| Date | Insider | Title | Code | Shares | Price | Value |
|---|---|---|---|---|---|---|
| Jul 1, 2026 | Schlosser Mario | Director | C | 47,500 | $0.0000 | $0.00 |
| Jul 1, 2026 | Schlosser Mario | Director | S | 30,228 | $31.6500 | $956.72K |
| Jul 1, 2026 | Schlosser Mario | Director | S | 13,672 | $30.8000 | $421.10K |
| Jul 1, 2026 | Schlosser Mario | Director | S | 3,600 | $29.5000 | $106.20K |
| Jul 1, 2026 | Schlosser Mario | Director | C | 47,500 | – | – |
| Jun 30, 2026 | Bertolini Mark T | Chief Executive Officer | S | 135,590 | $28.9700 | $3.93M |
| Jun 30, 2026 | Bertolini Mark T | Chief Executive Officer | S | 488,654 | $28.3500 | $13.85M |
| Jun 29, 2026 | Bertolini Mark T | Chief Executive Officer | S | 58,926 | $30.0800 | $1.77M |
| Jun 29, 2026 | Bertolini Mark T | Chief Executive Officer | S | 555,826 | $29.1700 | $16.21M |
| Jun 26, 2026 | Bertolini Mark T | Chief Executive Officer | S | 149,795 | $29.7900 | $4.46M |
| Jun 26, 2026 | Bertolini Mark T | Chief Executive Officer | S | 441,373 | $29.1100 | $12.85M |
| Jun 25, 2026 | Bertolini Mark T | Chief Executive Officer | S | 17,200 | $29.0800 | $500.18K |
| Jun 25, 2026 | Bertolini Mark T | Chief Executive Officer | S | 597,942 | $28.6000 | $17.10M |
| Jun 23, 2026 | Schlosser Mario | Director | C | 47,500 | $0.0000 | $0.00 |
| Jun 23, 2026 | Schlosser Mario | Director | C | 50,000 | $0.0000 | $0.00 |
| Jun 23, 2026 | Schlosser Mario | Director | C | 50,000 | $0.0000 | $0.00 |
| Jun 23, 2026 | Schlosser Mario | Director | C | 880,000 | $0.0000 | $0.00 |
| Jun 23, 2026 | Schlosser Mario | Director | M | 660,000 | $9.7500 | $6.43M |
| Jun 23, 2026 | Schlosser Mario | Director | M | 660,000 | $0.0000 | $0.00 |
| Jun 23, 2026 | Schlosser Mario | Director | S | 97 | $30.0900 | $2.92K |
| Jun 23, 2026 | Schlosser Mario | Director | S | 31,912 | $29.5800 | $943.96K |
| Jun 23, 2026 | Schlosser Mario | Director | S | 15,491 | $28.9500 | $448.46K |
| Jun 23, 2026 | Schlosser Mario | Director | C | 47,500 | – | – |
| Jun 23, 2026 | Schlosser Mario | Director | S | 102 | $30.0900 | $3.07K |
| Jun 23, 2026 | Schlosser Mario | Director | S | 33,592 | $29.5800 | $993.65K |
| Jun 23, 2026 | Schlosser Mario | Director | S | 16,306 | $28.9500 | $472.06K |
| Jun 23, 2026 | Schlosser Mario | Director | C | 50,000 | – | – |
| Jun 23, 2026 | Schlosser Mario | Director | S | 102 | $30.0900 | $3.07K |
| Jun 23, 2026 | Schlosser Mario | Director | S | 33,591 | $29.5800 | $993.62K |
| Jun 23, 2026 | Schlosser Mario | Director | S | 16,307 | $28.9500 | $472.09K |
| Jun 23, 2026 | Schlosser Mario | Director | C | 50,000 | – | – |
| Jun 23, 2026 | Schlosser Mario | Director | S | 1,799 | $30.0900 | $54.13K |
| Jun 23, 2026 | Schlosser Mario | Director | S | 591,213 | $29.5800 | $17.49M |
| Jun 23, 2026 | Schlosser Mario | Director | S | 286,988 | $28.9500 | $8.31M |
| Jun 23, 2026 | Schlosser Mario | Director | C | 880,000 | – | – |
| Jun 4, 2026 | WITTMAN VANESSA AMES | Director | A | 8,475 | $0.0000 | $0.00 |
| Jun 4, 2026 | Gassen William | Director | A | 8,475 | $0.0000 | $0.00 |
| Jun 4, 2026 | Sankaran Sid | Director | A | 8,475 | $0.0000 | $0.00 |
| Jun 4, 2026 | Lang Laura W | Director | A | 8,475 | $0.0000 | $0.00 |
| Jun 4, 2026 | Plouffe David | Director | A | 8,475 | $0.0000 | $0.00 |
| Jun 2, 2026 | Blackley Richard Scott | Chief Financial Officer | S | 8,977 | $22.4500 | $201.53K |
| Jun 2, 2026 | Blackley Richard Scott | Chief Financial Officer | S | 22,706 | $21.7400 | $493.63K |
| Jun 2, 2026 | Liang Janet | President, Oscar Insurance | S | 3,535 | $22.4500 | $79.36K |
| Jun 2, 2026 | Liang Janet | President, Oscar Insurance | S | 8,940 | $21.7400 | $194.35K |
| Jun 2, 2026 | Schlosser Mario | Director | S | 9,668 | $22.4500 | $217.05K |
| Jun 2, 2026 | Schlosser Mario | Director | S | 24,452 | $21.7400 | $531.59K |
| Jun 2, 2026 | Baltrus Victoria | Chief Accounting Officer | S | 432 | $22.4500 | $9.70K |
| Jun 2, 2026 | Baltrus Victoria | Chief Accounting Officer | S | 1,091 | $21.7400 | $23.72K |
| Jun 2, 2026 | McAnaney Adam | Chief Legal Officer | S | 2,794 | $22.4500 | $62.73K |
| Jun 2, 2026 | McAnaney Adam | Chief Legal Officer | S | 7,065 | $21.7400 | $153.59K |