MicroStrategy, fronted by outspoken Bitcoin bull and Executive Chairman Michael Saylor, added to its sizable Bitcoin holdings Monday with the purchase of 55,500 BTC—or $5.4 billion worth.

The purchase is the latest—and largest—in a string of Bitcoin purchases dating back to 2020, when MicroStrategy and Saylor made the strategic decision to allocate capital to the leading cryptocurrency to “maximize long-term value for shareholders.”

Since that time, the business intelligence firm has reshaped itself into a Bitcoin development company and pioneered the crypto treasury reserve asset model that others have copied. It has also amassed 386,700 Bitcoin as of this writing, making it the largest corporate treasury reserve holder of the asset. That’s more than $36 billion worth, as of this writing.

Here’s a look back at MicroStrategy’s five largest BTC purchases to date and their immediate impacts on the price of Bitcoin, marked from the time of Saylor’s announcements via social media.

#1) 55,500 BTC - November 25, 2024

Average Price: $97,862 
Total Spend: $5.4 billion 

Michael Saylor announced MicroStrategy’s largest ever purchase of Bitcoin, by both BTC and USD denominations, on November 25. The purchase of 55,500 Bitcoin surpassed its previous top acquisition by more than $800 million.

In the hours after the Saylor announcement, Bitcoin dropped by about $4,000 to under $94,000, a 4% decrease from the average price paid by MicroStrategy.

The latest and largest purchase by MicroStrategy (as of this writing) brings the company’s holdings to over $36 billion.

2) 51,780 BTC - Nov. 18, 2024

Average price: $88,627
Total spend: $4.6 billion 

The second largest Bitcoin purchase in MicroStrategy history came just one week before its largest-ever purchase. Though Bitcoin dropped shortly in the hour following the announcement, a rebound followed and it reached a daily high of $92,653, just 2% shy of its all-time high price (set last week) according to data from CoinGecko.

The following day, Bitcoin hit a new all-time high price above $94,000. MicroStrategy’s latest purchase brought its holdings to 331,200 BTC.

3) 29,646 BTC - Dec. 21, 2020

Average price: $21,925
Total spend: $650 million

MicroStrategy’s second-largest Bitcoin purchase took place in December 2020 amid rising Bitcoin prices and bull market sentiment. The firm disclosed a purchase of 29,645 BTC for its fourth-ever Bitcoin acquisition.

Despite the purchase being the largest for MicroStrategy at the time, Bitcoin price's was relatively unchanged in the 24 hours around the announcement. Data from CoinGecko showcases a Bitcoin open price of $23,518 on December 21, closing one day later at $23,795 for a negligible gain.

4) 27,200 BTC - Nov. 11, 2024

Average price: $74,463
Total spend: $2.03 billion

Less than one week after Donald Trump was named President-elect, MicroStrategy announced a purchase of 27,200 Bitcoin. That stash was purchased during the timeframe of October 31 to November 10, a time in which Bitcoin ranged in price from $72,000 to $80,000.

However, following the Saylor announcement on the morning of November 11, Bitcoin moved violently upwards, closing the day at $88,637—a move of more than 10%—after setting yet another new all-time high price after the election.

5) 21,454 BTC - Aug. 11, 2020

Average price: $11,652
Total spend: $250 million 

MicroStrategy’s fourth-largest Bitcoin purchase of all-time was its first-ever purchase and its lowest recorded average price.

On the back of social restrictions and macroeconomic shocks from the COVID-19 pandemic, Saylor rationalized the company’s purchase saying, “Our decision to invest in Bitcoin at this time was driven in part by a confluence of macro factors affecting the economic and business landscape that we believe is creating long-term risks for our corporate treasury program—risks that should be addressed proactively.”

While the purchase has aged well, now up nearly 700% at today’s Bitcoin price, the initial announcement meant little for Bitcoin’s price in the immediate aftermath. Bitcoin opened August 11, 2020 at $11,682 and closed the following day at $11,579—a negligible decline.

Edited by Andrew Hayward

Editor's note: This story was originally published on November 19, 2024 and last updated with new details on November 25.