Yesterday Micheal Saylor on X hinted that Strategy has purchased more Bitcoin. This time, however, he did it by adding a joke. In fact, he commented by saying “I buy bitcoin only with money I can’t afford to lose”. It refers to the famous precaution that suggests investing only what one is willing to lose, …
Bitcoin: Buy strategy even at highs


Yesterday Micheal Saylor on X hinted that Strategy has purchased more Bitcoin.
This time, however, he did it by adding a joke.
In fact, he commented by saying “I buy bitcoin only with money I can’t afford to lose”.
It refers to the famous precaution that suggests investing only what one is willing to lose, but saying the exact opposite.
Strategy: gli acquisti di Bitcoin ai massimi
The point is that, despite Strategy already having more than 576,000 BTC in its portfolio, with a value exceeding 63 billion dollars, it is continuing to buy even with prices at their peak.
Before the electoral victory of Donald Trump in November 2024, the highest price ever reached by 1 BTC was about $73,000. With the so-called Trump trend, not only did it rise above $100,000 for the first time last December, but by January of this year, it had already almost reached $110,000.
Last week, thanks to a new surge, it recorded a new all-time high almost at 112,000$, and currently its price is only -2% from those highs.
The latest known purchases by Strategy were made on May 19, at a price not far from the highs, and given what Saylor posted, it is reasonable to expect that they also bought more BTC last week.
Therefore, the company is effectively purchasing Bitcoin at its peak.
A few days ago, the same Micheal Saylor had written:
“If you don’t buy bitcoin when their price is at an all-time high, you are losing money”.
The Bitcoin strategy of Strategy
The strategy of Strategy is summarized in another recent tweet by Saylor:
“The only thing better than Bitcoin is more Bitcoin”.
L’unica cosa migliore di Bitcoin è Più Bitcoin. pic.twitter.com/VHzTif0zXH
— Michael Saylor (@saylor) 24 maggio 2025
Strategy (formerly MicroStrategy) is now in all respects a Bitcoin Treasury Company, whose purpose is to accumulate as many BTC as possible.
In order to achieve this goal, she is willing to invest everything she has in Bitcoin, even at the cost of borrowing money to purchase BTC.
In fact, what Saylor wrote yesterday (“I buy bitcoin only with money I can’t afford to lose”) highlights precisely how the company is borrowing enormous amounts of dollars to purchase Bitcoin. In the event that it is unable to repay those loans, it would have to close due to bankruptcy.
It should not be forgotten, however, that it has been almost 5 years since Strategy started buying Bitcoin, given that it began in August 2020 when the price was just over $10,000.
As of today, in total, he has spent more than 40 billion dollars to purchase Bitcoin, but his 576,000 BTC have a current market value exceeding 63 billion.
The basic hypothesis
Behind this strategy, there seems to be the hypothesis that the value of Bitcoin over time may still increase.
When the price of an asset is at historical highs, it is usually less likely that it can rise further.
However, in reality, the $110,000 was a target expected already in the previous cycle, specifically at the end of 2021, but it did not arrive also and especially due to a particularly strong dollar.
Now, however, not only has the 110,000$ mark been simply reached as it should have been four years ago, but a new speculative bubble, typical of Bitcoin cycles, might start to inflate.
The fact is that every time there have been US presidential elections, since Bitcoin has existed (2009), the following year a large speculative bubble has inflated on its price, also and especially thanks to the weakening of the dollar. The dollar indeed tends to strengthen in the election year and to weaken the following year, and the medium-term trend of Bitcoin’s price is inversely correlated to that of the dollar.
This year the Dollar Index has already significantly weakened, dropping from 110 to less than 99 points, but it could fall further, down to 96 or perhaps even 95 points.
Furthermore, there is also the hypothesis that Trump wants to weaken it even more, perhaps bringing the Dollar Index down to those 90 points that have not been seen since 2021, and in that case, the speculative bubble that could inflate on the price of Bitcoin this year could be colossal.
The Strategy Company
Strategy until last year was called MicroSTrategy, and it dealt with services for companies.
It went public in the distant 1998, in the midst of the dot-com bubble, and after the burst of that bubble, it plummeted to historic lows, where it effectively remained until 2020.
With the purchase of Bitcoin, and the beginning of the great speculative bubble of 2020/2021, it began to recover some of the ground lost in the stock market over the previous 20 years, and with the latest bull run at the end of 2024, it managed to reach new highs, significantly higher than those of 2000.
However, it remains to be seen what will happen when inevitably a true bear-market arrives.

Finley Benson is a tech-savvy writer with a background in blockchain development, Finley explores the latest innovations in Web3, DeFi, and smart contract technologies. His articles blend technical depth with real-world applications.