CarMax President and CEO Keith Barr bought 9,400 shares on the open market at $53.01 per share on June 22, 2026, spending about $498,250. Open-market buying by a CEO is notable because it involves the executive using personal funds to increase exposure to the company’s stock, rather than receiving shares through compensation or exercising options. Barr’s role matters: as the top executive, he is closely tied to CarMax’s strategy, operating performance, and capital allocation decisions. While insiders can’t trade on nonpublic information, investors often watch CEO purchases because they can reflect management’s view of the business relative to the current share price. The absence of a pre-scheduled 10b5-1 trading plan can make the timing appear more discretionary, though it does not, by itself, confirm motive. This purchase also came alongside another insider buy the same day: Peter J. Bensen purchased roughly $130,500 of CarMax stock. Two insider purchases within 30 days, including a larger buy from the CEO, stands out as a cluster of buying activity and may draw additional attention from investors monitoring insider sentiment.