| Insider Trading |
Relationship |
Date |
Transaction |
Cost |
#Shares |
Value ($) |
#Shares Total |
SEC Form 4 |
| WITTMAN VANESSA AMES | Director | Sep 18 '26 | Sale | 32.24 | 25,000 | 806,000 | 112,121 | Sep 22 04:20 PM | | WITTMAN VANESSA AMES | Officer | Sep 18 '26 | Proposed Sale | 32.24 | 25,000 | 806,000 | | Sep 18 04:02 PM | | Liang Janet | President, Oscar Insurance | Sep 03 '26 | Sale | 31.45 | 10,360 | 325,822 | 248,697 | Sep 08 04:22 PM | | Baltrus Victoria | Chief Accounting Officer | Sep 03 '26 | Sale | 31.45 | 958 | 30,129 | 213,631 | Sep 08 04:16 PM | | Blackley Richard Scott | Chief Financial Officer | Sep 03 '26 | Sale | 31.45 | 28,869 | 907,930 | 1,046,108 | Sep 08 04:16 PM | | McAnaney Adam | Chief Legal Officer | Sep 03 '26 | Sale | 31.45 | 9,092 | 285,943 | 209,004 | Sep 08 04:16 PM | | Schlosser Mario | Director | Sep 03 '26 | Sale | 31.45 | 31,422 | 988,222 | 449,444 | Sep 08 04:16 PM | | McAnaney Adam | Officer | Sep 03 '26 | Proposed Sale | 31.45 | 9,092 | 285,950 | | Sep 03 03:46 PM | | Schlosser Mario | Officer | Sep 03 '26 | Proposed Sale | 31.45 | 31,422 | 988,244 | | Sep 03 03:44 PM | | Liang Janet | Officer | Sep 03 '26 | Proposed Sale | 31.45 | 10,360 | 325,829 | | Sep 03 03:31 PM | | Blackley Richard Scott | Officer | Sep 03 '26 | Proposed Sale | 31.45 | 28,869 | 907,950 | | Sep 03 03:22 PM | | Schlosser Mario | Director | Aug 27 '26 | Sale | 30.34 | 600,000 | 18,204,000 | 480,866 | Aug 31 04:16 PM | | Schlosser Mario | Director | Aug 28 '26 | Sale | 30.79 | 150,000 | 4,618,500 | 480,866 | Aug 31 04:16 PM | | Schlosser Mario | Officer | Aug 28 '26 | Proposed Sale | 30.79 | 150,000 | 4,618,991 | | Aug 28 02:06 PM | | Schlosser Mario | Officer | Aug 27 '26 | Proposed Sale | 30.34 | 600,000 | 18,205,506 | | Aug 27 04:11 PM | | Blackley Richard Scott | Chief Financial Officer | Aug 18 '26 | Sale | 31.74 | 18,750 | 595,125 | 56,250 | Aug 20 04:16 PM | | JEFFERY H. BOYD | Former Affiliate | Aug 20 '26 | Proposed Sale | 33.15 | 288,514 | 9,564,297 | | Aug 20 04:08 PM | | Richard Scott Blackley | Officer - CFO | Aug 18 '26 | Proposed Sale | 32.76 | 18,750 | 614,250 | | Aug 18 04:56 PM | | JEFFERY H. BOYD | Former Affiliate | Aug 13 '26 | Proposed Sale | 30.11 | 288,513 | 8,687,790 | | Aug 13 04:08 PM | | BOYD JEFFERY H | Former Director | Aug 10 '26 | Proposed Sale | 28.13 | 116,666 | 3,281,655 | | Aug 10 04:40 PM | | JEFFERY H. BOYD | Former Affiliate | Aug 10 '26 | Proposed Sale | 28.27 | 134,370 | 3,799,231 | | Aug 10 04:11 PM | | Schlosser Mario | Director | Jul 01 '26 | Sale | 31.24 | 47,500 | 1,484,014 | 0 | Jul 06 04:11 PM | | Bertolini Mark T | Chief Executive Officer | Jun 29 '26 | Sale | 29.26 | 614,752 | 17,985,938 | 8,375,814 | Jul 01 04:16 PM | | Bertolini Mark T | Chief Executive Officer | Jun 30 '26 | Sale | 28.48 | 624,244 | 17,781,383 | 7,751,570 | Jul 01 04:16 PM | | Bertolini Mark T | Chief Executive Officer | Jun 25 '26 | Sale | 28.61 | 615,142 | 17,601,317 | 9,581,734 | Jun 29 04:17 PM | | Bertolini Mark T | Chief Executive Officer | Jun 26 '26 | Sale | 29.28 | 591,168 | 17,310,761 | 8,990,566 | Jun 29 04:17 PM | | Schlosser Mario | Director | Jun 23 '26 | Sale | 29.38 | 880,000 | 25,850,515 | 480,866 | Jun 25 04:17 PM | | Schlosser Mario | Director | Jun 23 '26 | Sale | 29.38 | 147,500 | 4,332,898 | 0 | Jun 25 04:17 PM | | Mark Bertolini | Director | Jun 25 '26 | Proposed Sale | 29.93 | 2,776,937 | 83,113,724 | | Jun 25 04:05 PM | | Siena Pizzo-Schlosser Dynasty | Director | Jun 23 '26 | Proposed Sale | 28.54 | 50,000 | 1,427,000 | | Jun 23 04:26 PM | | Noah Pizzo-Schlosser Dynasty T | Director | Jun 23 '26 | Proposed Sale | 28.54 | 50,000 | 1,427,000 | | Jun 23 04:25 PM | | MARIO SCHLOSSER | Director | Jun 23 '26 | Proposed Sale | 28.54 | 880,000 | 25,115,200 | | Jun 23 04:24 PM | | Pizzo-Schlosser Family Dynasty | Director | Jun 23 '26 | Proposed Sale | 28.54 | 95,000 | 2,711,300 | | Jun 23 04:24 PM | | Baltrus Victoria | Chief Accounting Officer | Jun 02 '26 | Sale | 21.94 | 1,523 | 33,417 | 214,589 | Jun 04 04:17 PM | | Schlosser Mario | Director | Jun 02 '26 | Sale | 21.94 | 34,120 | 748,633 | 480,866 | Jun 04 04:16 PM | | McAnaney Adam | Chief Legal Officer | Jun 02 '26 | Sale | 21.94 | 9,859 | 216,318 | 218,096 | Jun 04 04:16 PM | | Liang Janet | President, Oscar Insurance | Jun 02 '26 | Sale | 21.94 | 12,475 | 273,716 | 259,057 | Jun 04 04:16 PM | | Blackley Richard Scott | Chief Financial Officer | Jun 02 '26 | Sale | 21.94 | 31,683 | 695,162 | 1,074,977 | Jun 04 04:15 PM | | Richard Scott Blackley | CFO | Jun 02 '26 | Proposed Sale | 22.23 | 34,808 | 773,782 | | Jun 02 04:05 PM | | Adam McAnaney | Chief Legal Officer | Jun 02 '26 | Proposed Sale | 22.23 | 10,832 | 240,795 | | Jun 02 04:05 PM | | Mario Schlosser | Director | Jun 02 '26 | Proposed Sale | 22.23 | 37,488 | 833,358 | | Jun 02 04:05 PM | | Janet Liang | President, Oscar Insurance | Jun 02 '26 | Proposed Sale | 22.23 | 13,706 | 304,684 | | Jun 02 04:05 PM | | Blackley Richard Scott | Chief Financial Officer | May 18 '26 | Sale | 25.03 | 110,000 | 2,753,300 | 1,106,660 | May 20 04:17 PM | | RICHARD SCOTT BLACKLEY | Officer | May 18 '26 | Proposed Sale | 23.32 | 110,000 | 2,565,200 | | May 18 04:31 PM | | Blackley Richard Scott | Chief Financial Officer | May 14 '26 | Sale | 23.16 | 100,000 | 2,316,031 | 1,216,660 | May 18 04:15 PM | | RICHARD SCOTT BLACKLEY | Officer | May 14 '26 | Proposed Sale | 23.62 | 100,000 | 2,362,000 | | May 14 04:23 PM | | Bertolini Mark T | Chief Executive Officer | Apr 06 '26 | Buy | 11.92 | 1,000,000 | 11,920,000 | 10,196,876 | Apr 07 04:16 PM | | Liang Janet | President, Oscar Insurance | Mar 02 '26 | Sale | 13.39 | 7,453 | 99,796 | 271,532 | Mar 04 04:23 PM | | Baltrus Victoria | Chief Accounting Officer | Mar 02 '26 | Sale | 13.39 | 4,638 | 62,103 | 216,112 | Mar 04 04:19 PM | | McAnaney Adam | Chief Legal Officer | Mar 02 '26 | Sale | 13.39 | 18,710 | 250,527 | 227,955 | Mar 04 04:18 PM | | Schlosser Mario | President of Technology & CTO | Mar 02 '26 | Sale | 13.39 | 24,335 | 325,846 | 514,986 | Mar 04 04:17 PM | | Blackley Richard Scott | Chief Financial Officer | Mar 02 '26 | Sale | 13.39 | 19,221 | 257,369 | 1,466,660 | Mar 04 04:17 PM | | Blackley Richard Scott | Chief Financial Officer | Mar 02 '26 | Proposed Sale | 13.66 | 19,638 | 268,255 | | Mar 02 04:17 PM | | Schlosser Mario | Officer / Director | Mar 02 '26 | Proposed Sale | 13.66 | 20,629 | 281,792 | | Mar 02 04:05 PM | | Adam McAnaney | Chief Legal Officer | Mar 02 '26 | Proposed Sale | 13.66 | 15,530 | 212,140 | | Mar 02 04:05 PM | | Janet Liang | President, Oscar Insurance | Mar 02 '26 | Proposed Sale | 13.66 | 6,468 | 88,353 | | Mar 02 04:05 PM | | Schlosser Mario | President of Technology & CTO | Jan 08 '26 | Sale | 17.65 | 23,038 | 406,621 | 350,180 | Jan 12 04:18 PM | | Schlosser Mario | President of Technology & CTO | Jan 06 '26 | Sale | 17.01 | 76,962 | 1,309,124 | 350,180 | Jan 08 04:17 PM | | MARIO SCHLOSSER | Director | Jan 06 '26 | Proposed Sale | 16.57 | 100,000 | 1,657,000 | | Jan 06 04:31 PM | | Schlosser Mario | President of Technology & CTO | Jan 02 '26 | Sale | 15.02 | 137,933 | 2,071,754 | 360,215 | Jan 06 04:18 PM | | Schlosser Mario | President of Technology & CTO | Jan 05 '26 | Sale | 15.64 | 96,928 | 1,515,954 | 350,180 | Jan 06 04:18 PM | | MARIO SCHLOSSER | Director | Jan 02 '26 | Proposed Sale | 14.37 | 216,396 | 3,109,611 | | Jan 02 04:35 PM | | Schlosser Mario | President of Technology & CTO | Dec 24 '25 | Sale | 15.00 | 38,835 | 582,525 | 438,348 | Dec 30 04:16 PM | | MARIO SCHLOSSER | Director | Dec 24 '25 | Proposed Sale | 14.84 | 57,300 | 850,332 | | Dec 29 08:47 AM | | McAnaney Adam | Chief Legal Officer | Dec 02 '25 | Sale | 16.59 | 1,852 | 30,725 | 179,241 | Dec 04 04:17 PM | | Schlosser Mario | President of Technology & CTO | Dec 02 '25 | Sale | 16.59 | 23,965 | 397,579 | 477,183 | Dec 04 04:17 PM | | Liang Janet | President, Oscar Insurance | Dec 02 '25 | Sale | 16.59 | 7,338 | 121,737 | 172,527 | Dec 04 04:17 PM | | Blackley Richard Scott | Chief Financial Officer | Dec 02 '25 | Sale | 16.59 | 25,135 | 416,990 | 1,351,034 | Dec 04 04:16 PM | | Baltrus Victoria | Chief Accounting Officer | Dec 02 '25 | Sale | 16.59 | 4,149 | 68,832 | 203,450 | Dec 04 04:16 PM | | Blackley Richard Scott | Chief Financial Officer | Dec 02 '25 | Proposed Sale | 16.73 | 28,737 | 480,770 | | Dec 02 04:20 PM | | Janet Liang | President, Oscar Insurance | Dec 02 '25 | Proposed Sale | 16.73 | 8,398 | 140,499 | | Dec 02 04:18 PM | | Adam McAnaney | Chief Legal Officer | Dec 02 '25 | Proposed Sale | 16.73 | 2,123 | 35,518 | | Dec 02 04:17 PM | | Schlosser Mario | Officer / Director | Dec 02 '25 | Proposed Sale | 16.73 | 22,195 | 371,322 | | Dec 02 04:15 PM | | Schlosser Mario | President of Technology & CTO | Nov 11 '25 | Sale | 15.27 | 286,182 | 4,369,999 | 501,148 | Nov 13 04:18 PM | | Schlosser Mario | President of Technology & CTO | Nov 12 '25 | Sale | 15.05 | 105,300 | 1,584,765 | 501,148 | Nov 13 04:18 PM | | MARIO T SCHLOSSER | Officer | Nov 12 '25 | Proposed Sale | 15.05 | 105,300 | 1,585,134 | | Nov 12 04:17 PM | | MARIO T SCHLOSSER | Officer | Nov 11 '25 | Proposed Sale | 15.27 | 286,182 | 4,369,513 | | Nov 12 09:03 AM |
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