Casey Chafkin serves as Executive at Skillz Inc., where they oversee executive responsibilities. Since joining the company, Casey Chafkin has executed 23 insider transactions totaling $40.1M, demonstrating a bearish approach to their equity position. Their most recent transaction on Dec 22, 2025 involved exercising options for 917 shares valued at $0.
Casey Chafkin currently holds 770,525 shares of Skillz Inc. (SKLZ), valued at approximately $0. This represents their equity stake as Executive.
Based on SEC Form 4 filings, Casey Chafkin has been a net seller of SKLZ stock. They have purchased $1.0M and sold $39.1M worth of shares.
Casey Chafkin's most recent insider trade was on Dec 22, 2025, when they sold 917 shares at $0.00 per share.
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| $N/A |
| Discretionary |
| Sep 12, 2024 | SKLZ | $0 | Option Exercise | 916 | $N/A | Discretionary |
| Sep 4, 2024 | SKLZ | $0 | Option Exercise | 3,372 | $N/A | Discretionary |
| Sep 4, 2024 | SKLZ | $0 | Option Exercise | 916 | $N/A | Discretionary |
| Mar 14, 2024 | SKLZ | $0 | Option Exercise | 3,372 | $N/A | Discretionary |
| Mar 4, 2024 | SKLZ | $0 | Option Exercise | 916 | $N/A | Discretionary |
| Dec 14, 2023 | SKLZ | $0 | Option Exercise | 3,372 | $N/A | Discretionary |
| Dec 5, 2023 | SKLZ | $0 | Option Exercise | 916 | $N/A | Discretionary |
| Sep 18, 2023 | SKLZ | $0 | Option Exercise | 3,372 | $N/A | Discretionary |
| Sep 5, 2023 | SKLZ | $0 | Option Exercise | 916 | $N/A | Discretionary |
| Aug 8, 2023 | SKLZ | $87.8K | Option Exercise | 87,805 | $1.00 | Discretionary |
| Jun 14, 2023 | SKLZ | $0 | Option Exercise | 67,450 | $N/A | Discretionary |
| Jun 4, 2023 | SKLZ | $0 | Option Exercise | 18,323 | $N/A | Discretionary |
| Mar 14, 2023 | SKLZ | $0 | Option Exercise | 269,800 | $N/A | Discretionary |
| Mar 4, 2023 | SKLZ | $0 | Option Exercise | 18,323 | $N/A | Discretionary |
| Dec 4, 2022 | SKLZ | $0 | Option Exercise | 18,323 | $N/A | Discretionary |
| Sep 4, 2022 | SKLZ | $22.9K | Option Exercise | 18,323 | $1.25 | Discretionary |
| Jun 4, 2022 | SKLZ | $0 | Option Exercise | 18,323 | $N/A | Discretionary |
| Mar 4, 2022 | SKLZ | $0 | Option Exercise | 73,292 | $N/A | Discretionary |
| Nov 8, 2021 | SKLZ | $1.0M | Purchase | 86,500 | $11.63 | Discretionary |
| Mar 23, 2021 | SKLZ | $39.1M | Sale | 1,673,599 | $23.34 | Discretionary |
| Mar 5, 2021 | SKLZ | $0 | Conversion | 260,856 | $N/A | Discretionary |