Bitcoin’s Q2 Playbook: ‘Digital Capitalist’ Drops Contrarian Bet for Hedge Funds Chasing Alpha

Wall Street’s latest crypto whisper? A self-proclaimed ’Digital Capitalist’ just leaked a high-conviction Bitcoin trade—right as institutional portfolios scramble for Q2 positioning.
The Pitch:
Forget ’safe’ ETFs. This play targets overlooked miners and derivative instruments, leveraging Bitcoin’s post-halving supply crunch. One hedge fund PM grumbled, ’It’s either genius or a great way to lose your 3rd vacation home.’
The Catch:
The tip hinges on Fed rate cuts materializing by August. Because nothing screams ’asymmetric risk’ like betting on both macro and crypto volatility—while Wall Street still pretends to understand both.
Strategy Could Soon Join S&P 500
Walton wrote in a post on the X app:
Q2 is likely going to be the big blow out quarter on Earnings for $MSTR
The quarter ends on 6/30 (52 days from now)
The earnings release call will likely be on August 5th / 6th
Technically Qualifying $MSTR for the S&P500
The market will react surprised & bewildered…
— Jeff Walton (@PunterJeff) May 9, 2025
The S&P 500 is the US stock market benchmark comprised of the 500 largest companies in the United States by total market capitalization. Strategy’s entry onto the index WOULD likely cause its share prices to soar.
That’s what happened this week after markets slated Coinbase, the largest US cryptocurrency exchange, to join the S&P 500 with a market cap north of $67 billion.
Did Michael Saylor lead the Company to Join Coinbase?
Coinbase will enter the broad stock benchmark because Capital One Financial will acquire Discover Financial Services, bumping it off the stock exchanges. After that headline broke, COIN shares flew from under $200 to $266 to close the week.
That was an easy 33% gain for shareholders like Ark Invest’s Cathie Wood. The investing maven is very bullish on crypto assets and Coinbase stocks. COIN is the third-largest holding in the ARKK ETF.
Walton says Strategy could deliver a similar performance in August if it makes it onto the index.
The bitcoin treasury company guarantees returns on BTC investments to its clients with fixed return corporate bonds that retain the option to convert these notes into Strategy stocks.
The company’s founder, MIT graduate Michael Saylor, innovated this strategy to spectacular effect. In April, its stock’s 1-year return on investment surpassed Jim Cramer’s “Magnificent Seven” for market returns.
In a more recent update, Saylor informed that MSTR is winning the “financial triple crown” due to its Bitcoin-based strategy.
$MSTR is winning the Financial Triple Crown:
1st place this quarter
1st place this year
1st place since adopting the Bitcoin Standard
Our @Strategy works because it’s built on $BTC. pic.twitter.com/Leq9LQ6lCq
— Michael Saylor (@saylor) May 17, 2025