Why Dave Portnoy Is Begging Michael Saylor to Buy More Bitcoin

Cover image via youtu.be Disclaimer: The opinions expressed by our writers are their own and do not represent the views of U.Today. The financial and market information provided on U.Today is intended for informational purposes only. U.Today is not liable for any financial losses incurred while trading cryptocurrencies. Conduct your own research by contacting financial experts before making any investment decisions. We believe that all content is accurate as of the date of publication, but certain offers mentioned may no longer be available. Barstool Sports founder Dave Portnoy called on Michael Saylor, the head of the largest Bitcoin treasury company, MicroStrategy, to increase the scale of the company's Bitcoin purchases, posting the meme "MORE!" as a reaction to the official announcement that MicroStrategy had acquired 1,550 BTC more over the past week. Advertisement Portnoy's post coincided with his own admission last week that he lacked free cash to continue supporting his portfolio on his own amid the prolonged market decline. https://t.co/2v5dcNqFav pic.twitter.com/qqliu2QtKJ — Dave Portnoy (@stoolpresidente) June 8, 2026 For Dave Portnoy, who compared the current situation on exchanges to chaos at a racetrack, large institutional deals remain the main factor behind a possible recovery of his positions. Advertisement His relationship with crypto, which the businessman himself described as an attempt to mix water with oil, has led to his capital being locked in losing positions, while his net losses, including positions in Bitcoin and XRP , already amount to millions of dollars. HOT Stories XRP, Bitcoin (BTC), Ethereum (ETH) and Hyperliquid (HYPE) Price Analysis for June 8: Are Top-Tier Assets Ready to Bounce? Schiff: 99% Crash Wouldn't Phase Bitcoin 'Cult' Dave Portnoy is down millions on XRP, BTC, and MSTR On the spot market, Portnoy's large Bitcoin position remains under strong pressure as the price fluctuates around $63,000. The situation is worsened by his XRP purchase, made in late January near the local peak of about $1.70, while the asset is currently trading around $1.17. Moreover, his attempt to diversify the portfolio by buying MSTR shares a week ago led to that position falling by another 20%, according to the businessman himself. Portnoy thus confirmed that he had fully exhausted his free liquidity during the intermediate stages of the market decline and had lost the ability to defend his assets. Advertisement You Might Also Like Mon, 06/08/2026 - 14:41 Michael Saylor Boosts Bitcoin Reserve With $101 Million BTC Purchase By Caroline Amosun MicroStrategy's purchase of 1,550 BTC was made at an average price of $65,332 amid the broader market decline. This move became an important signal for industry participants, as one week earlier the company, which holds more than 800,000 BTC, broke its "never sell" rule for the first time in three years. Yes, the earlier sale of 32 BTC to pay dividends triggered a wave of panic and accelerated the decline in prices, but the new purchase exceeded the size of that sale by almost 50 times. Interestingly, despite the general pessimism, Dave Portnoy also announced at the time that he intended to hold his positions without realizing losses. The main psychological reference point for Portnoy, according to him, remains the long-standing personal promise of former Twitter CEO Jack Dorsey that Bitcoin will inevitably reach $1 million. #Dave Portnoy #Bitcoin #XRP #Michael Saylor #Bitcoin News