CAT CATERPILLAR INC Insider Trading

CAT Group President Johnson Denise C filed 10 separate sales totaling 12,605 shares for $11.4M on 2026-05-14, reducing holdings from 62.4K to 49.8K shares.

Johnson Denise C, Group President at Caterpillar Inc, executed 10 separate sales on 2026-05-14 totaling 12,605 shares for $11,444,169.60, with individual transaction prices ranging from $196.70 to $911.92 per share. At the time of the filing, CAT was trading at $888.31 — approximately -4.6% from its 52-week high of $931.35 — and had posted a 30-day change of +15.3% and a 90-day change of +14.7%. Her 5 prior same-ticker sales at CAT (all on 2026-02-02) were each followed by positive 90-day returns ranging from +30.5% to +31.1%, reflecting a 0-of-5 well-timed rate at the 90-day mark for CAT-specific trades. Her cross-ticker track record similarly shows a 90-day well-timed rate of 0.00% across 8 prior sells, meaning the stock has historically risen after her sales rather than declined.

Caterpillar Group President Denise Johnson sells 6.2K shares for $5.6M as stock rallies +15.2% in 30 days

Johnson Denise C divested 6,196 shares at $914.61 in two transactions, generating $5,637,081.16. Her post-transaction holdings remain substantial at 49,825 shares, indicating continued material equity stake in the company. While the sale timing coincides with a strong recent rally (30-day change: +15.2%, 90-day change: +18.1%), Johnson's historical track record shows poor sell timing—her prior 8 sales had a 0.00% well-timed rate with an average 90-day return of +30.5%, suggesting she tends to exit before further gains. The current sale follows a similar pattern: she may be taking profits near the 52-week high ($931.35 vs. current $914.61), though past behavior indicates subsequent momentum often continues upward. This modest-size divestiture is modest in relation to her remaining position and does not necessarily signal concern about Caterpillar's fundamentals (P/E: 44.68, annual revenue growth +4.3%, market cap $421.3B).

Group President Fassino exercises stock award and sells nearly all shares on same day, maintaining zero net position.

Anthony Fassino, Group President at Caterpillar, executed a three-part transaction on the same day: exercising nearly 21,400 shares from a stock award, immediately withholding about 5,100 shares for tax obligations, and selling the remaining shares in two separate blocks. The net result is zero change in his overall stake despite the large transaction flow. His prior sales at this company have shown mixed results — over a 90-day horizon, only one of his five previous exits proved well-timed as shares subsequently fell, while four saw the stock rise afterward, indicating inconsistent execution on the sell side. Caterpillar itself is a profitable company with growing revenue, and the stock is trading essentially at its 52-week high, suggesting little margin of safety at current levels. The exercise-and-sell pattern is routine for stock-based compensation vesting, and Fassino's zero net position change suggests no material conviction either way in the company's near-term prospects.

Group President De Lange executes large net-neutral trade: exercises 28k shares, sells 24k total for ~$25.9M near all-time highs.

De Lange, as Group President of Caterpillar, exercised options and immediately sold roughly equivalent share volumes for approximately $25.9 million, executing a net-neutral position—acquiring shares through exercise but divesting similar amounts simultaneously. The timing is notable: the sales occurred with the stock at its 52-week high, following a strong multi-month rally. His historical record in this stock shows mixed outcomes: four of five prior sales saw the stock rise afterward, suggesting poor exit timing on those occasions, though his most recent sale in early February preceded a pullback, indicating at least one well-timed exit. The company remains profitable with growing revenue, trading at an elevated valuation. This transaction pattern—exercise-and-sell in a concentrated window near peak prices—is a common way executives monetize option grants rather than a signal of deep conviction about the stock's direction. While not alarming in isolation, the clustering of sales near all-time highs, combined with his modest success timing previous exits, warrants observation to see whether this reflects a conviction to rebalance, or simply routine option liquidity.

CAT Group President exercises and immediately sells shares, achieving net-zero position change despite rising stock near 52-week highs.

Anthony Fassino, Group President at Caterpillar, exercised stock options and disposed of shares on the same day, resulting in no net change to his shareholding. The transactions totaled approximately $11.1 million in dispositions against $2.6 million in acquisitions, a pattern that merits attention given the stock's position near its 52-week highs and the company's strong profitability. Fassino's prior sales in CAT show mixed timing outcomes — some preceded further gains (suggesting he exited too early), while others preceded declines (well-timed exits). The current transaction occurs as the stock has appreciated substantially over recent months, and the Group President's choice to exercise options only to liquidate the resulting shares on the same trading day—rather than hold or accumulate—suggests a disciplined approach to managing exposure at elevated valuations. For investors, this is a data point worth incorporating alongside the company's solid revenue and earnings profile; the filing itself does not constitute a clear directional signal, but the exercise-and-sell pattern is notably different from a straightforward conviction buy or hold.

CFO Emeritus Bonfield exercises and immediately sells $14.4M in CAT shares near all-time highs, offsetting three option exercises in single-day transaction.

Andrew Bonfield, CFO Emeritus of Caterpillar, executed a complex transaction on May 6, 2026, exercising three separate option grants totaling over 23,000 shares and immediately selling nearly the same volume for approximately $14.4 million—a classic wash that suggests tax or liquidity planning rather than a conviction-driven trade. The timing is noteworthy: the stock trades at all-time highs after a rapid rally, and Bonfield's own track record in CAT shows all five of his prior sales in this stock saw shares rise afterward, meaning none of those exits preceded subsequent declines. This insider has historically demonstrated poor timing on exits from this specific company, and the current sale—executed at peak prices—follows the same pattern. The underlying company remains profitable with solid revenue, though it commands a stretched valuation, and the rapid 30-day appreciation that preceded this transaction appears to have triggered his exit rather than fundamental deterioration providing a rationale to sell.

Caterpillar Group President exercises options, then sells entire position for net zero holdings in same-day trading.

Shurman Rodney Michael, Group President of Caterpillar, exercised stock options on May 5th and immediately sold the entire position in two tranches on the same day, leaving him with no additional holdings. The exercise and simultaneous liquidation netted to zero shares, converting option value into cash. This is his fourth open-market sale in the trailing 36-month window following two prior sales, and notably the most recent prior sale saw the stock recover significantly over a longer timeframe after an initial decline. The timing is notable given Caterpillar's strong near-term momentum—the stock has rallied sharply over the prior month and sits near its 52-week high—though the company itself remains fundamentally sound with positive profitability and ongoing revenue growth. The exercise-and-liquidate pattern is a standard tax or cash-planning structure common among executives, but the repetitive selling cadence (three sales now in recent months) sets this apart from typical option exercises where insiders often retain newly acquired shares to demonstrate confidence.

Group President Jason Kaiser sells $4.98M of CAT stock while accumulating shares via exercises in single-day transaction.

Jason Kaiser, Caterpillar's Group President, executed a complex three-part transaction on the same day: exercising stock options to acquire nearly 10,000 shares while simultaneously selling over 5,600 shares for nearly $5 million. The net effect is a modest increase in his overall position, but the decision to cash out a meaningful portion even while exercising options suggests tactical liquidity management rather than pure conviction about the stock's direction. Caterpillar is a profitable, revenue-growing company, but the transaction pattern—buying through exercises then selling a substantial chunk—is more consistent with portfolio rebalancing than a strong bullish conviction that would drive an executive to hold through accumulation. The stock is trading near its recent highs, which may have provided a natural window for Kaiser to take profits on the exercised shares.

CAT director David MacLennan purchases $219k in shares near recent highs amid strong quarterly momentum

Director David MacLennan purchased shares at a price very close to the market price at filing, representing a small incremental addition to his holdings. The timing is notable because it occurs when Caterpillar is trading just below its recent highs and after a significant rally over recent months—most insider buying clusters happen during pullbacks or weakness, making this less typical. The company itself is profitable and growing, but the stock is trading at an elevated valuation relative to historical norms. MacLennan's modest purchase size suggests this may be routine portfolio activity or a discretionary commitment rather than a conviction-level bet, particularly since he's buying into strength rather than a dislocation. This single director buy, while positive, doesn't constitute a broad insider signal and should be evaluated in the context of whether other Caterpillar insiders are similarly accumulating.