosures with the U.S. Securities and Exchange Commission, offering a window into how sovereign funds, universities and banks are positioning in crypto ETFs. Abu Dhabi's sovereign wealth fund Mubadala boosted its exposure to BlackRock's iShares Bitcoin Trust ETF (IBIT). As of March 31, its stake rose to 14,721,917 shares from 12,702,323, worth nearly $660 million at current prices. Mubadala subsidiary Abu Dhabi Investment Committee (ADIC) reported an unchanged IBIT position of 8,218,712 shares valued at $315.8 million as of March 31, the same share count previously reported by another subsidiary, Al Warda Investments, at year-end. The roughly $92 million value drop was attributed to IBIT's quarterly price decline rather than sales. The filing also shifted which entity reports the position: after Al Warda filed independently for three quarters, the company said Friday that the holdings will now be reported through ADIC, with the beneficial owner unchanged. University endowments largely held steady. Dartmouth College reported 201,531 IBIT shares worth just over $9 million, unchanged from the prior quarter. Dartmouth also rotated its ether ETF exposure, moving from the Grayscale Ethereum Mini Trust to Grayscale's Ethereum Staking ETF while keeping a 178,148-share position, and disclosed a new stake of 304,803 shares in the Bitwise Solana Staking ETF valued at nearly $3.67 million. The move is among early signs that institutional endowments are exploring allocations beyond Bitcoin (BTC) and Ethereum (ETH). Brown University maintained 212,500 IBIT shares. Emory University streamlined its bitcoin ETF exposure, selling its entire 4,450-share IBIT position and increasing its stake in the Grayscale Bitcoin Mini Trust to 1,354,148 shares from slightly more than 1 million. Harvard University, which drew attention in late 2025 after revealing a large IBIT position, continued to cut back in the first quarter. Its endowment reportedly held 3,044,612 IBIT shares as of March 31, valued around $117 million, down 43% from 5.35 million shares at the end of 2025, following a 21% reduction in the fourth quarter. Harvard also fully liquidated its $86.8 million position in BlackRock's spot Ethereum ETF, which launched just last quarter. IBIT is no longer Harvard's largest disclosed holding; TSMC now tops its 13F portfolio, while Alphabet, Microsoft and the SPDR Gold Trust also rank above TSMC. Banks and brokers also adjusted exposures and hedges. Royal Bank of Canada increased its direct IBIT holdings and expanded its use of put and call options. Scotiabank, after exiting prior holdings in U.S. bitcoin stocks tied to Trump, added 214,370 IBIT shares. Barclays reported a layered IBIT footprint, including about 4.46 million shares of the spot ETF alongside sizable put and call option positions. Some investors reduced risk after crypto-market weakness in the first quarter. Hong Kong's Laurore, an offshore entity that surfaced earlier this year as one of the largest IBIT holders, cut its stake to 6,846,279 shares from 8,786,279, according to filings.

Claims that Bhutan's state-backed investment firm, Druk Holding and Investments (DHI), has been selling Bitcoin have triggered scrutiny after officials offered limited clarification. Onchain tracking by Arkham Intelligence suggests that about $1 billion in Bitcoin has been withdrawn since July 2025 from wallets Arkham attributes to Bhutan, while DHI management said it does not recall making any sales. Bhutan, a Himalayan nation, is widely viewed as the second country after El Salvador to officially mine Bitcoin and hold it as reserves. Arkham's data also indicates that roughly $207 million worth of BTC has been transferred so far this year from wallets believed to belong to DHI to exchanges and trading firms. Arkham estimates Bhutan-linked wallets held about 13,000 BTC in October 2024, falling to around 3,100 BTC as of Friday. If that pace continues, Arkham projects Bhutan could have sold all of its Bitcoin by October 2026. DHI CEO Ujjwal Deep Dahal said, "I don't remember the last time we sold BTC." Asked about the wallet activity flagged by Arkham, the firm added only: "Our statement remains valid; we have nothing further to add." Bhutan has not directly challenged Arkham's wallet attribution, but it has not disclosed how much Bitcoin it holds. Arkham says Bhutan has been mining Bitcoin since at least 2019 and that the government finances at least four mining facilities. Its analysts noted that transfers to centralized exchanges or OTC trading firms typically signal intent to sell, but added that onchain data cannot conclusively prove sales because exchange order books are not visible onchain. A source familiar with one trading firm that buys BTC from Bhutan-linked wallets said there have been no recent sales, raising the possibility that the transfers reflect custody movements, collateral or credit activity, or OTC transactions rather than direct spot selling. In December, Bhutan's government said it would allocate up to 10,000 BTC to support development of Gelephu Mindfulness City, a planned economic zone in the country's south. The pledge, valued at about $860 million at the time, appears difficult to reconcile with the smaller holdings implied by current onchain estimates. Dahal also said unusually steady rainfall this year has boosted hydropower generation, keeping mining operations active. He added that Bhutan's mining runs on renewable energy and that the country is upgrading to next-generation equipment to stay competitive. This is not investment advice.

All 12 US spot Bitcoin ETFs reported net outflows on May 15, with total redemptions reaching $290 million, according to SoSoValue data. The absence of any inflow was notable amid this year's uneven institutional demand. Spot Ethereum ETFs also stayed under pressure, posting $65.65 million in net outflows and extending their withdrawal streak to five consecutive sessions, taking total losses for the run into the hundreds of millions. The broad selling contrasts with strength elsewhere in crypto. SUI jumped 18% to $1.24 on institutional staking momentum and a major fintech integration, while TON, SIREN, and VVV delivered double-digit gains over the past week. The split points to rotation rather than a wholesale exit from digital assets, with flows shifting away from passive, broad-based bitcoin and ether exposure toward higher-beta tokens and targeted ecosystem themes. Regulatory uncertainty is also weighing on sentiment. A major US crypto bill has faced renewed pushback from banking interests ahead of a Senate vote, reviving concerns of a policy stall. With banks attempting to block the legislation, institutions may be staying cautious, as ETF flows have historically been sensitive to regulatory headlines. Even as spot crypto ETFs lose momentum, institutional activity is increasingly showing up in tokenized real-world assets (RWA). Over the past week, the on-chain RWA market exceeded $20 billion, Bullish announced a $4.2 billion acquisition, and Ondo completed its first live settlement with JPMorgan. The contrast suggests large investors are prioritizing yield-bearing, regulated structures closer to traditional finance over pure spot beta. The current drawdowns in bitcoin and ether ETFs may reflect tactical repositioning toward areas offering clearer regulation, deeper liquidity, and more predictable cash flows. Whether the outflow streak proves temporary remains unclear. Upcoming US inflation data and any progress on the Senate crypto bill could quickly shift sentiment. For now, the latest session stands out: every US spot Bitcoin ETF finished the day as a net outflow.

Bitcoin slid 3.2% to about $78,000 during Asian trading on Saturday, reversing last week's rally. Data from CoinGlass showed roughly $581 million in liquidations over the past 24 hours, with about 95% tied to long positions. Major altcoins also weakened: Solana fell 5%, XRP dropped 4.3%, and Ether declined 3.3%.

May 16 — Coinglass data show that as Bitcoin weakened and briefly slipped below $78,000, funding rates on leading centralized and decentralized exchanges have moved deeper into bearish territory, underscoring growing downside sentiment, according to BlockBeats. BlockBeats explanation: A funding rate is a periodic fee used in perpetual futures to keep contract prices aligned with the underlying spot market. It is exchanged between long and short traders rather than collected by the platform, and it adjusts the cost or return of holding positions so prices stay close to the underlying asset. A 0.01% funding rate is considered the baseline. Readings above 0.01% typically signal a broadly bullish market, while levels below 0.005% generally indicate bearish conditions.