Will CEO Jim Conroy make any discretionary stock sale by December 31, 2026?
Current Prediction
Why This Question Matters
CEO Conroy's 100% retention of discretionary shares is the strongest individual insider signal. With the stock near all-time highs and one year of data, any discretionary sale would be the first break in the pattern and would weaken the governance alignment assessment from ALIGNED. This tests whether the retention signal was genuine long-term conviction or constrained by timing and optics in a new CEO's first year.
Prediction Distribution
Individual Predictions(9 runs)
CEO Conroy retained 100% of discretionary shares in his first year with zero sales beyond tax withholding. However, the 9-month forward window (April-December 2026) is substantial. The CFO Form 144 filing on 3/26 for 4,883 shares signals C-suite selling norms may be shifting. Critically, the resolution criteria exclude 10b5-1 pre-planned sales -- the most common institutional CEO selling mechanism. If Conroy establishes a 10b5-1 plan, those sales would NOT trigger resolution, significantly narrowing the YES scenarios.
The resolution criteria are narrowly drawn: only discretionary sales count -- not tax withholding, gifts, or 10b5-1 pre-planned sales. Most institutional CEO selling at mature retailers happens through 10b5-1 plans, which are explicitly excluded. Conroy demonstrated 100% retention across 76,041 shares acquired with only 8,268 withheld for taxes. The cliff-vesting on 21,140 annual grant shares until 2030 structurally limits available shares. Raw discretionary sales by sitting CEOs at S&P 500 companies are uncommon relative to planned programs.
I weight the 9-month time horizon more heavily. While Conroy first-year retention is notable, the committee flagged it as EXPECTED behavior for new CEOs -- not extraordinary conviction. Several dynamics push probability higher: PRSU tranches will vest creating new disposable shares, personal financial advisors will recommend diversification as equity position grows ($14.4M+), CFO Form 144 suggests compliance infrastructure is in place, and by late 2026 the honeymoon retention social norm weakens. However, the 10b5-1 exclusion substantially reduces YES probability.
Conroy has shown zero discretionary sales across his first year, retaining 100% of non-tax-withheld shares. The resolution criteria exclusion of 10b5-1 pre-planned sales is the key analytical factor -- this is the most common institutional approach for CEO diversification. Over 9 months, the probability of a raw discretionary sale (not pre-planned) is moderate but not high. Mid-level officers selling 5-8% is routine post-vesting behavior and does not predict CEO behavior. If Conroy wants to sell, his legal team would almost certainly recommend a 10b5-1 plan.
Base rate for S&P 500 CEOs in their second year making discretionary (non-10b5-1) sales in a 9-month window is approximately 20-30%. Conroy first-year retention is positive but the committee notes it is expected new-CEO behavior. PRSU vesting creates opportunities -- the next tranche of ~16,470 shares will vest. However, the 10b5-1 exclusion substantially reduces effective probability because sophisticated CEOs with legal counsel use pre-planned programs. The CFO Form 144 is marginal upward pressure. Overall moderately below base rate.
Anchoring on the resolution criteria exclusion of 10b5-1 plans. In modern corporate governance, discretionary ad-hoc sales by sitting CEOs are uncommon -- they create legal exposure, media scrutiny, and board friction. The standard practice is to establish a Rule 10b5-1 plan during an open trading window. If Conroy decides to diversify, the overwhelmingly likely mechanism is a 10b5-1 plan which would NOT trigger this market. The only YES scenarios: impulsive or poorly-advised ad-hoc sale, rapid departure, or personal liquidity event -- none likely for a well-compensated S&P 500 CEO.
Zero discretionary sales in year one. 10b5-1 plans excluded from resolution criteria -- this is the key constraint. Most CEO selling goes through 10b5-1 plans. CFO Form 144 is a minor concern. Stock at ATH creates some pressure. 9-month window is meaningful. But combination of first-year retention plus 10b5-1 exclusion keeps probability low.
9-month window is long. CEO retained all shares so far but that is expected for year one. PRSU vestings will create new sellable shares. CFO already filed Form 144. The 10b5-1 exclusion is important -- if Conroy sets up a plan, those sales do not count. Slightly above pure base rate due to limited data window and growing equity position creating diversification pressure.
Strong retention signal: 67,773 net shares added with zero discretionary sales. 10b5-1 exclusion is the most important factor -- sophisticated CEOs use pre-planned programs. Even with 9 months of exposure, probability of ad-hoc discretionary sale is low for a well-advised S&P 500 CEO. CFO Form 144 is noise for predicting CEO behavior.
Resolution Criteria
Resolves YES if any Form 4 filing for CEO James Conroy reports a disposition coded as a discretionary sale (not tax withholding, not gift, not 10b5-1 pre-planned) between April 1, 2026 and December 31, 2026. Resolves NO if all dispositions are tax withholding, gifts, or no dispositions occur.
Resolution Source
SEC EDGAR Form 4 filings for James Conroy, Ross Stores Inc.
Source Trigger
CEO Conroy discretionary share sales at any price level
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