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Joseph Stilwell Insider Profile

102 Followers
Joseph Stilwell, Director, Ten Percent Owner at Kingsway Financial Services, holds 1.53M shares in Kingsway Financial Services (Ticker: KFS), holds 537.62K shares in Wheeler Real Estate Investment (Ticker: WHLR), holds 679.20K shares in Peoples Financial (Ticker: PFBX). Most recently, Joseph Stilwell Sold ― shares of Kingsway Financial Services on Jul 01, 2025 for an estimated value of 2.26M.
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Joseph Stilwell

Joseph Stilwell
Kingsway Financial Services (KFS)
Director, Ten Percent Owner

Ranked #55 out of 102,674 Corporate Insiders

Profitable Transactions

77%
227 out of 296 Profitable Transactions

Average Return

+16.90%
Average return per transaction
Time Frame
1 Year
Compare to
No Benchmark

Insider Holdings

$76M
26.75%
24.60%
23.65%
17.82%
7.17% Others
A breakdown of Joseph Stilwell's holdings

Insider Roles

Kingsway Financial Services
(KFS)
Director, Ten Percent Owner
Sound Financial Bancorp
(SFBC)
Ten Percent Owner
Provident Bancorp
(PVBC)
Ten Percent Owner
Peoples Financial
(PFBX)
Ten Percent Owner
+2 other positions
Roles that Joseph Stilwell holds in companies

Most Profitable Insider Trade

Stock:
Wheeler Real Estate Investment
(WHLR)
Rating:Informative Buy
Date:Jun 23, 2020 - Jun 23, 2021
Return:+206.20%
The most profitable trade made by Joseph Stilwell

Joseph Stilwell's Trading History

Company Name
Last Transaction Date
Insider Position
Last Transaction
Last Transaction Amount
Holding Value
Kingsway Financial Services
Jul 01, 2025
Director, Ten Percent Owner
Informative Sell
2.26M
$20.40M
Wheeler Real Estate Investment
Jun 13, 2025
Director, Ten Percent Owner
Informative Buy
1.51M
$1.84M
Sound Financial Bancorp
Feb 02, 2024
Ten Percent Owner
Informative Buy
50.82K
$18.76M
Peoples Financial
May 29, 2025
Ten Percent Owner
Informative Buy
48.75K
$13.59M
Provident Bancorp
Jun 06, 2024
Ten Percent Owner
Informative Sell
721.50K
$18.03M
American Coastal Insurance
Oct 23, 2012
Ten Percent Owner
Informative Sell
11.75K
$3.62M
List of latest transactions for each holding click on a transaction to see Joseph Stilwell's performance on stock

Joseph Stilwell insider profile FAQ

What is the percentage of profitable transactions made by Joseph Stilwell?
The percentage of profitable transactions made by Joseph Stilwell is 77%.
    What is the average return per transaction made by Joseph Stilwell?
    The average return per transaction made by Joseph Stilwell is 16.90%.
      What stocks does Joseph Stilwell hold?
      Joseph Stilwell holds: KFS, WHLR, SFBC, PFBX, PVBC, ACIC stocks.
        What was Joseph Stilwell’s latest transaction?
        Joseph Stilwell latest transaction was an Informative Sell of $2.26M.
          What was Joseph Stilwell's most profitable transaction?
          Joseph Stilwell’s most profitable transaction was an Informative Buy of WHLR stock on June 23, 2020. The return on the trade was 206.20%.
            What is Joseph Stilwell's role in Kingsway Financial Services?
            Joseph Stilwell's role in Kingsway Financial Services is Director, Ten Percent Owner.
              How can I follow the stock ratings of top corporate insiders?
              Head over to our Expert Center to see a list of the Top 100 corporate insiders and follow the corporate insiders of your choice. Visit their profiles for more details about their stock transactions and see how they perform on a stock-by-stock basis.