Patrick K. Callahan serves as Executive at PROGRESSIVE CORP/OH/, where they oversee executive responsibilities. Since joining the company, Patrick K. Callahan has executed 65 insider transactions totaling $23.9M, demonstrating a bearish approach to their equity position. Their most recent transaction on Jan 20, 2026 involved exercising options for 6,270.07 shares valued at $0.
Patrick K. Callahan currently holds 11,818.93 shares of PROGRESSIVE CORP/OH/ (PGR), valued at approximately $0. This represents their equity stake as Executive.
Based on SEC Form 4 filings, Patrick K. Callahan has been a net seller of PGR stock. They have purchased $0 and sold $23.9M worth of shares.
Patrick K. Callahan's most recent insider trade was on Jan 20, 2026, when they sold 6,270.07 shares at $0.00 per share.
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| $201.32 |
| Discretionary |
| Jan 20, 2026 | PGR | $0 | Option Exercise | 6,270.07 | $N/A | Discretionary |
| Sep 19, 2025 | PGR | $1.6M | Sale | 6,420 | $242.22 | Discretionary |
| Aug 22, 2025 | PGR | $1.6M | Sale | 6,232 | $249.96 | Discretionary |
| Jul 28, 2025 | PGR | $1.5M | Sale | 6,232 | $242.16 | Discretionary |
| Jul 25, 2025 | PGR | $3.6M | Payment | 14,629 | $249.44 | Discretionary |
| Jul 25, 2025 | PGR | $0 | Award | 33,514 | $N/A | Discretionary |
| Sep 20, 2024 | PGR | $2.0M | Sale | 7,696 | $255.21 | Planned |
| Aug 16, 2024 | PGR | $1.8M | Sale | 7,697 | $237.20 | Planned |
| Jul 22, 2024 | PGR | $1.7M | Sale | 7,930 | $214.01 | Planned |
| Jul 19, 2024 | PGR | $4.0M | Payment | 18,068 | $221.75 | Discretionary |
| Jul 19, 2024 | PGR | $0 | Award | 41,391.36 | $N/A | Discretionary |
| Feb 21, 2024 | PGR | $5.6M | Sale | 29,675 | $190.26 | Planned |
| Jan 16, 2024 | PGR | $149.7K | Payment | 886 | $168.93 | Discretionary |
| Jan 16, 2024 | PGR | $0 | Option Exercise | 2,266.8 | $N/A | Discretionary |
| Jan 1, 2024 | PGR | $0 | Option Exercise | 5,503.2 | $N/A | Discretionary |
| Jan 1, 2024 | PGR | $262.0K | Payment | 1,632 | $160.52 | Discretionary |
| Nov 27, 2023 | PGR | $3.1M | Payment | 18,922 | $163.74 | Discretionary |
| Nov 27, 2023 | PGR | $0 | Award | 43,347.41 | $N/A | Discretionary |
| Jan 4, 2023 | PGR | $475.0K | Sale | 3,644 | $130.36 | Discretionary |
| Jan 1, 2023 | PGR | $318.9K | Payment | 2,462 | $129.53 | Discretionary |
| Jan 1, 2023 | PGR | $0 | Option Exercise | 8,141.5 | $N/A | Discretionary |
| Sep 16, 2022 | PGR | $2.4M | Sale | 19,068 | $125.77 | Discretionary |
| Aug 25, 2022 | PGR | $1.8M | Payment | 14,321 | $125.95 | Discretionary |
| Aug 25, 2022 | PGR | $0 | Award | 33,389.91 | $N/A | Discretionary |
| Mar 22, 2022 | PGR | $364.7K | Sale | 3,231 | $112.87 | Discretionary |
| Feb 22, 2022 | PGR | $345.0K | Sale | 3,230 | $106.82 | Discretionary |
| Feb 1, 2022 | PGR | $349.6K | Sale | 3,230 | $108.25 | Discretionary |
| Jan 4, 2022 | PGR | $640.1K | Sale | 6,261 | $102.24 | Discretionary |