James D. Small III serves as Executive at OVERSEAS SHIPHOLDING GROUP INC, where they oversee executive responsibilities. Since joining the company, James D. Small III has executed 114 insider transactions totaling $4.2M, demonstrating a bearish approach to their equity position. Their most recent transaction on Nov 14, 2025 involved selling 20,000 shares valued at $1.1M.
James D. Small III currently holds 49,292 shares of OVERSEAS SHIPHOLDING GROUP INC (OSG), valued at approximately $0. This represents their equity stake as Executive.
Based on SEC Form 4 filings, James D. Small III has been a net seller of OSG stock. They have purchased $0 and sold $4.2M worth of shares.
James D. Small III's most recent insider trade was on Nov 14, 2025, when they sold 20,000 shares at $53.60 per share.
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| $41.35 |
| Discretionary |
| Jun 14, 2024 | INSW | $414.0K | Sale | 7,500 | $55.20 | Discretionary |
| Apr 7, 2024 | INSW | $0 | Other | 15,298 | $N/A | Discretionary |
| Apr 7, 2024 | INSW | $0 | Payment | 8,337 | $N/A | Discretionary |
| Mar 15, 2024 | INSW | $0 | Other | 3,122 | $N/A | Discretionary |
| Mar 15, 2024 | INSW | $0 | Payment | 1,656 | $N/A | Discretionary |
| Mar 8, 2024 | INSW | $0 | Payment | 1,212 | $N/A | Discretionary |
| Mar 8, 2024 | INSW | $0 | Other | 2,300 | $N/A | Discretionary |
| Feb 29, 2024 | INSW | $0 | Payment | 6,084 | $N/A | Discretionary |
| Feb 29, 2024 | INSW | $0 | Other | 11,180 | $N/A | Discretionary |
| Jan 17, 2024 | INSW | $384.4K | Payment | 7,439 | $51.68 | Discretionary |
| Jan 17, 2024 | INSW | $219.8K | Option Exercise | 10,184 | $21.58 | Discretionary |
| Jan 17, 2024 | INSW | $403.7K | Payment | 7,812 | $51.68 | Discretionary |
| Jan 17, 2024 | INSW | $228.9K | Option Exercise | 10,438 | $21.93 | Discretionary |
| Jan 17, 2024 | INSW | $219.8K | Option Exercise | 10,184 | $21.58 | Discretionary |
| Jan 17, 2024 | INSW | $406.0K | Payment | 7,856 | $51.68 | Discretionary |
| Jan 17, 2024 | INSW | $228.9K | Option Exercise | 10,438 | $21.93 | Discretionary |
| Jan 17, 2024 | INSW | $385.3K | Payment | 7,456 | $51.68 | Discretionary |
| Dec 15, 2023 | INSW | $21.5K | Sale | 500 | $42.96 | Planned |
| Nov 15, 2023 | INSW | $479.5K | Sale | 10,000 | $47.95 | Discretionary |
| Nov 15, 2023 | INSW | $24.0K | Sale | 500 | $47.97 | Planned |
| Oct 16, 2023 | INSW | $23.1K | Sale | 500 | $46.30 | Planned |
| Sep 15, 2023 | INSW | $20.6K | Sale | 500 | $41.18 | Planned |
| Aug 15, 2023 | INSW | $22.4K | Sale | 500 | $44.79 | Planned |
| Aug 11, 2023 | INSW | $903.6K | Sale | 20,000 | $45.18 | Discretionary |
| Jul 27, 2023 | INSW | $40.0K | Sale | 1,000 | $40.00 | Planned |
| May 15, 2023 | INSW | $20.0K | Sale | 500 | $40.00 | Planned |
| Apr 17, 2023 | INSW | $20.3K | Sale | 500 | $40.50 | Planned |
| Apr 7, 2023 | INSW | $0 | Other | 15,298 | $N/A | Discretionary |