Kingsway Financial Services Inc (KFS)

Kingsway Financial Services witnessed eighteen insider trading transactions over the past ninety days, resulting in a net negative value of approximately $93,436. While executives consistently purchased shares, total selling activity outweighed these acquisitions. This period follows a 10.1% stock price decline, occurring ahead of the most recent August 2026 earnings report.
Ticker: KFS Exchange: NYS


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Insider trades have triggered activity signals for Kingsway Financial Services Inc. Upgrade to see score, net flow, insiders and the full signal context.

Top insiders
Trades
Abbreviations B: Buy, S: Sell, PP: Planned purchase, PlS: Planned sale, PrS: Proposed sale, O: Option / Other
3.9
Fitzgerald John Taylor Maloney President and CEO Executive Director
Transaction date
Purchase
Price
342.96
Quantity 72,274 -34.4%
Value US$4,092,344
3.4
Hansen Kent A CFO & EVP Officer
Transaction date
Purchase
Price
306.59
Quantity 40,730 +10.3%
Value US$641,823
3.4
Stilwell Joseph Non-Executive Director Large shareholder
Transaction date
Sale
Price
215.75
Quantity 68,612 +19.7%
Value US$633,396
3.4
Stilwell Joseph Non-Executive Director Large shareholder
Transaction date
Sale
Price
10.00
Quantity 1,000 -1.2%
Value US$100,000
3.4
Stilwell Joseph Non-Executive Director Large shareholder
Transaction date
Sale
Price
10.00
Quantity 1,000 -11.0%
Value US$100,000
3.4
Hansen Kent A CFO & EVP Officer
Transaction date
Purchase
Price
8.98
Quantity 1,000 +0.1%
Value US$100,000
3.4
Hansen Kent A CFO & EVP Officer
Transaction date
Purchase
Price
9.76
Quantity 161 +0.1%
Value US$1,571
3.4
Hansen Kent A CFO & EVP Officer
Transaction date
Purchase
Price
10.45
Quantity 149 +0.1%
Value US$1,557
3.4
Hansen Kent A CFO & EVP Officer
Transaction date
Purchase
Price
10.43
Quantity 150 +0.1%
Value US$1,564
3.4
Hansen Kent A CFO & EVP Officer
Transaction date
Purchase
Price
10.03
Quantity 156 +0.1%
Value US$1,565
3.3
Horowitz Joshua Non-Executive Director
Transaction date
Purchase
Price
9.91
Quantity 3,800 +1.0%
Value US$37,660
3.3
Horowitz Joshua Non-Executive Director
Transaction date
Purchase
Price
9.95
Quantity 700 +0.2%
Value US$6,965
3.9
Fitzgerald John Taylor Maloney President and CEO Executive Director
Transaction date
Sale
Price
10.14
Quantity 5,000 -14.7%
Value US$50,675
3.9
John T. Fitzgerald Officer Officer
Transaction date
Proposed sale
Price
10.23
Quantity 5,000
Value US$51,150
3.9
Fitzgerald John Taylor Maloney President and CEO Executive Director
Transaction date
Sale
Price
10.43
Quantity 5,000 -14.7%
Value US$52,144
3.9
John T. Fitzgerald Officer Officer
Transaction date
Proposed sale
Price
10.24
Quantity 5,000
Value US$51,200
3.9
Fitzgerald John Taylor Maloney President and CEO Executive Director
Transaction date
Sale
Price
10.30
Quantity 5,000 -14.7%
Value US$51,506
3.9
John T. Fitzgerald Officer Officer
Transaction date
Proposed sale
Price
10.44
Quantity 5,000
Value US$52,200
3.4
Hansen Kent A CFO & EVP Officer
Transaction date
Purchase
Price
10.85
Quantity 144 +0.1%
Value US$1,562
3.4
Hansen Kent A CFO & EVP Officer
Transaction date
Purchase
Price
10.93
Quantity 143 +0.1%
Value US$1,563
3.4
Hansen Kent A CFO & EVP Officer
Transaction date
Purchase
Price
10.22
Quantity 153 +0.1%
Value US$1,564
3.4
Hansen Kent A CFO & EVP Officer
Transaction date
Purchase
Price
10.71
Quantity 146 +0.1%
Value US$1,564
3.4
Hansen Kent A CFO & EVP Officer
Transaction date
Purchase
Price
12.34
Quantity 126 +0.1%
Value US$1,555
3.4
Hansen Kent A CFO & EVP Officer
Transaction date
Purchase
Price
12.19
Quantity 128 +0.1%
Value US$1,560
3.4
Hansen Kent A CFO & EVP Officer
Transaction date
Purchase
Price
13.69
Quantity 114 +0.1%
Value US$1,561
3.4
Hansen Kent A CFO & EVP Officer
Transaction date
Purchase
Price
13.54
Quantity 116 +0.1%
Value US$1,571
3.4
Hansen Kent A CFO & EVP Officer
Transaction date
Purchase
Price
13.58
Quantity 115 +0.1%
Value US$1,562
3.4
Hansen Kent A CFO & EVP Officer
Transaction date
Sale
Price
13.67
Quantity 7,500 -5.5%
Value US$102,508
3.4
Hansen Kent A Officer Officer
Transaction date
Proposed sale
Price
14.00
Quantity 7,500
Value US$105,000
3.9
John T. Fitzgerald Officer Officer
Transaction date
Proposed sale
Price
13.28
Quantity 30,000
Value US$398,400
3.4
Stilwell Joseph Non-Executive Director Large shareholder
Transaction date
Sale
Price
12.80
Quantity 19,229 -6.0%
Value US$246,131
3.4
Hansen Kent A CFO & EVP Officer
Transaction date
Purchase
Price
12.82
Quantity 122 +0.1%
Value US$1,564
3.4
Stilwell Joseph Non-Executive Director Large shareholder
Transaction date
Sale
Price
12.80
Quantity 10,429 -1.9%
Value US$133,491
3.4
Stilwell Joseph Non-Executive Director Large shareholder
Transaction date
Sale
Price
12.80
Quantity 34,269 -5.9%
Value US$438,660
3.4
Stilwell Joseph Non-Executive Director Large shareholder
Transaction date
Sale
Price
12.80
Quantity 67,500 -10.4%
Value US$864,000
3.4
Stilwell Joseph Non-Executive Director Large shareholder
Transaction date
Sale
Price
12.80
Quantity 20,000 -3.0%
Value US$256,000
3.4
Stilwell Joseph Non-Executive Director Large shareholder
Transaction date
Sale
Price
12.82
Quantity 35,000 -5.0%
Value US$448,700
3.4
Hansen Kent A CFO & EVP Officer
Transaction date
Purchase
Price
13.03
Quantity 120 +0.1%
Value US$1,564
3.4
Hansen Kent A CFO & EVP Officer
Transaction date
Purchase
Price
12.70
Quantity 123 +0.1%
Value US$1,562
3.4
Hansen Kent A CFO & EVP Officer
Transaction date
Purchase
Price
14.08
Quantity 111 +0.1%
Value US$1,563
3.4
Hansen Kent A CFO & EVP Officer
Transaction date
Purchase
Price
15.92
Quantity 98 +0.1%
Value US$1,560
3.4
Hansen Kent A CFO & EVP Officer
Transaction date
Purchase
Price
14.63
Quantity 107 +0.1%
Value US$1,565
3.4
Stilwell Joseph Non-Executive Director Large shareholder
Transaction date
Sale
Price
14.47
Quantity 14,288 -2.4%
Value US$206,747
3.4
Stilwell Joseph Non-Executive Director Large shareholder
Transaction date
Sale
Price
14.47
Quantity 5,055 -1.1%
Value US$73,146
3.4
Stilwell Joseph Non-Executive Director Large shareholder
Transaction date
Sale
Price
14.47
Quantity 28,657 -0.8%
Value US$414,667
3.4
Stilwell Joseph Non-Executive Director Large shareholder
Transaction date
Sale
Price
14.40
Quantity 5,953 -1.0%
Value US$85,723
3.4
Stilwell Joseph Non-Executive Director Large shareholder
Transaction date
Sale
Price
14.40
Quantity 2,106 -0.5%
Value US$30,326
3.4
Stilwell Joseph Non-Executive Director Large shareholder
Transaction date
Sale
Price
14.40
Quantity 11,941 -0.3%
Value US$171,950
3.4
Hansen Kent A CFO & EVP Officer
Transaction date
Purchase
Price
14.36
Quantity 109 +0.1%
Value US$1,565
3.4
Stilwell Joseph Non-Executive Director Large shareholder
Transaction date
Sale
Price
14.41
Quantity 7,505 -1.2%
Value US$108,147
3.4
Stilwell Joseph Non-Executive Director Large shareholder
Transaction date
Sale
Price
14.41
Quantity 2,551 -0.5%
Value US$36,760
3.4
Stilwell Joseph Non-Executive Director Large shareholder
Transaction date
Sale
Price
14.41
Quantity 14,944 -0.4%
Value US$215,343
Notification date Transaction date B/S Transaction type Insider and/or position Nb. shares
Price
Value
Number of shares Price Value Details
2026-08-18 2026-08-17 B Purchase

President and CEO

Executive Director
72,274 -34.4%
342.96
US$4,092,344
72,274 -34.4% 342.96 US$4,092,344
2026-08-18 2026-08-17 B Purchase

CFO & EVP

Officer
40,730 +10.3%
306.59
US$641,823
40,730 +10.3% 306.59 US$641,823
2026-08-17 2026-08-13 S Sale Non-Executive Director Large shareholder
68,612 +19.7%
215.75
US$633,396
68,612 +19.7% 215.75 US$633,396
2026-08-17 2026-08-13 S Sale Non-Executive Director Large shareholder
1,000 -1.2%
10.00
US$100,000
1,000 -1.2% 10.00 US$100,000
2026-08-17 2026-08-13 S Sale Non-Executive Director Large shareholder
1,000 -11.0%
10.00
US$100,000
1,000 -11.0% 10.00 US$100,000
2026-07-31 2026-07-30 B Purchase

CFO & EVP

Officer
1,000 +0.1%
8.98
US$100,000
1,000 +0.1% 8.98 US$100,000
2026-07-31 2026-07-30 B Purchase

President and CEO

Executive Director
1,000 +0.0%
8.98
US$100,000
1,000 +0.0% 8.98 US$100,000
2026-07-16 2026-07-15 B Purchase

President and CEO

Executive Director
256 +0.0%
9.76
US$2,499
256 +0.0% 9.76 US$2,499
2026-07-16 2026-07-15 B Purchase

CFO & EVP

Officer
161 +0.1%
9.76
US$1,571
161 +0.1% 9.76 US$1,571
2026-07-01 2026-06-30 B Purchase

CFO & EVP

Officer
149 +0.1%
10.45
US$1,557
149 +0.1% 10.45 US$1,557
2026-07-01 2026-06-30 B Purchase

President and CEO

Executive Director
239 +0.0%
10.45
US$2,498
239 +0.0% 10.45 US$2,498
2026-06-15 2026-06-15 B Purchase

CFO & EVP

Officer
150 +0.1%
10.43
US$1,564
150 +0.1% 10.43 US$1,564
2026-06-15 2026-06-15 B Purchase

President and CEO

Executive Director
240 +0.0%
10.43
US$2,503
240 +0.0% 10.43 US$2,503
2026-06-01 2026-05-29 B Purchase

CFO & EVP

Officer
156 +0.1%
10.03
US$1,565
156 +0.1% 10.03 US$1,565
2026-06-01 2026-05-29 B Purchase

President and CEO

Executive Director
250 +0.0%
10.03
US$2,508
250 +0.0% 10.03 US$2,508
2026-06-01 2026-05-29 B Purchase Non-Executive Director
3,800 +1.0%
9.91
US$37,660
3,800 +1.0% 9.91 US$37,660
2026-06-01 2026-05-28 B Purchase Non-Executive Director
700 +0.2%
9.95
US$6,965
700 +0.2% 9.95 US$6,965
2026-05-22 2026-05-21 S Sale

President and CEO

Executive Director
5,000 -14.7%
10.14
US$50,675
5,000 -14.7% 10.14 US$50,675
2026-05-21 2026-05-21 PrS Proposed sale

Officer

Officer
5,000
10.23
US$51,150
5,000 10.23 US$51,150
2026-05-21 2026-05-20 S Sale

President and CEO

Executive Director
5,000 -14.7%
10.43
US$52,144
5,000 -14.7% 10.43 US$52,144
2026-05-20 2026-05-20 PrS Proposed sale

Officer

Officer
5,000
10.24
US$51,200
5,000 10.24 US$51,200
2026-05-21 2026-05-19 S Sale

President and CEO

Executive Director
5,000 -14.7%
10.30
US$51,506
5,000 -14.7% 10.30 US$51,506
2026-05-19 2026-05-19 PrS Proposed sale

Officer

Officer
5,000
10.44
US$52,200
5,000 10.44 US$52,200
2026-05-19 2026-05-15 B Purchase

President and CEO

Executive Director
230 +0.0%
10.85
US$2,496
230 +0.0% 10.85 US$2,496
2026-05-19 2026-05-15 B Purchase

CFO & EVP

Officer
144 +0.1%
10.85
US$1,562
144 +0.1% 10.85 US$1,562
2026-05-04 2026-04-30 B Purchase

CFO & EVP

Officer
143 +0.1%
10.93
US$1,563
143 +0.1% 10.93 US$1,563
2026-05-04 2026-04-30 B Purchase

President and CEO

Executive Director
229 +0.0%
10.93
US$2,503
229 +0.0% 10.93 US$2,503
2026-04-15 2026-04-15 B Purchase

President and CEO

Executive Director
211 +0.0%
11.85
US$2,500
211 +0.0% 11.85 US$2,500
2026-03-31 2026-03-30 B Purchase

President and CEO

Executive Director
244 +0.0%
10.22
US$2,494
244 +0.0% 10.22 US$2,494
2026-03-31 2026-03-30 B Purchase

CFO & EVP

Officer
153 +0.1%
10.22
US$1,564
153 +0.1% 10.22 US$1,564
2026-03-16 2026-03-13 B Purchase

President and CEO

Executive Director
234 +0.0%
10.71
US$2,506
234 +0.0% 10.71 US$2,506
2026-03-16 2026-03-13 B Purchase

CFO & EVP

Officer
146 +0.1%
10.71
US$1,564
146 +0.1% 10.71 US$1,564
2026-03-02 2026-02-27 B Purchase

CFO & EVP

Officer
126 +0.1%
12.34
US$1,555
126 +0.1% 12.34 US$1,555
2026-03-02 2026-02-27 B Purchase

President and CEO

Executive Director
202 +0.0%
12.34
US$2,493
202 +0.0% 12.34 US$2,493
2026-02-18 2026-02-17 B Purchase

CFO & EVP

Officer
128 +0.1%
12.19
US$1,560
128 +0.1% 12.19 US$1,560
2026-02-18 2026-02-17 B Purchase

President and CEO

Executive Director
205 +0.0%
12.19
US$2,499
205 +0.0% 12.19 US$2,499
2026-02-02 2026-02-02 B Purchase

President and CEO

Executive Director
183 +0.0%
13.69
US$2,505
183 +0.0% 13.69 US$2,505
2026-02-02 2026-02-02 B Purchase

CFO & EVP

Officer
114 +0.1%
13.69
US$1,561
114 +0.1% 13.69 US$1,561
2026-01-29 2026-01-15 B Purchase

President and CEO

Executive Director
185 +0.0%
13.54
US$2,505
185 +0.0% 13.54 US$2,505
2026-01-29 2026-01-15 B Purchase

CFO & EVP

Officer
116 +0.1%
13.54
US$1,571
116 +0.1% 13.54 US$1,571
2026-01-05 2025-12-31 B Purchase

President and CEO

Executive Director
184 +0.0%
13.58
US$2,499
184 +0.0% 13.58 US$2,499
2026-01-05 2025-12-31 B Purchase

CFO & EVP

Officer
115 +0.1%
13.58
US$1,562
115 +0.1% 13.58 US$1,562
2025-12-31 2025-12-29 S Sale

CFO & EVP

Officer
7,500 -5.5%
13.67
US$102,508
7,500 -5.5% 13.67 US$102,508
2025-12-29 2025-12-29 PrS Proposed sale

Officer

Officer
7,500
14.00
US$105,000
7,500 14.00 US$105,000
2025-12-29 2025-12-23 S Sale

President and CEO

Executive Director
30,000 -2.0%
13.32
US$399,714
30,000 -2.0% 13.32 US$399,714
2025-12-23 2025-12-23 PrS Proposed sale

Officer

Officer
30,000
13.28
US$398,400
30,000 13.28 US$398,400
2025-12-29 2025-12-22 S Sale Non-Executive Director Large shareholder
19,229 -6.0%
12.80
US$246,131
19,229 -6.0% 12.80 US$246,131
2025-12-18 2025-12-16 B Purchase

CFO & EVP

Officer
122 +0.1%
12.82
US$1,564
122 +0.1% 12.82 US$1,564
2025-12-18 2025-12-16 B Purchase

President and CEO

Executive Director
195 +0.0%
12.82
US$2,500
195 +0.0% 12.82 US$2,500
2025-12-17 2025-12-16 S Sale Non-Executive Director Large shareholder
10,429 -1.9%
12.80
US$133,491
10,429 -1.9% 12.80 US$133,491
2025-12-17 2025-12-15 S Sale Non-Executive Director Large shareholder
34,269 -5.9%
12.80
US$438,660
34,269 -5.9% 12.80 US$438,660
2025-12-15 2025-12-11 S Sale Non-Executive Director Large shareholder
67,500 -10.4%
12.80
US$864,000
67,500 -10.4% 12.80 US$864,000
2025-12-10 2025-12-09 S Sale Non-Executive Director Large shareholder
20,000 -3.0%
12.80
US$256,000
20,000 -3.0% 12.80 US$256,000
2025-12-10 2025-12-08 S Sale Non-Executive Director Large shareholder
35,000 -5.0%
12.82
US$448,700
35,000 -5.0% 12.82 US$448,700
2025-12-02 2025-11-28 B Purchase

President and CEO

Executive Director
192 +0.0%
13.03
US$2,502
192 +0.0% 13.03 US$2,502
2025-12-02 2025-11-28 B Purchase

CFO & EVP

Officer
120 +0.1%
13.03
US$1,564
120 +0.1% 13.03 US$1,564
2025-11-19 2025-11-17 B Purchase

President and CEO

Executive Director
197 +0.0%
12.70
US$2,502
197 +0.0% 12.70 US$2,502
2025-11-19 2025-11-17 B Purchase

CFO & EVP

Officer
123 +0.1%
12.70
US$1,562
123 +0.1% 12.70 US$1,562
2025-11-03 2025-10-30 B Purchase

CFO & EVP

Officer
111 +0.1%
14.08
US$1,563
111 +0.1% 14.08 US$1,563
2025-11-03 2025-10-30 B Purchase

President and CEO

Executive Director
177 +0.0%
14.08
US$2,492
177 +0.0% 14.08 US$2,492
2025-10-17 2025-10-15 B Purchase

CFO & EVP

Officer
98 +0.1%
15.92
US$1,560
98 +0.1% 15.92 US$1,560
2025-10-17 2025-10-15 B Purchase

President and CEO

Executive Director
157 +0.0%
15.92
US$2,499
157 +0.0% 15.92 US$2,499
2025-10-02 2025-09-30 B Purchase

President and CEO

Executive Director
171 +0.0%
14.63
US$2,502
171 +0.0% 14.63 US$2,502
2025-10-02 2025-09-30 B Purchase

CFO & EVP

Officer
107 +0.1%
14.63
US$1,565
107 +0.1% 14.63 US$1,565
2025-09-18 2025-09-17 S Sale Non-Executive Director Large shareholder
14,288 -2.4%
14.47
US$206,747
14,288 -2.4% 14.47 US$206,747
2025-09-18 2025-09-17 S Sale Non-Executive Director Large shareholder
5,055 -1.1%
14.47
US$73,146
5,055 -1.1% 14.47 US$73,146
2025-09-18 2025-09-17 S Sale Non-Executive Director Large shareholder
28,657 -0.8%
14.47
US$414,667
28,657 -0.8% 14.47 US$414,667
2025-09-18 2025-09-16 S Sale Non-Executive Director Large shareholder
5,953 -1.0%
14.40
US$85,723
5,953 -1.0% 14.40 US$85,723
2025-09-18 2025-09-16 S Sale Non-Executive Director Large shareholder
2,106 -0.5%
14.40
US$30,326
2,106 -0.5% 14.40 US$30,326
2025-09-18 2025-09-16 S Sale Non-Executive Director Large shareholder
11,941 -0.3%
14.40
US$171,950
11,941 -0.3% 14.40 US$171,950
2025-09-16 2025-09-15 B Purchase

CFO & EVP

Officer
109 +0.1%
14.36
US$1,565
109 +0.1% 14.36 US$1,565
2025-09-16 2025-09-15 B Purchase

President and CEO

Executive Director
174 +0.0%
14.36
US$2,499
174 +0.0% 14.36 US$2,499
2025-09-10 2025-09-08 S Sale Non-Executive Director Large shareholder
7,505 -1.2%
14.41
US$108,147
7,505 -1.2% 14.41 US$108,147
2025-09-10 2025-09-08 S Sale Non-Executive Director Large shareholder
2,551 -0.5%
14.41
US$36,760
2,551 -0.5% 14.41 US$36,760
2025-09-10 2025-09-08 S Sale Non-Executive Director Large shareholder
14,944 -0.4%
14.41
US$215,343
14,944 -0.4% 14.41 US$215,343