The most recent Oscar Health (OSCR) insider transaction: William Gassen (Director) received 698 shares as a grant or award on Oct 8, 2026, reported on Form 4 on Oct 13, 2026. So far in the quarter ending Dec 31, 2026, insider holdings showed no net buying or selling.
Across the past 12 months, open-market trades by Oscar Health insiders totaled $11.92 million in purchases (1Mn shares) and $150.02 million in sales (5.6Mn shares).
| # | Insider | Position | Direct | Indirect | Total | Share of Insiders | Last Filed |
|---|---|---|---|---|---|---|---|
| 1 | Joshua Kushner | Co Founder And Vice Chairman | 0 | 35,595,243 | 35,595,243 | 42.1% | 18 Sep, 2026 |
| 2 | Partners Ii Gp, Llc Thrive | Director, TenPercentOwner | 0 | 29,251,626 | 29,251,626 | 34.6% | 18 Sep, 2026 |
| 3 | Mark T Bertolini | Chief Executive Officer | 7,751,570 | 0 | 7,751,570 | 9.2% | 01 Jul, 2026 |
| 4 | Partners Vii Growth Gp, Llc Thrive | Director, TenPercentOwner | 0 | 6,343,617 | 6,343,617 | 7.5% | 22 Nov, 2024 |
| 5 | Mario Schlosser | President Of Technology Cto | 1,661,737 | 0 | 1,661,737 | 2.0% | 08 Sep, 2026 |
| 6 | Richard Scott Blackley | Chief Financial Officer | 1,046,108 | 0 | 1,046,108 | 1.2% | 08 Sep, 2026 |
| 7 | Jeffery H Boyd | Director | 705,673 | 0 | 705,673 | 0.8% | 06 Jun, 2025 |
| 8 | Alessandrea C. Quane | Evp, Chief Insurance Officer | 430,216 | 0 | 430,216 | 0.5% | 09 Dec, 2024 |
| 9 | Janet Liang | President, Oscar Insurance | 248,697 | 0 | 248,697 | 0.3% | 08 Sep, 2026 |
| 10 | Ranmali Bopitiya | Evp Chief Legal Officer | 241,488 | 0 | 241,488 | 0.3% | 03 Dec, 2024 |
| 11 | Victoria Baltrus | Chief Accounting Officer | 213,631 | 0 | 213,631 | 0.3% | 08 Sep, 2026 |
| 12 | Adam Mcananey | Chief Legal Officer | 209,004 | 0 | 209,004 | 0.2% | 08 Sep, 2026 |
| 13 | David Plouffe | Director | 137,121 | 0 | 137,121 | 0.2% | 08 Jun, 2026 |
| 14 | Vanessa Ames Wittman | Director | 112,121 | 0 | 112,121 | 0.1% | 22 Sep, 2026 |
| 15 | Steven Wolin | Chief Operating Officer | 102,598 | 0 | 102,598 | 0.1% | 03 Dec, 2024 |
| 16 | Jr Charles E Phillips | Director | 85,787 | 0 | 85,787 | 0.1% | 13 Jun, 2022 |
| 17 | Laura W Lang | Director | 82,840 | 0 | 82,840 | 0.1% | 08 Jun, 2026 |
| 18 | William Gassen | Director | 82,840 | 0 | 82,840 | 0.1% | 08 Jun, 2026 |
| 19 | Elbert O. Jr. Robinson | Director | 64,512 | 0 | 64,512 | 0.1% | 14 May, 2025 |
| 20 | Meghan V. Joyce | Chief Operating Officer | 43,070 | 0 | 43,070 | 0.1% | 03 Mar, 2022 |
| 21 | Dennis Weaver | Chief Clinical Officer | 27,110 | 0 | 27,110 | 0.0% | 05 Dec, 2022 |
| 22 | Sid Sankaran | Interim Cfo | 22,609 | 0 | 22,609 | 0.0% | 08 Jun, 2026 |
Each row is that insider’s most recently reported position, from Form 4 filings over the last 60 months — which is why this total does not tie to the quarterly series above, where a quarter counts only the insiders who filed in it. Shares held through a fund or institutional portfolio are counted on the institutional ownership page instead.
| Date | Insider | Position | Transaction | Shares | Price | Value | Shares Held After | Ownership |
|---|---|---|---|---|---|---|---|---|
| 08 Oct, 2026 | William Gassen | Director | Acquired A | 698 | $33.10 | $23.10K | 7,769 | Direct |
| 08 Oct, 2026 | Sid Sankaran | Director | Acquired A | 1,472 | $33.10 | $48.72K | 3,533 | Direct |
| 08 Oct, 2026 | David Plouffe | Director | Acquired A | 641 | $33.10 | $21.22K | 8,176 | Direct |
| 18 Sep, 2026 | Vanessa Ames Wittman | Director | Disposed S | 25,000 | $32.24 | $806.00K | 112,121 | Direct |
| 18 Sep, 2026 | Partners Ii Gp, Llc Thrive | Director, TenPercentOwner | Disposed J | 6,268,097 | $0.00 | $0 | 0 | Indirect |
| 18 Sep, 2026 | Joshua Kushner | Co Founder And Vice Chairman | Disposed J | 6,268,097 | $0.00 | $0 | 0 | Indirect |
| 18 Sep, 2026 | Partners Ii Gp, Llc Thrive | Director, TenPercentOwner | Disposed J | 75,520 | $0.00 | $0 | 0 | Indirect |
| 18 Sep, 2026 | Joshua Kushner | Co Founder And Vice Chairman | Disposed J | 75,520 | $0.00 | $0 | 0 | Indirect |
| 18 Sep, 2026 | Partners Ii Gp, Llc Thrive | Director, TenPercentOwner | Acquired J | 1,323,589 | $0.00 | $0 | 1,323,589 | Indirect |
| 18 Sep, 2026 | Joshua Kushner | Co Founder And Vice Chairman | Acquired J | 1,323,589 | $0.00 | $0 | 1,323,589 | Indirect |
| 18 Sep, 2026 | Partners Ii Gp, Llc Thrive | Director, TenPercentOwner | Acquired J | 4,855,810 | $0.00 | $0 | 4,855,810 | Indirect |
| 18 Sep, 2026 | Joshua Kushner | Co Founder And Vice Chairman | Acquired J | 4,855,810 | $0.00 | $0 | 4,855,810 | Indirect |
| 18 Sep, 2026 | Partners Ii Gp, Llc Thrive | Director, TenPercentOwner | Acquired J | 164,218 | $0.00 | $0 | 164,218 | Indirect |
| 18 Sep, 2026 | Joshua Kushner | Co Founder And Vice Chairman | Acquired J | 164,218 | $0.00 | $0 | 164,218 | Indirect |
| 18 Sep, 2026 | Joshua Kushner | Co Founder And Vice Chairman | Disposed J | 1,323,589 | $0.00 | $0 | 0 | Indirect |
| 18 Sep, 2026 | Partners Ii Gp, Llc Thrive | Director, TenPercentOwner | Disposed J | 1,323,589 | $0.00 | $0 | 0 | Indirect |
| 18 Sep, 2026 | Joshua Kushner | Co Founder And Vice Chairman | Disposed J | 4,855,810 | $0.00 | $0 | 0 | Indirect |
| 18 Sep, 2026 | Partners Ii Gp, Llc Thrive | Director, TenPercentOwner | Disposed J | 4,855,810 | $0.00 | $0 | 0 | Indirect |
| 18 Sep, 2026 | Joshua Kushner | Co Founder And Vice Chairman | Disposed J | 164,218 | $0.00 | $0 | 0 | Indirect |
| 18 Sep, 2026 | Partners Ii Gp, Llc Thrive | Director, TenPercentOwner | Disposed J | 164,218 | $0.00 | $0 | 0 | Indirect |