undamentalytics Newsletter

Stilwell Associates, L.P.: insider trades

Director at 2 companies we cover. 17 open-market purchases and 3 sales not made under a pre-set plan, reported from September 17, 2018 to December 17, 2025.

Would copying Stilwell Associates, L.P.’s purchases have beaten the S&P 500?

Too few purchases to judge. Only 8 purchases have 12 months of prices after the report; we judge insiders once they have 20. The figures below can swing a long way on a handful of trades. Buying each purchase the day after it was reported, an equal amount each, and holding it 12 months or until they reported a sale would have turned $10,000 on November 23, 2021 into $19,895 by November 2, 2026, +15.0% a year. The copy held shares only 26% of the time, so the fair comparison is the S&P 500 on those same days with Treasury bills otherwise: $10,208, +0.4% a year (the S&P 500 held throughout made $17,275, +11.8% a year). Beta against the index was 0.09. Twelve months after each report, the average purchase was +57.3% against the S&P 500 (median +54.5%), and 100% beat it. Measured from the trade date, the insider’s own timing, the average was +56.9%. After their sales, the shares moved −41.7% against the index over 12 months on average (a negative figure means selling was the right call); 100% trailed it.

With 296 insiders tested, some will look skilled or unskilled by chance alone: when we replaced each insider’s stocks with random companies bought on the same days, about 5.7 cleared the bar ahead and 23.3 behind. One record on its own proves little.

$0$10.0k$20.0k 202120222023202420252026 $19.9k$17.3k$10.2k
Copying Stilwell Associates, L.P.S&P 500, same days investedS&P 500, held throughout $10,000 copying Stilwell Associates, L.P.’s open-market purchases from November 23, 2021, before costs and taxes, marked weekly. Each purchase gets the same starting stake, bought at the close of the first trading day after the report and sold 12 months later or the day after a reported sale of that stock; uninvested money earns the Treasury bill rate. “Same days invested” holds the S&P 500 only on the days the copy held shares, Treasury bills otherwise.
Return a year, copying
+15.0%
S&P 500, same days invested
+0.4% (held throughout +11.8%)
Time in shares
26%
Sharpe ratio (S&P 500)
0.65 (0.50)
Biggest drop (S&P 500)
−25% (−25%)
Market sensitivity (beta)
0.09
Purchases copied
8

Trade by trade

Stilwell Associates, L.P.: trades against the S&P 500 afterwards
MeasuredTrades countedAverage vs S&P 500MedianWent the right wayYearst-statisticp-valueEvidence
Purchases, 3 months after the report 8 +13.7% +8.7% 100% 2 — — Not enough years
Purchases, 6 months after the report 8 +29.5% +27.5% 100% 2 — — Not enough years
Purchases, 12 months after the report 8 +57.3% +54.5% 100% 2 — — Not enough years
Purchases, 12 months after the trade 8 +56.9% +56.3% 100% 2 — — Not enough years
Sales, 3 months after the report 3 −16.1% −16.4% 100% 2 — — Not enough years
Sales, 12 months after the report 2 −41.7% −41.7% 100% 2 — — Not enough years
Sales, 12 months after the trade 2 −45.5% −45.5% 100% 2 — — Not enough years

“Average vs S&P 500” is the stock’s return including dividends minus the index’s over the same dates, from the close on the first trading day after the report, or from the close on the trade date. Only windows that have finished are counted. For sales, a negative figure means the stock lagged after it was sold, so selling was the right call (green). “Went the right way” is the share of purchases that beat the index, or of sales that trailed it. The t-statistic uses one average per year of reports, because one person’s trades bunch into the same stock and weeks, and needs trades in at least four different years; the p-value comes from the t distribution with that number of years (with four years, a t of 2 has p = 0.14). “Some evidence” means p under 5%, “strong evidence” p under 1% over at least six years.

Companies traded

CompanyTitle on the latest filingPurchasesSalesFirst reportLatest report
Kingsway Corp KWY —163September 17, 2018December 17, 2025
Wheeler Real Estate Investment Trust, Inc. WHLR —10December 22, 2023December 22, 2023

Trades and what followed

Moves are against the S&P 500; green means the trade went the insider’s way.

ReportedTradedCompanyTradeValue3 months after report12 months after report12 months after trade
December 17, 2025December 15, 2025 KWY Sale $572,134 −15.3%not yetnot yet
August 20, 2025August 18, 2025 KWY Sale $1,003,035 −16.6%−45.8%−50.7%
December 22, 2023December 20, 2023 WHLR Purchase $145,387 not yetnot yetnot yet
March 15, 2023March 13, 2023 KWY Sale $1,448,250 −16.3%−37.7%−40.3%
June 2, 2022May 31, 2022 KWY Purchase $107,800 +29.6%+61.0%+56.1%
May 24, 2022May 20, 2022 KWY Purchase $51,047 +27.6%+43.3%+56.4%
March 28, 2022March 24, 2022 KWY Purchase $110,000 +19.6%+72.0%+66.9%
March 18, 2022March 16, 2022 KWY Purchase $110,000 +8.7%+73.4%+66.7%
March 14, 2022March 10, 2022 KWY Purchase $61,666 +8.2%+71.5%+68.7%
December 15, 2021December 13, 2021 KWY Purchase $109,500 +3.2%+48.0%+45.6%
December 10, 2021December 8, 2021 KWY Purchase $52,452 +8.7%+45.6%+50.6%
November 22, 2021November 18, 2021 KWY Purchase $110,000 +3.9%+43.3%+44.2%
April 1, 2021March 31, 2021 KWY Purchase $741,846 not yetnot yetnot yet
January 4, 2021December 30, 2020 KWY Purchase $118,050 not yetnot yetnot yet
December 15, 2020December 11, 2020 KWY Purchase $84,714 not yetnot yetnot yet
September 10, 2020September 8, 2020 KWY Purchase $147,000 not yetnot yetnot yet
August 28, 2020August 26, 2020 KWY Purchase $241,578 not yetnot yetnot yet
November 16, 2018November 14, 2018 KWY Purchase $54,400 not yetnot yetnot yet
September 27, 2018September 25, 2018 KWY Purchase $40,710 not yetnot yetnot yet
September 17, 2018September 13, 2018 KWY Purchase $213,750 not yetnot yetnot yet

Open-market purchases and sales of at least $10,000 in companies we cover, from SEC Form 4 filings; sales made under a pre-set Rule 10b5-1 plan are not shown. “Not yet” means the window has not finished or the share price was under $5 at entry. These are the shares’ moves after each trade: they say nothing about why Stilwell Associates, L.P. traded and do not suggest the use of non-public information. How every insider compares · the insider trading backtest.