President Trump's independent third-party money managers have been busy over the past year and a half, executing around 21,000 trades last year and more than 1,000 in June 2026.
Two of the three largest purchases are financial service powerhouses with sustainable moats.
Additionally, Trump's investment team plowed seven figures into a services company that announced a game-changing acquisition in March.
Some of Wall Street's savviest billionaire money managers oversee hundreds of trades per quarter. But in terms of sheer volume, these billionaires can't hold a candle to President Donald Trump's independent third-party money managers. According to data from the U.S. Office of Government Ethics (OGE), Trump's investment team placed in the neighborhood of 21,000 trades on the president's behalf in 2025.
The latest OGE financial disclosure for President Trump, filed in August, shows that north of 1,000 trades were completed in June 2026. Although the White House has stated that Trump and his family play no role in executing these trades, the newest financial disclosure reveals that between $1 million and $5 million was spent buying shares of Visa (NYSE: V), Mastercard (NYSE: MA), and Cintas (NASDAQ: CTAS) in June.
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President Trump's independent third-party money managers were busy in June. Image source: Official White House Photo by Molly Riley.
Few publicly traded companies have been steadier buy-and-hold candidates since the financial crisis than payment facilitators Visa and Mastercard. Including dividends, Visa and Mastercard have returned 1,810% and 2,380%, respectively, since the start of 2010.
Gains of this magnitude don't occur by accident. They reflect Visa's and Mastercard's position as the United States' No. 1 and No. 2 payment processors by credit card network purchase volume. No other payment processors are particularly close to rivaling their share.
BREAKING: President Trump's financial disclosure report for the most recent period was just released.
-- TrendSpider (@TrendSpider) August 22, 2026
Here is every stock / ETF he spent more than $1,000,000 buying in June:
-Berkshire Hathaway $BRK.B
-Cintas Corp $CTAS
-Visa $V
-Mastercard $MA
-International Treasury Bond... pic.twitter.com/XW3Rj82rkG
Something else that's helped set Visa and Mastercard apart is the unwillingness of their respective management teams to move into lending. While some of their peers, such as American Express, can effectively double-dip and generate profits as payment networks and lenders (via credit cards), Visa and Mastercard have stuck solely to electronic payment facilitation.
The advantage of the latter is that Visa and Mastercard aren't required to set aside capital during challenging times to cover potential delinquencies and loan losses. This enables both companies to bounce back from recessions considerably faster than many of their peers.
Image source: Getty Images.
Perhaps the bigger surprise is corporate identity uniform and business services provider Cintas being among Donald Trump's largest purchases in June. Including dividends, shares of Cintas have soared by more than 85,000% since its August 1983 initial public offering (IPO).
Cintas is effectively linked at the hip to the health of the U.S. economy. If the economy is growing and jobs are being created at a steady pace, there's a good likelihood that businesses will need uniforms, towels, mats, safety products, and so on. In short, Cintas directly benefits from economic expansions lasting disproportionately longer than recessions.
The outsize gains Cintas has enjoyed since its IPO also reflect management's appetite for acquisitions. Although most of the company's purchases have been of the bolt-on variety (i.e., designed to enhance existing operations or expand into a niche new product line), its March-announced cash and stock acquisition of UniFirst for $5.5 billion is a potential game changer.
If this combination, set to close later this year, gets the green light from regulators, it would expand Cintas's reach to approximately 1.5 million businesses in North America and result in substantial cost synergies.
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American Express is an advertising partner of Motley Fool Money. Sean Williams has positions in Mastercard and Visa. The Motley Fool has positions in and recommends American Express, Mastercard, and Visa. The Motley Fool recommends Cintas. The Motley Fool has a disclosure policy.