Insider Transactions last 24 months for Kingsway Financial Services, Inc. - NYSE: KFS
Transactions
All
Buy
Sell
Option Exercise
Filer's Name
Relationship/ Title
Trans.
Date
Trans. Type
Ownership Type
Security Type
Shares
Price
Trans.
Value
Total Shares Owned
Fitzgerald John Taylor Maloney President and CEO 03/30/2026 AP Direct COM 244 $10.22 $2,493.68 1,460,971 Hansen Kent A CFO & EVP 03/30/2026 AP Direct COM 153 $10.22 $1,563.66 120,260 Hansen Kent A CFO & EVP 03/13/2026 AP Direct COM 146 $10.71 $1,563.66 120,107 Fitzgerald John Taylor Maloney President and CEO 03/13/2026 AP Direct COM 234 $10.71 $2,506.14 1,460,727 Fitzgerald John Taylor Maloney President and CEO 02/27/2026 AP Direct COM 202 $12.34 $2,492.68 1,460,493 Hansen Kent A CFO & EVP 02/27/2026 AP Direct COM 126 $12.34 $1,554.84 119,961 Fitzgerald John Taylor Maloney President and CEO 02/17/2026 AP Direct COM 205 $12.19 $2,498.95 1,460,291 Hansen Kent A CFO & EVP 02/17/2026 AP Direct COM 128 $12.19 $1,560.32 119,835 Hansen Kent A CFO & EVP 02/02/2026 AP Direct COM 114 $13.69 $1,560.66 119,707 Fitzgerald John Taylor Maloney President and CEO 02/02/2026 AP Direct COM 183 $13.69 $2,505.27 1,460,086 Hansen Kent A CFO & EVP 01/15/2026 AP Direct COM 116 $13.54 $1,570.64 119,593 Fitzgerald John Taylor Maloney President and CEO 01/15/2026 AP Direct COM 185 $13.54 $2,504.90 1,459,903 Fitzgerald John Taylor Maloney President and CEO 12/31/2025 AP Direct COM 184 $13.58 $2,498.72 1,459,718 Hansen Kent A CFO & EVP 12/31/2025 AP Direct COM 115 $13.58 $1,561.70 119,477 Hansen Kent A CFO & EVP 12/30/2025 DF Direct COM 2,919 $12.83 $37,450.77 119,362 Hansen Kent A CFO & EVP 12/30/2025 DF Direct COM 3,004 $12.83 $38,541.32 122,281 Hansen Kent A CFO & EVP 12/30/2025 DF Direct COM 3,565 $12.83 $45,738.95 125,285 Hansen Kent A CFO & EVP 12/29/2025 DS Direct COM 7,500 $13.67 $102,508.50 128,850 Fitzgerald John Taylor Maloney President and CEO 12/23/2025 DS Direct COM 30,000 $13.32 $399,714.00 1,459,534 Stilwell Joseph Director 12/22/2025 DS Indirect COM 19,229 $12.80 $246,131.20 300,000 Patinkin Adam Jonathan Director 12/17/2025 AX Indirect COM 500,000 $8.25 $4,125,000.00 1,524,000 Patinkin Adam Jonathan Director 12/17/2025 AX Indirect COM 540,000 $8.25 $4,455,000.00 1,024,000 Patinkin Adam Jonathan Director 12/17/2025 AX Indirect COM 275,000 $8.25 $2,268,750.00 1,023,000 Horowitz Joshua Director 12/17/2025 AX Indirect COM 252,500 $8.25 $2,083,125.00 367,500 Horowitz Joshua Director 12/17/2025 AX Direct COM 22,500 $8.25 $185,625.00 32,500
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Filer's Name
Relationship/ Title
Trans.
Date
Trans. Type
Ownership Type
Security Type
Shares
Price
Trans.
Value
Total Shares Owned
Fitzgerald John Taylor Maloney President and CEO 03/30/2026 AP Direct COM 244 $10.22 $2,493.68 1,460,971 Hansen Kent A CFO & EVP 03/30/2026 AP Direct COM 153 $10.22 $1,563.66 120,260 Hansen Kent A CFO & EVP 03/13/2026 AP Direct COM 146 $10.71 $1,563.66 120,107 Fitzgerald John Taylor Maloney President and CEO 03/13/2026 AP Direct COM 234 $10.71 $2,506.14 1,460,727 Fitzgerald John Taylor Maloney President and CEO 02/27/2026 AP Direct COM 202 $12.34 $2,492.68 1,460,493 Hansen Kent A CFO & EVP 02/27/2026 AP Direct COM 126 $12.34 $1,554.84 119,961 Fitzgerald John Taylor Maloney President and CEO 02/17/2026 AP Direct COM 205 $12.19 $2,498.95 1,460,291 Hansen Kent A CFO & EVP 02/17/2026 AP Direct COM 128 $12.19 $1,560.32 119,835 Hansen Kent A CFO & EVP 02/02/2026 AP Direct COM 114 $13.69 $1,560.66 119,707 Fitzgerald John Taylor Maloney President and CEO 02/02/2026 AP Direct COM 183 $13.69 $2,505.27 1,460,086 Hansen Kent A CFO & EVP 01/15/2026 AP Direct COM 116 $13.54 $1,570.64 119,593 Fitzgerald John Taylor Maloney President and CEO 01/15/2026 AP Direct COM 185 $13.54 $2,504.90 1,459,903 Fitzgerald John Taylor Maloney President and CEO 12/31/2025 AP Direct COM 184 $13.58 $2,498.72 1,459,718 Hansen Kent A CFO & EVP 12/31/2025 AP Direct COM 115 $13.58 $1,561.70 119,477 Fitzgerald John Taylor Maloney President and CEO 12/16/2025 AP Direct COM 195 $12.82 $2,499.90 1,489,534 Hansen Kent A CFO & EVP 12/16/2025 AP Direct COM 122 $12.82 $1,564.04 136,472 Hansen Kent A CFO & EVP 11/28/2025 AP Direct COM 120 $13.03 $1,563.60 136,350 Fitzgerald John Taylor Maloney President and CEO 11/28/2025 AP Direct COM 192 $13.03 $2,501.76 1,489,339 Fitzgerald John Taylor Maloney President and CEO 11/17/2025 AP Direct COM 197 $12.70 $2,501.90 1,489,147 Hansen Kent A CFO & EVP 11/17/2025 AP Direct COM 123 $12.70 $1,562.10 136,230 Fitzgerald John Taylor Maloney President and CEO 10/30/2025 AP Direct COM 177 $14.08 $2,492.16 1,488,950 Hansen Kent A CFO & EVP 10/30/2025 AP Direct COM 111 $14.08 $1,562.88 136,107 Fitzgerald John Taylor Maloney President and CEO 10/15/2025 AP Direct COM 157 $15.92 $2,499.44 1,488,773 Hansen Kent A CFO & EVP 10/15/2025 AP Direct COM 98 $15.92 $1,560.16 135,996 Hansen Kent A CFO & EVP 09/30/2025 AP Direct COM 107 $14.63 $1,565.41 135,898
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Filer's Name
Relationship/ Title
Trans.
Date
Trans. Type
Ownership Type
Security Type
Shares
Price
Trans.
Value
Total Shares Owned
Hansen Kent A CFO & EVP 12/30/2025 DF Direct COM 2,919 $12.83 $37,450.77 119,362 Hansen Kent A CFO & EVP 12/30/2025 DF Direct COM 3,004 $12.83 $38,541.32 122,281 Hansen Kent A CFO & EVP 12/30/2025 DF Direct COM 3,565 $12.83 $45,738.95 125,285 Hansen Kent A CFO & EVP 12/29/2025 DS Direct COM 7,500 $13.67 $102,508.50 128,850 Fitzgerald John Taylor Maloney President and CEO 12/23/2025 DS Direct COM 30,000 $13.32 $399,714.00 1,459,534 Stilwell Joseph Director 12/22/2025 DS Indirect COM 19,229 $12.80 $246,131.20 300,000 Stilwell Joseph Director 12/16/2025 DS Indirect COM 10,429 $12.80 $133,491.20 534,706 Stilwell Joseph Director 12/15/2025 DS Indirect COM 34,269 $12.80 $438,660.33 545,135 Stilwell Joseph Director 12/11/2025 DS Indirect COM 67,500 $12.80 $864,000.00 579,404 Stilwell Joseph Director 12/09/2025 DS Indirect COM 20,000 $12.80 $256,000.00 646,904 Stilwell Joseph Director 12/08/2025 DS Indirect COM 35,000 $12.82 $448,700.00 666,904 Fitzgerald John Taylor Maloney President and CEO 09/26/2025 DJ Direct COM 14,100 $14.57 $205,437.00 1,488,445 Fitzgerald John Taylor Maloney President and CEO 09/26/2025 DJ Direct COM 14,100 $14.57 $205,437.00 1,502,545 Fitzgerald John Taylor Maloney President and CEO 09/26/2025 DJ Direct COM 14,100 $14.57 $205,437.00 1,516,645 Stilwell Joseph Director 09/17/2025 DS Indirect COM 14,288 $14.47 $206,747.36 590,410 Stilwell Joseph Director 09/17/2025 DS Indirect COM 5,055 $14.47 $73,145.85 457,181 Stilwell Joseph Director 09/17/2025 DS Indirect COM 28,657 $14.47 $414,666.79 3,550,382 Stilwell Joseph Director 09/16/2025 DS Indirect COM 5,953 $14.40 $85,723.20 604,698 Stilwell Joseph Director 09/16/2025 DS Indirect COM 2,106 $14.40 $30,326.40 462,236 Stilwell Joseph Director 09/16/2025 DS Indirect COM 11,941 $14.40 $171,950.40 3,579,039 Stilwell Joseph Director 09/08/2025 DS Indirect COM 7,505 $14.41 $108,147.05 610,651 Stilwell Joseph Director 09/08/2025 DS Indirect COM 2,551 $14.41 $36,759.91 464,342 Stilwell Joseph Director 09/08/2025 DS Indirect COM 14,944 $14.41 $215,343.04 3,590,980 Stilwell Joseph Director 08/22/2025 DS Indirect COM 22,586 $14.18 $320,233.34 618,156 Stilwell Joseph Director 08/22/2025 DS Indirect COM 7,642 $14.18 $108,351.33 466,893
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Filer's Name
Relationship/ Title
Trans.
Date
Trans. Type
Ownership Type
Security Type
Shares
Price
Trans.
Value
Total Shares Owned
Patinkin Adam Jonathan Director 12/17/2025 AX Indirect COM 500,000 $8.25 $4,125,000.00 1,524,000 Patinkin Adam Jonathan Director 12/17/2025 AX Indirect COM 540,000 $8.25 $4,455,000.00 1,024,000 Patinkin Adam Jonathan Director 12/17/2025 AX Indirect COM 275,000 $8.25 $2,268,750.00 1,023,000 Horowitz Joshua Director 12/17/2025 AX Indirect COM 252,500 $8.25 $2,083,125.00 367,500 Horowitz Joshua Director 12/17/2025 AX Direct COM 22,500 $8.25 $185,625.00 32,500 Hannon Gregory Paul Director 12/17/2025 DX Indirect COM 500,000 $8.25 $4,125,000.00 1,987,830 Kavanagh Terence Michael Director 12/17/2025 DX Indirect COM 500,000 $8.25 $4,125,000.00 1,987,830 Oakmont Capital Inc Other 12/17/2025 DX Direct COM 500,000 $8.25 $4,125,000.00 1,987,830 Stilwell Joseph Director 12/17/2025 DX Indirect COM 218,842 $8.25 $1,805,446.50 371,568 Stilwell Joseph Director 12/17/2025 DX Indirect COM 20,270 $8.25 $167,227.50 436,911 Stilwell Joseph Director 12/17/2025 DX Indirect COM 1,295,411 $8.25 $10,687,140.75 2,254,971 Stilwell Joseph Director 12/17/2025 DX Indirect COM 215,477 $8.25 $1,777,685.25 319,229
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Transaction Type Key
First letter: A = Acquired, D = Disposed
Second letter:
A = Grant, award or other acquisition pursuant to Rule 16b-3(d)
C = Conversion of derivative security |
D = Disposition to the issuer of issuer equity securities pursuant to Rule 16b-3(e) |
E = Expiration of short derivative position |
F = Payment of exercise price or tax liability by delivering or withholding securities incident to the receipt, exercise or vesting of a security issued in accordance with Rule 16b-3. |
G = Gift |
H = Expiration (or cancellation) of long derivative position with value received |
I = Discretionary transaction in accordance with Rule 16b-3(f) |
J = Other |
L = Small acquisition under Rule 16a-6 |
M = Exercise or conversion of derivative security exempted pursuant to Rule 16b-3 |
O = Exercise of out-of-the-money derivative security |
P = Open market or private purchase |
S = Open market or private sale |
U = Disposition pursuant to a tender of shares in a change of control transaction |
W = Acquisition or disposition by will or the laws of descent and distribution |
X = Exercise of in-the-money or at-the-money derivative security |
Z = Deposit into or withdrawal from voting trust
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