As the S&P 500 grinds through another volatile year, a handful of stocks have quietly slipped into the basement of the index’s performance tables. Yet in at least one of these laggards, corporate insiders are not heading for the exits, they are writing checks. That divergence between market pessimism and executive conviction is drawing fresh attention from investors hunting for mispriced opportunities.
Insider buying in a beaten-down S&P 500 name stands out even more against a backdrop where many executives are cashing out after a long bull run. When directors and senior leaders choose to increase their exposure instead, they are effectively betting their own money that the market has pushed the stock too far in the wrong direction.
The S&P 500’s laggards are under pressure, but not all insiders are selling
The S&P 500 has delivered solid headline gains this year, but the index’s strength masks a sharp divide between winners and losers. As the third quarter wrapped up, a cluster of companies sat among the 10 worst performers in the benchmark, a list that underscored how far some constituents have fallen even as the broader 500 pushed higher. That kind of dispersion is exactly where insider activity can become a powerful secondary signal, helping investors distinguish between value traps and genuine recovery candidates.
At the same time, corporate leaders across the market have been taking advantage of elevated share prices to lock in gains. Over a recent 60 day stretch, insiders collectively unloaded $25.187 billion in company stock, according to data that tracks these transactions. In that environment, any pocket of sustained insider buying in a struggling S&P 500 constituent looks even more notable, because it runs counter to the prevailing pattern of executives reducing exposure.
CarMax stands out as a laggard where insiders are writing checks
One of the clearest examples of this pattern is CarMax, the used car retailer that has been wrestling with a tougher demand backdrop and shifting consumer behavior. The stock has traded more like a cyclical casualty than a steady retailer, leaving it closer to the laggard camp within the S&P 500 even as other consumer names have recovered. That disconnect between the company’s long term growth story and its short term share price has not gone unnoticed inside the boardroom.
In the roster of All Insider Trades for Carmax, one name in particular jumps off the page. Director Steenrod Mitchell, listed with the title Director and a Holding Value of $1.48M, stepped in with a fresh Purchase earlier in Oct. The record shows that this Oct Purchase totaled $91.1k at a price of $45.57 per share, a move that increased his stake at a time when the market narrative around the stock was anything but enthusiastic. The figures $91, $45.57, $1.48 and $91.1 are not just accounting entries, they are a concrete expression of confidence from someone with a front row seat to the company’s strategy.
Inside the CarMax buying: what the trade data reveals
Looking more closely at the transaction history, the pattern at CarMax is not one of sporadic, symbolic buys, but of meaningful allocations that show up clearly in the official logs. The detailed breakdown of All Trades Buys Sells for the stock lists each Insider, their Relation to the company, the Last Date of activity, the type of Transaction and the Owner Type, along with Shares Traded, Price and Shares Held after the move. Within that framework, the Steenrod Mitchell purchase stands out as a deliberate decision to increase exposure rather than simply reinvest a token amount.
For investors, the specifics matter. A Director committing more than $91.1k at $45.57 per share, on top of an existing Holding Value of $1.48M, signals a willingness to lean into volatility rather than wait for clearer skies. It suggests that from the vantage point of the board, the current valuation does not fully reflect the company’s long term earnings power, even if near term headwinds in used vehicle pricing and financing costs remain. When that kind of conviction appears in the same tape that shows insiders elsewhere unloading $25.187 billion in stock, it becomes a data point that is hard to ignore.
Why insider buying in a laggard can matter more than insider selling
Insider selling often grabs headlines, but it is a blunt instrument as a signal. Executives sell for many reasons that have little to do with their view of the business, from diversification to tax planning. The recent wave of $25.187 billion in sales across corporate America, captured in data compiled by Barchart, illustrates how aggregate selling can spike simply because share prices have risen and executives are rebalancing. In that context, I put more analytical weight on concentrated insider buying, especially when it occurs in a stock that has already been punished.
By contrast, when a Director or senior leader reaches into their own pocket to buy shares on the open market, the motivations tend to be narrower. They are usually either signaling confidence in the company’s trajectory or taking advantage of what they see as a mispricing. The CarMax activity, with Steenrod Mitchell adding to a seven figure Holding Value through a six figure Purchase at a depressed price, fits that profile. It does not guarantee a turnaround, but it tilts the odds that the people closest to the numbers believe the current market verdict is too harsh.
Comparing CarMax to insider trends at other S&P 500 names
To understand how unusual this pattern is, it helps to look at insider behavior at other large companies that have fared better in the index. In the technology and information services space, for example, the ledger of All Insider Trades for Gartner shows a different tilt. There, Rupani Altaf Evp, Chief Information Officer, is recorded with a Holding Value of $125k and an Oct 15, 2025 Sale of $14.4k at a price of $236 per share. Those figures, $236, $125 and $14.4, reflect a classic pattern of executives trimming positions in a stock that has already delivered strong gains.
That contrast is instructive. Where CarMax insiders are adding exposure at lower prices, Gartner’s leadership is monetizing a portion of their holdings at higher levels, consistent with a company that has not been dragged into the S&P 500’s laggard column. It underscores how insider flows often mirror the underlying performance of the stock: buying tends to cluster in names that have fallen out of favor, while selling is more common in those that have already rewarded shareholders. For investors scanning the index for contrarian ideas, the CarMax pattern looks more like a vote of confidence than a routine portfolio adjustment.
Market context: when insider conviction meets shifting sentiment
Insider moves do not occur in a vacuum, they intersect with broader shifts in market sentiment and sector narratives. In high profile growth stories, for instance, share prices can swing sharply on expectations alone, as seen when the company led by Elon Musk saw its stock begin surging after reports suggested the EV giant would beat analyst delivery expectations and after it joined hands with President Trump on policy discussions. That surge helped put Elon Musk back atop the billionaires list as the company almost recovered lost wealth, a reminder of how quickly sentiment can flip when investors believe a story is back on track, as detailed in coverage of how the company’s stock began surging.
For a more prosaic business like CarMax, the catalysts are different, but the mechanism is similar. If the market begins to believe that used vehicle margins are stabilizing, that financing conditions are easing, or that the company’s omnichannel investments are starting to pay off, sentiment can move faster than fundamentals. In that kind of environment, insider buying at depressed levels can act as a bridge between today’s skepticism and tomorrow’s potential re-rating, especially when it is occurring while other executives across the market are busy cashing out.
How investors can read the signal in CarMax’s insider activity
For portfolio managers and individual investors alike, the key is not to treat insider buying as a magic bullet, but as one input in a broader mosaic of information. In the case of CarMax, the combination of S&P 500 laggard status, a challenging macro backdrop and a Director like Steenrod Mitchell increasing a $1.48M Holding Value through a $91.1k Purchase at $45.57 per share is a meaningful data point. It suggests that at least some insiders see more upside than downside from current levels, even if the path back to favor in the index is uneven.
In my view, the most productive way to use that information is to pair it with a hard look at the company’s balance sheet, competitive position and earnings trajectory. If those fundamentals line up with the story the insiders appear to be telling with their own money, then the stock may warrant a closer look as a contrarian addition in a diversified portfolio. In a year when the S&P 500’s headline gains have masked deep underperformance in parts of the index, following the dollars of insiders who are buying, not selling, can help investors separate the merely cheap from the genuinely mispriced.
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Grant Mercer covers market dynamics, business trends, and the economic forces driving growth across industries. His analysis connects macro movements with real-world implications for investors, entrepreneurs, and professionals. Through his work at The Daily Overview, Grant helps readers understand how markets function and where opportunities may emerge.
