OSCR

Oscar Health, Inc.CIK 1568651 ☆ Sign in to watch Congress trades

Open-mkt buys · 90d

—

0 trades · 0 insiders

Open-mkt sales · 90d

$53.52M

18 trades · 6 insiders

Net · 90d

$-53.52M

Insiders on file

AI insights for OSCR PRO

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AI insights for OSCR

Insider sentiment score with a plain-English explanation, conviction score on every buy, and how the stock performed 30 and 90 days after past insider buys.

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Daily buy vs sell · 90 days

■ Open-market buys (P) ■ Open-market sales (S) · daily dollar value by transaction date

Insiders

Insider	Role	Trades	Bought	Sold	Last trade
Gassen William	Director	12	$0	$0	2026-10-08
Plouffe David	Director	13	$0	$0	2026-10-08
Sankaran Sid	Interim CFO	19	$0	$5.18M	2026-10-08
Thrive Partners II GP, LLC	Director, 10% Owner	13	$0	$0	2026-09-18
Thrive Partners III GP, LLC	Director, 10% Owner	13	$0	$0	2026-09-18
Kushner Joshua	Vice Chairman	61	$116.35M	$0	2026-09-18
WITTMAN VANESSA AMES	Director	8	$0	$1.61M	2026-09-18
Baltrus Victoria	Chief Accounting Officer	91	$0	$1.40M	2026-09-03
Liang Janet	President, Oscar Insurance	12	$0	$1.15M	2026-09-03
Schlosser Mario	President of Technology & CTO	120	$1.00M	$118.91M	2026-09-03
McAnaney Adam	Chief Legal Officer	12	$0	$1.07M	2026-09-03
Blackley Richard Scott	Chief Transformation Officer	128	$0	$16.71M	2026-09-03
Bertolini Mark T	Chief Executive Officer	19	$11.92M	$70.68M	2026-06-30
Lang Laura W	Director	5	$0	$0	2026-06-04
BOYD JEFFERY H	Director	23	$0	$0	2026-04-09
Robinson Elbert O. Jr.	Director	6	$0	$837.0K	2025-05-12
Quane Alessandrea C.	EVP, Chief Insurance Officer	110	$0	$7.50M	2024-12-06
Wolin Steven	Chief Operating Officer	44	$0	$1.07M	2024-12-02
Bopitiya Ranmali	EVP & Chief Legal Officer	62	$0	$3.25M	2024-12-02
Thrive Partners VII Growth GP, LLC	Director, 10% Owner	16	$58.76M	$0	2024-11-21
Thrive Capital Partners VII Growth, L.P.	Director, 10% Owner	9	$29.33M	$0	2024-11-14
Alphabet Inc.	10% Owner	3	$0	$52.52M	2023-08-17
Weaver Dennis	Chief Clinical Officer	35	$0	$1.41M	2022-12-02
PHILLIPS JR CHARLES E	Director	5	$0	$0	2022-10-14
Joyce Meghan V.	Chief Operating Officer	15	$0	$4.18M	2022-03-02
Thrive Partners VII GP, LLC	10% Owner	9	$28.26M	$0	2021-09-13
KLEIN JOEL	Chief Policy & Strat. Officer	4	$0	$2.95M	2021-08-18
Fischel Ari	VP, Finance & Accounting	2	$0	$259.8K	2021-03-05
List Teri	Director	1	$0	$0	2021-03-05

Trade history

Insider	Role	Code	Trade	Filed	Shares	Price	Value	Owned after
Plouffe David	Director	A Award deriv	2026-10-08	2026-10-13	641	$33.10	$21.2K	8,176	SEC↗
Sankaran Sid	Director	A Award deriv	2026-10-08	2026-10-13	1,472	$33.10	$48.7K	3,533	SEC↗
Gassen William	Director	A Award deriv	2026-10-08	2026-10-13	698	$33.10	$23.1K	7,769	SEC↗
Thrive Partners III GP, LLC	Director, 10% Owner	J Other deriv	2026-09-18	2026-09-18	6,268,097	—	$0	6,268,097	SEC↗
Thrive Partners III GP, LLC	Director, 10% Owner	J Other deriv	2026-09-18	2026-09-18	1,323,589	—	$0	4,779,730	SEC↗
Thrive Partners III GP, LLC	Director, 10% Owner	J Other deriv	2026-09-18	2026-09-18	75,520	—	$0	75,520	SEC↗
Thrive Partners III GP, LLC	Director, 10% Owner	J Other deriv	2026-09-18	2026-09-18	4,855,810	—	$0	17,535,258	SEC↗
Thrive Partners III GP, LLC	Director, 10% Owner	J Other deriv	2026-09-18	2026-09-18	164,218	—	$0	593,021	SEC↗
Kushner Joshua	Co-Founder and Vice Chairman	J Other deriv	2026-09-18	2026-09-18	1,323,589	—	$0	4,779,730	SEC↗
Kushner Joshua	Co-Founder and Vice Chairman	J Other deriv	2026-09-18	2026-09-18	164,218	—	$0	593,021	SEC↗
Kushner Joshua	Co-Founder and Vice Chairman	J Other deriv	2026-09-18	2026-09-18	6,268,097	—	$0	6,268,097	SEC↗
Kushner Joshua	Co-Founder and Vice Chairman	J Other deriv	2026-09-18	2026-09-18	75,520	—	$0	75,520	SEC↗
Kushner Joshua	Co-Founder and Vice Chairman	J Other deriv	2026-09-18	2026-09-18	4,855,810	—	$0	17,535,258	SEC↗
Thrive Partners III GP, LLC	Director, 10% Owner	J Other	2026-09-18	2026-09-18	164,218	—	$0	164,218	SEC↗
Thrive Partners III GP, LLC	Director, 10% Owner	J Other	2026-09-18	2026-09-18	1,323,589	—	$0	1,323,589	SEC↗
Thrive Partners III GP, LLC	Director, 10% Owner	J Other	2026-09-18	2026-09-18	75,520	—	$0	0	SEC↗
Thrive Partners III GP, LLC	Director, 10% Owner	J Other	2026-09-18	2026-09-18	6,268,097	—	$0	0	SEC↗
Thrive Partners III GP, LLC	Director, 10% Owner	J Other	2026-09-18	2026-09-18	4,855,810	—	$0	4,855,810	SEC↗
Thrive Partners III GP, LLC	Director, 10% Owner	J Other	2026-09-18	2026-09-18	1,323,589	—	$0	0	SEC↗
Thrive Partners III GP, LLC	Director, 10% Owner	J Other	2026-09-18	2026-09-18	4,855,810	—	$0	0	SEC↗
Thrive Partners III GP, LLC	Director, 10% Owner	J Other	2026-09-18	2026-09-18	164,218	—	$0	0	SEC↗
Kushner Joshua	Co-Founder and Vice Chairman	J Other	2026-09-18	2026-09-18	75,520	—	$0	0	SEC↗
Kushner Joshua	Co-Founder and Vice Chairman	J Other	2026-09-18	2026-09-18	4,855,810	—	$0	4,855,810	SEC↗
Kushner Joshua	Co-Founder and Vice Chairman	J Other	2026-09-18	2026-09-18	1,323,589	—	$0	1,323,589	SEC↗
Kushner Joshua	Co-Founder and Vice Chairman	J Other	2026-09-18	2026-09-18	6,268,097	—	$0	0	SEC↗
Kushner Joshua	Co-Founder and Vice Chairman	J Other	2026-09-18	2026-09-18	164,218	—	$0	164,218	SEC↗
Kushner Joshua	Co-Founder and Vice Chairman	J Other	2026-09-18	2026-09-18	164,218	—	$0	0	SEC↗
Kushner Joshua	Co-Founder and Vice Chairman	J Other	2026-09-18	2026-09-18	4,855,810	—	$0	0	SEC↗
Kushner Joshua	Co-Founder and Vice Chairman	J Other	2026-09-18	2026-09-18	1,323,589	—	$0	0	SEC↗
WITTMAN VANESSA AMES	Director	S Sale	2026-09-18	2026-09-22	25,000	$32.24	$806.0K	112,121	SEC↗
Kushner Joshua	Co-Founder and Vice Chairman	J Other deriv	2026-09-18	2026-09-18	75,520	—	$0	75,520	SEC↗
Kushner Joshua	Co-Founder and Vice Chairman	J Other deriv	2026-09-18	2026-09-18	6,268,097	—	$0	6,268,097	SEC↗
Kushner Joshua	Co-Founder and Vice Chairman	J Other deriv	2026-09-18	2026-09-18	164,218	—	$0	593,021	SEC↗
Kushner Joshua	Co-Founder and Vice Chairman	J Other deriv	2026-09-18	2026-09-18	4,855,810	—	$0	17,535,258	SEC↗
Kushner Joshua	Co-Founder and Vice Chairman	J Other deriv	2026-09-18	2026-09-18	1,323,589	—	$0	4,779,730	SEC↗
Kushner Joshua	Co-Founder and Vice Chairman	J Other	2026-09-18	2026-09-18	164,218	—	$0	0	SEC↗
Kushner Joshua	Co-Founder and Vice Chairman	J Other	2026-09-18	2026-09-18	4,855,810	—	$0	0	SEC↗
Kushner Joshua	Co-Founder and Vice Chairman	J Other	2026-09-18	2026-09-18	1,323,589	—	$0	0	SEC↗
Kushner Joshua	Co-Founder and Vice Chairman	J Other	2026-09-18	2026-09-18	164,218	—	$0	164,218	SEC↗
Kushner Joshua	Co-Founder and Vice Chairman	J Other	2026-09-18	2026-09-18	4,855,810	—	$0	4,855,810	SEC↗
Kushner Joshua	Co-Founder and Vice Chairman	J Other	2026-09-18	2026-09-18	1,323,589	—	$0	1,323,589	SEC↗
Kushner Joshua	Co-Founder and Vice Chairman	J Other	2026-09-18	2026-09-18	75,520	—	$0	0	SEC↗
Kushner Joshua	Co-Founder and Vice Chairman	J Other	2026-09-18	2026-09-18	6,268,097	—	$0	0	SEC↗
Thrive Partners II GP, LLC	Director, 10% Owner	J Other deriv	2026-09-18	2026-09-18	75,520	—	$0	75,520	SEC↗
Thrive Partners II GP, LLC	Director, 10% Owner	J Other deriv	2026-09-18	2026-09-18	6,268,097	—	$0	6,268,097	SEC↗
Thrive Partners II GP, LLC	Director, 10% Owner	J Other deriv	2026-09-18	2026-09-18	164,218	—	$0	593,021	SEC↗
Thrive Partners II GP, LLC	Director, 10% Owner	J Other deriv	2026-09-18	2026-09-18	4,855,810	—	$0	17,535,258	SEC↗
Thrive Partners II GP, LLC	Director, 10% Owner	J Other deriv	2026-09-18	2026-09-18	1,323,589	—	$0	4,779,730	SEC↗
Thrive Partners II GP, LLC	Director, 10% Owner	J Other	2026-09-18	2026-09-18	164,218	—	$0	0	SEC↗
Thrive Partners II GP, LLC	Director, 10% Owner	J Other	2026-09-18	2026-09-18	4,855,810	—	$0	0	SEC↗
Thrive Partners II GP, LLC	Director, 10% Owner	J Other	2026-09-18	2026-09-18	1,323,589	—	$0	0	SEC↗
Thrive Partners II GP, LLC	Director, 10% Owner	J Other	2026-09-18	2026-09-18	164,218	—	$0	164,218	SEC↗
Thrive Partners II GP, LLC	Director, 10% Owner	J Other	2026-09-18	2026-09-18	4,855,810	—	$0	4,855,810	SEC↗
Thrive Partners II GP, LLC	Director, 10% Owner	J Other	2026-09-18	2026-09-18	1,323,589	—	$0	1,323,589	SEC↗
Thrive Partners II GP, LLC	Director, 10% Owner	J Other	2026-09-18	2026-09-18	75,520	—	$0	0	SEC↗
Thrive Partners II GP, LLC	Director, 10% Owner	J Other	2026-09-18	2026-09-18	6,268,097	—	$0	0	SEC↗
WITTMAN VANESSA AMES	Director	S Sale	2026-09-18	2026-09-22	25,000	$32.24	$806.0K	112,121	SEC↗
Schlosser Mario	Director	S Sale	2026-09-03	2026-09-08	31,422	$31.45	$988.2K	449,444	SEC↗
McAnaney Adam	Chief Legal Officer	S Sale	2026-09-03	2026-09-08	9,092	$31.45	$285.9K	209,004	SEC↗
Blackley Richard Scott	Chief Financial Officer	S Sale	2026-09-03	2026-09-08	28,869	$31.45	$907.9K	1,046,108	SEC↗
Baltrus Victoria	Chief Accounting Officer	S Sale	2026-09-03	2026-09-08	958	$31.45	$30.1K	213,631	SEC↗
Liang Janet	President, Oscar Insurance	S Sale	2026-09-03	2026-09-08	10,360	$31.45	$325.8K	248,697	SEC↗
Schlosser Mario	Director	S Sale	2026-09-03	2026-09-08	31,422	$31.45	$988.2K	449,444	SEC↗
McAnaney Adam	Chief Legal Officer	S Sale	2026-09-03	2026-09-08	9,092	$31.45	$285.9K	209,004	SEC↗
Liang Janet	President, Oscar Insurance	S Sale	2026-09-03	2026-09-08	10,360	$31.45	$325.8K	248,697	SEC↗
Blackley Richard Scott	Chief Financial Officer	S Sale	2026-09-03	2026-09-08	28,869	$31.45	$907.9K	1,046,108	SEC↗
Baltrus Victoria	Chief Accounting Officer	S Sale	2026-09-03	2026-09-08	958	$31.45	$30.1K	213,631	SEC↗
Schlosser Mario	Director	C Conversion deriv	2026-08-28	2026-08-31	150,000	—	$0	1,212,293	SEC↗
Schlosser Mario	Director	M Exercise deriv	2026-08-28	2026-08-31	150,000	—	$0	2,990,000	SEC↗
Schlosser Mario	Director	M Exercise deriv	2026-08-28	2026-08-31	150,000	$9.75	$1.46M	1,362,293	SEC↗
Schlosser Mario	Director	S Sale	2026-08-28	2026-08-31	150,000	$30.79	$4.62M	480,866	SEC↗
Schlosser Mario	Director	C Conversion	2026-08-28	2026-08-31	150,000	—	$0	630,866	SEC↗
Schlosser Mario	Director	C Conversion deriv	2026-08-28	2026-08-31	150,000	—	$0	1,212,293	SEC↗
Schlosser Mario	Director	M Exercise deriv	2026-08-28	2026-08-31	150,000	$9.75	$1.46M	1,362,293	SEC↗
Schlosser Mario	Director	M Exercise deriv	2026-08-28	2026-08-31	150,000	—	$0	2,990,000	SEC↗
Schlosser Mario	Director	S Sale	2026-08-28	2026-08-31	150,000	$30.79	$4.62M	480,866	SEC↗
Schlosser Mario	Director	C Conversion	2026-08-28	2026-08-31	150,000	—	—	630,866	SEC↗
Schlosser Mario	Director	M Exercise deriv	2026-08-27	2026-08-31	600,000	—	$0	3,140,000	SEC↗
Schlosser Mario	Director	M Exercise deriv	2026-08-27	2026-08-31	600,000	$9.75	$5.85M	1,812,293	SEC↗
Schlosser Mario	Director	C Conversion deriv	2026-08-27	2026-08-31	600,000	—	$0	1,212,293	SEC↗
Schlosser Mario	Director	S Sale	2026-08-27	2026-08-31	600,000	$30.34	$18.20M	480,866	SEC↗
Schlosser Mario	Director	C Conversion	2026-08-27	2026-08-31	600,000	—	$0	1,080,866	SEC↗
Schlosser Mario	Director	C Conversion deriv	2026-08-27	2026-08-31	600,000	—	$0	1,212,293	SEC↗
Schlosser Mario	Director	M Exercise deriv	2026-08-27	2026-08-31	600,000	$9.75	$5.85M	1,812,293	SEC↗
Schlosser Mario	Director	M Exercise deriv	2026-08-27	2026-08-31	600,000	—	$0	3,140,000	SEC↗
Schlosser Mario	Director	S Sale	2026-08-27	2026-08-31	600,000	$30.34	$18.20M	480,866	SEC↗
Schlosser Mario	Director	C Conversion	2026-08-27	2026-08-31	600,000	—	—	1,080,866	SEC↗
Blackley Richard Scott	Chief Financial Officer	S Sale	2026-08-18	2026-08-20	18,750	$31.74	$595.1K	56,250	SEC↗
Blackley Richard Scott	Chief Financial Officer	S Sale	2026-08-18	2026-08-20	18,750	$31.74	$595.1K	56,250	SEC↗
Plouffe David	Director	A Award deriv	2026-07-09	2026-07-13	681	$31.20	$21.2K	7,535	SEC↗
Sankaran Sid	Director	A Award deriv	2026-07-09	2026-07-13	858	$31.20	$26.8K	2,061	SEC↗
Gassen William	Director	A Award deriv	2026-07-09	2026-07-13	684	$31.20	$21.3K	7,071	SEC↗
Schlosser Mario	Director	C Conversion deriv	2026-07-01	2026-07-06	47,500	—	$0	538,333	SEC↗
Schlosser Mario	Director	S Sale	2026-07-01	2026-07-06	30,228	$31.65	$956.7K	0	SEC↗
Schlosser Mario	Director	S Sale	2026-07-01	2026-07-06	13,672	$30.80	$421.1K	30,228	SEC↗
Schlosser Mario	Director	S Sale	2026-07-01	2026-07-06	3,600	$29.50	$106.2K	43,900	SEC↗
Schlosser Mario	Director	C Conversion	2026-07-01	2026-07-06	47,500	—	$0	47,500	SEC↗
Bertolini Mark T	Chief Executive Officer	S Sale	2026-06-30	2026-07-01	135,590	$28.97	$3.93M	7,751,570	SEC↗
Bertolini Mark T	Chief Executive Officer	S Sale	2026-06-30	2026-07-01	488,654	$28.35	$13.85M	7,887,160	SEC↗
Bertolini Mark T	Chief Executive Officer	S Sale	2026-06-29	2026-07-01	555,826	$29.17	$16.21M	8,434,740	SEC↗
Bertolini Mark T	Chief Executive Officer	S Sale	2026-06-29	2026-07-01	58,926	$30.08	$1.77M	8,375,814	SEC↗
Bertolini Mark T	Chief Executive Officer	S Sale	2026-06-26	2026-06-29	441,373	$29.11	$12.85M	9,140,361	SEC↗
Bertolini Mark T	Chief Executive Officer	S Sale	2026-06-26	2026-06-29	149,795	$29.79	$4.46M	8,990,566	SEC↗
Bertolini Mark T	Chief Executive Officer	S Sale	2026-06-25	2026-06-29	17,200	$29.08	$500.2K	9,581,734	SEC↗
Bertolini Mark T	Chief Executive Officer	S Sale	2026-06-25	2026-06-29	597,942	$28.60	$17.10M	9,598,934	SEC↗
Schlosser Mario	Director	C Conversion deriv	2026-06-23	2026-06-25	880,000	—	$0	1,212,293	SEC↗
Schlosser Mario	Director	C Conversion deriv	2026-06-23	2026-06-25	50,000	—	$0	283,333	SEC↗
Schlosser Mario	Director	C Conversion deriv	2026-06-23	2026-06-25	50,000	—	$0	283,333	SEC↗
Schlosser Mario	Director	M Exercise deriv	2026-06-23	2026-06-25	660,000	—	$0	3,740,000	SEC↗
Schlosser Mario	Director	M Exercise deriv	2026-06-23	2026-06-25	660,000	$9.75	$6.43M	2,092,293	SEC↗
Schlosser Mario	Director	C Conversion deriv	2026-06-23	2026-06-25	47,500	—	$0	585,833	SEC↗
Schlosser Mario	Director	S Sale	2026-06-23	2026-06-25	33,591	$29.58	$993.6K	102	SEC↗
Schlosser Mario	Director	C Conversion	2026-06-23	2026-06-25	880,000	—	$0	1,360,866	SEC↗
Schlosser Mario	Director	S Sale	2026-06-23	2026-06-25	286,988	$28.95	$8.31M	1,073,878	SEC↗
Schlosser Mario	Director	S Sale	2026-06-23	2026-06-25	31,912	$29.58	$944.0K	97	SEC↗
Schlosser Mario	Director	S Sale	2026-06-23	2026-06-25	15,491	$28.95	$448.5K	32,009	SEC↗
Schlosser Mario	Director	C Conversion	2026-06-23	2026-06-25	47,500	—	$0	47,500	SEC↗
Schlosser Mario	Director	S Sale	2026-06-23	2026-06-25	102	$30.09	$3.1K	0	SEC↗
Schlosser Mario	Director	S Sale	2026-06-23	2026-06-25	33,592	$29.58	$993.7K	102	SEC↗
Schlosser Mario	Director	S Sale	2026-06-23	2026-06-25	16,306	$28.95	$472.1K	33,694	SEC↗
Schlosser Mario	Director	C Conversion	2026-06-23	2026-06-25	50,000	—	$0	50,000	SEC↗
Schlosser Mario	Director	S Sale	2026-06-23	2026-06-25	102	$30.09	$3.1K	0	SEC↗
Schlosser Mario	Director	S Sale	2026-06-23	2026-06-25	97	$30.09	$2.9K	0	SEC↗
Schlosser Mario	Director	S Sale	2026-06-23	2026-06-25	16,307	$28.95	$472.1K	33,693	SEC↗
Schlosser Mario	Director	C Conversion	2026-06-23	2026-06-25	50,000	—	$0	50,000	SEC↗
Schlosser Mario	Director	S Sale	2026-06-23	2026-06-25	1,799	$30.09	$54.1K	480,866	SEC↗
Schlosser Mario	Director	S Sale	2026-06-23	2026-06-25	591,213	$29.58	$17.49M	482,665	SEC↗
WITTMAN VANESSA AMES	Director	A Award	2026-06-04	2026-06-08	8,475	—	$0	137,121	SEC↗
Gassen William	Director	A Award	2026-06-04	2026-06-08	8,475	—	$0	82,840	SEC↗
Sankaran Sid	Director	A Award	2026-06-04	2026-06-08	8,475	—	$0	22,609	SEC↗
Plouffe David	Director	A Award	2026-06-04	2026-06-08	8,475	—	$0	137,121	SEC↗
Lang Laura W	Director	A Award	2026-06-04	2026-06-08	8,475	—	$0	82,840	SEC↗
Blackley Richard Scott	Chief Financial Officer	S Sale	2026-06-02	2026-06-04	22,706	$21.74	$493.6K	1,083,954	SEC↗
Blackley Richard Scott	Chief Financial Officer	S Sale	2026-06-02	2026-06-04	8,977	$22.45	$201.5K	1,074,977	SEC↗
Liang Janet	President, Oscar Insurance	S Sale	2026-06-02	2026-06-04	3,535	$22.45	$79.4K	259,057	SEC↗
Liang Janet	President, Oscar Insurance	S Sale	2026-06-02	2026-06-04	8,940	$21.74	$194.4K	262,592	SEC↗
McAnaney Adam	Chief Legal Officer	S Sale	2026-06-02	2026-06-04	2,794	$22.45	$62.7K	218,096	SEC↗
McAnaney Adam	Chief Legal Officer	S Sale	2026-06-02	2026-06-04	7,065	$21.74	$153.6K	220,890	SEC↗
Schlosser Mario	Director	S Sale	2026-06-02	2026-06-04	9,668	$22.45	$217.0K	480,866	SEC↗
Schlosser Mario	Director	S Sale	2026-06-02	2026-06-04	24,452	$21.74	$531.6K	490,534	SEC↗
Baltrus Victoria	Chief Accounting Officer	S Sale	2026-06-02	2026-06-04	1,091	$21.74	$23.7K	215,021	SEC↗
Baltrus Victoria	Chief Accounting Officer	S Sale	2026-06-02	2026-06-04	432	$22.45	$9.7K	214,589	SEC↗
Blackley Richard Scott	Chief Financial Officer	S Sale	2026-05-18	2026-05-20	110,000	$25.03	$2.75M	1,106,660	SEC↗
Blackley Richard Scott	Chief Financial Officer	S Sale	2026-05-14	2026-05-18	8,741	$23.79	$207.9K	1,216,660	SEC↗
Blackley Richard Scott	Chief Financial Officer	S Sale	2026-05-14	2026-05-18	91,259	$23.10	$2.11M	1,225,401	SEC↗
Plouffe David	Director	A Award deriv	2026-04-09	2026-04-13	1,461	$14.54	$21.2K	6,854	SEC↗
BOYD JEFFERY H	Director	A Award deriv	2026-04-09	2026-04-13	3,610	$14.54	$52.5K	69,858	SEC↗
Gassen William	Director	A Award deriv	2026-04-09	2026-04-13	1,418	$14.54	$20.6K	6,387	SEC↗
Sankaran Sid	Director	A Award deriv	2026-04-09	2026-04-13	1,203	$14.54	$17.5K	1,203	SEC↗
Bertolini Mark T	Chief Executive Officer	P Buy	2026-04-06	2026-04-07	1,000,000	$11.92	$11.92M	10,196,876	SEC↗
Bertolini Mark T	Chief Executive Officer	F Tax w/h	2026-04-06	2026-04-07	1,000,001	$11.92	$11.92M	9,196,876	SEC↗
Bertolini Mark T	Chief Executive Officer	M Exercise deriv	2026-04-03	2026-04-07	5,733,334	—	$0	0	SEC↗
Bertolini Mark T	Chief Executive Officer	M Exercise	2026-04-03	2026-04-07	5,733,334	—	$0	10,196,877	SEC↗
Blackley Richard Scott	Chief Financial Officer	G Gift	2026-03-12	2026-03-16	75,000	—	$0	75,000	SEC↗
Blackley Richard Scott	Chief Financial Officer	G Gift	2026-03-12	2026-03-16	75,000	—	$0	1,391,660	SEC↗
Blackley Richard Scott	Chief Financial Officer	G Gift	2026-03-12	2026-03-16	75,000	—	$0	1,316,660	SEC↗
Blackley Richard Scott	Chief Financial Officer	A Award	2026-03-02	2026-03-04	134,847	—	$0	1,485,881	SEC↗
Blackley Richard Scott	Chief Financial Officer	S Sale	2026-03-02	2026-03-04	19,221	$13.39	$257.4K	1,466,660	SEC↗
Schlosser Mario	President of Technology & CT	S Sale	2026-03-02	2026-03-04	24,335	$13.39	$325.8K	514,986	SEC↗
Schlosser Mario	President of Technology & CT	A Award	2026-03-02	2026-03-04	189,141	—	$0	539,321	SEC↗
McAnaney Adam	Chief Legal Officer	A Award	2026-03-02	2026-03-04	67,424	—	$0	246,665	SEC↗
McAnaney Adam	Chief Legal Officer	S Sale	2026-03-02	2026-03-04	18,710	$13.39	$250.5K	227,955	SEC↗
Baltrus Victoria	Chief Accounting Officer	A Award	2026-03-02	2026-03-04	17,300	—	$0	220,750	SEC↗
Baltrus Victoria	Chief Accounting Officer	S Sale	2026-03-02	2026-03-04	4,638	$13.39	$62.1K	216,112	SEC↗
Bertolini Mark T	Chief Executive Officer	A Award	2026-03-02	2026-03-04	1,596,877	—	$0	4,463,543	SEC↗
Liang Janet	President, Oscar Insurance	A Award	2026-03-02	2026-03-04	106,458	—	$0	278,985	SEC↗
Liang Janet	President, Oscar Insurance	S Sale	2026-03-02	2026-03-04	7,453	$13.39	$99.8K	271,532	SEC↗
Schlosser Mario	President of Technology & CT	C Conversion deriv	2026-01-08	2026-01-12	23,038	—	$0	1,432,293	SEC↗
Plouffe David	Director	A Award deriv	2026-01-08	2026-01-12	1,257	$16.90	$21.2K	5,393	SEC↗
Gassen William	Director	A Award deriv	2026-01-08	2026-01-12	1,220	$16.90	$20.6K	4,969	SEC↗
BOYD JEFFERY H	Director	A Award deriv	2026-01-08	2026-01-12	3,106	$16.90	$52.5K	66,248	SEC↗
Schlosser Mario	President of Technology & CT	S Sale	2026-01-08	2026-01-12	23,038	$17.65	$406.6K	350,180	SEC↗
Schlosser Mario	President of Technology & CT	C Conversion	2026-01-08	2026-01-12	23,038	—	$0	373,218	SEC↗
Schlosser Mario	President of Technology & CT	C Conversion deriv	2026-01-06	2026-01-08	76,962	—	$0	1,455,331	SEC↗
Schlosser Mario	President of Technology & CT	S Sale	2026-01-06	2026-01-08	76,962	$17.01	$1.31M	350,180	SEC↗
Schlosser Mario	President of Technology & CT	C Conversion	2026-01-06	2026-01-08	76,962	—	$0	427,142	SEC↗
Schlosser Mario	President of Technology & CT	C Conversion deriv	2026-01-05	2026-01-06	86,893	—	$0	1,532,293	SEC↗
Schlosser Mario	President of Technology & CT	C Conversion	2026-01-05	2026-01-06	86,893	—	$0	447,108	SEC↗
Schlosser Mario	President of Technology & CT	S Sale	2026-01-05	2026-01-06	96,928	$15.64	$1.52M	350,180	SEC↗
Schlosser Mario	President of Technology & CT	C Conversion deriv	2026-01-02	2026-01-06	59,800	—	$0	1,619,186	SEC↗
Schlosser Mario	President of Technology & CT	C Conversion	2026-01-02	2026-01-06	59,800	—	$0	498,148	SEC↗
Schlosser Mario	President of Technology & CT	S Sale	2026-01-02	2026-01-06	137,933	$15.02	$2.07M	360,215	SEC↗
Schlosser Mario	President of Technology & CT	S Sale	2025-12-24	2025-12-30	38,835	$15.00	$582.5K	438,348	SEC↗
Baltrus Victoria	Chief Accounting Officer	S Sale	2025-12-02	2025-12-04	4,149	$16.59	$68.8K	203,450	SEC↗
Blackley Richard Scott	Chief Financial Officer	S Sale	2025-12-02	2025-12-04	25,135	$16.59	$417.0K	1,351,034	SEC↗
Liang Janet	President, Oscar Insurance	S Sale	2025-12-02	2025-12-04	7,338	$16.59	$121.7K	172,527	SEC↗
Schlosser Mario	President of Technology & CT	S Sale	2025-12-02	2025-12-04	23,965	$16.59	$397.6K	477,183	SEC↗
McAnaney Adam	Chief Legal Officer	S Sale	2025-12-02	2025-12-04	1,852	$16.59	$30.7K	179,241	SEC↗
Schlosser Mario	President of Technology & CT	C Conversion deriv	2025-11-12	2025-11-13	105,300	—	$0	1,678,986	SEC↗
Schlosser Mario	President of Technology & CT	M Exercise deriv	2025-11-12	2025-11-13	141,330	$6.36	$898.9K	1,784,286	SEC↗
Schlosser Mario	President of Technology & CT	M Exercise deriv	2025-11-12	2025-11-13	141,330	—	$0	0	SEC↗
Schlosser Mario	President of Technology & CT	S Sale	2025-11-12	2025-11-13	105,300	$15.05	$1.58M	501,148	SEC↗
Schlosser Mario	President of Technology & CT	C Conversion	2025-11-12	2025-11-13	105,300	—	$0	606,448	SEC↗
Schlosser Mario	President of Technology & CT	M Exercise deriv	2025-11-11	2025-11-13	413,835	—	$0	141,330	SEC↗
Schlosser Mario	President of Technology & CT	C Conversion deriv	2025-11-11	2025-11-13	286,182	—	$0	1,642,956	SEC↗
Schlosser Mario	President of Technology & CT	M Exercise deriv	2025-11-11	2025-11-13	413,835	$6.36	$2.63M	1,929,138	SEC↗
Schlosser Mario	President of Technology & CT	C Conversion	2025-11-11	2025-11-13	286,182	—	$0	787,330	SEC↗
Schlosser Mario	President of Technology & CT	S Sale	2025-11-11	2025-11-13	286,182	$15.27	$4.37M	501,148	SEC↗
BOYD JEFFERY H	Director	A Award deriv	2025-10-09	2025-10-14	2,555	$20.54	$52.5K	63,142	SEC↗
Plouffe David	Director	A Award deriv	2025-10-09	2025-10-14	1,034	$20.54	$21.2K	4,136	SEC↗
Gassen William	Director	A Award deriv	2025-10-09	2025-10-14	1,004	$20.54	$20.6K	3,749	SEC↗
Schlosser Mario	President of Technology & CT	C Conversion deriv	2025-09-22	2025-09-24	395,000	—	$0	1,515,303	SEC↗
Schlosser Mario	President of Technology & CT	M Exercise deriv	2025-09-22	2025-09-24	555,165	$6.36	$3.53M	1,910,303	SEC↗
Schlosser Mario	President of Technology & CT	M Exercise deriv	2025-09-22	2025-09-24	555,165	—	$0	555,165	SEC↗
Schlosser Mario	President of Technology & CT	S Sale	2025-09-22	2025-09-24	395,000	$18.43	$7.28M	501,148	SEC↗
Schlosser Mario	President of Technology & CT	C Conversion	2025-09-22	2025-09-24	395,000	—	$0	896,148	SEC↗
Schlosser Mario	President of Technology & CT	F Tax w/h	2025-09-02	2025-09-04	23,879	$16.66	$397.8K	501,148	SEC↗
McAnaney Adam	Chief Legal Officer	F Tax w/h	2025-09-02	2025-09-04	1,845	$16.66	$30.7K	181,093	SEC↗
Liang Janet	President, Oscar Insurance	F Tax w/h	2025-09-02	2025-09-04	7,303	$16.66	$121.7K	179,865	SEC↗
Blackley Richard Scott	Chief Financial Officer	F Tax w/h	2025-09-02	2025-09-04	28,166	$16.66	$469.2K	1,376,169	SEC↗
Baltrus Victoria	Chief Accounting Officer	F Tax w/h	2025-09-02	2025-09-04	6,266	$16.66	$104.4K	207,599	SEC↗
BOYD JEFFERY H	Director	A Award deriv	2025-07-10	2025-07-14	3,380	$15.53	$52.5K	60,587	SEC↗
Gassen William	Director	A Award deriv	2025-07-10	2025-07-14	1,215	$15.53	$18.9K	2,745	SEC↗
Plouffe David	Director	A Award deriv	2025-07-10	2025-07-14	1,368	$15.53	$21.2K	3,102	SEC↗
Gassen William	Director	A Award	2025-06-04	2025-06-06	14,134	—	$0	74,365	SEC↗
Sankaran Sid	Director	A Award	2025-06-04	2025-06-06	14,134	—	$0	14,134	SEC↗
WITTMAN VANESSA AMES	Director	A Award	2025-06-04	2025-06-06	14,134	—	$0	128,646	SEC↗
Plouffe David	Director	A Award	2025-06-04	2025-06-06	14,134	—	$0	128,646	SEC↗
Lang Laura W	Director	A Award	2025-06-04	2025-06-06	14,134	—	$0	74,365	SEC↗
BOYD JEFFERY H	Director	A Award	2025-06-04	2025-06-06	14,134	—	$0	705,673	SEC↗
Baltrus Victoria	Chief Accounting Officer	F Tax w/h	2025-06-02	2025-06-04	6,265	$13.80	$86.5K	213,865	SEC↗
Blackley Richard Scott	Chief Financial Officer	F Tax w/h	2025-06-02	2025-06-04	28,185	$13.80	$389.0K	1,404,335	SEC↗
Schlosser Mario	President of Technology & CT	F Tax w/h	2025-06-02	2025-06-04	23,879	$13.80	$329.5K	525,027	SEC↗
Liang Janet	President, Oscar Insurance	F Tax w/h	2025-06-02	2025-06-04	7,196	$13.80	$99.3K	187,168	SEC↗
McAnaney Adam	Chief Legal Officer	F Tax w/h	2025-06-02	2025-06-04	1,847	$13.80	$25.5K	182,938	SEC↗
Robinson Elbert O. Jr.	Director	S Sale	2025-05-12	2025-05-14	25,000	$16.43	$410.8K	64,512	SEC↗
BOYD JEFFERY H	Director	A Award deriv	2025-04-10	2025-04-14	4,285	$12.25	$52.5K	57,207	SEC↗
Gassen William	Director	A Award deriv	2025-04-10	2025-04-14	1,530	$12.25	$18.7K	1,530	SEC↗
Plouffe David	Director	A Award deriv	2025-04-10	2025-04-14	1,734	$12.25	$21.2K	1,734	SEC↗
Bertolini Mark T	Chief Executive Officer	M Exercise deriv	2025-04-03	2025-04-07	955,556	—	$0	0	SEC↗
Bertolini Mark T	Chief Executive Officer	M Exercise	2025-04-03	2025-04-07	955,556	—	$0	2,866,666	SEC↗
McAnaney Adam	Chief Legal Officer	A Award	2025-03-05	2025-03-07	61,409	—	$0	184,785	SEC↗
Liang Janet	President, Oscar Insurance	A Award	2025-03-05	2025-03-07	96,962	—	$0	194,364	SEC↗
Blackley Richard Scott	Chief Financial Officer	A Award	2025-03-05	2025-03-07	103,426	—	$0	1,432,520	SEC↗
Schlosser Mario	President of Technology & CT	A Award	2025-03-05	2025-03-07	172,269	—	$0	375,966	SEC↗
Baltrus Victoria	Chief Accounting Officer	A Award	2025-03-05	2025-03-07	10,611	—	$0	220,130	SEC↗
Baltrus Victoria	Chief Accounting Officer	F Tax w/h	2025-03-01	2025-03-04	5,084	$14.61	$74.3K	209,519	SEC↗
Blackley Richard Scott	Chief Financial Officer	F Tax w/h	2025-03-01	2025-03-04	22,428	$14.61	$327.7K	1,329,094	SEC↗
Schlosser Mario	President of Technology & CT	F Tax w/h	2025-03-01	2025-03-04	7,970	$14.61	$116.4K	203,697	SEC↗
Liang Janet	President, Oscar Insurance	A Award deriv	2025-02-24	2025-02-26	147,637	—	$0	147,637	SEC↗
McAnaney Adam	Chief Legal Officer	A Award deriv	2025-02-24	2025-02-26	185,004	—	$0	185,004	SEC↗
Liang Janet	President, Oscar Insurance	A Award	2025-02-24	2025-02-26	97,402	—	$0	97,402	SEC↗
McAnaney Adam	Chief Legal Officer	A Award	2025-02-24	2025-02-26	123,376	—	$0	123,376	SEC↗
Sankaran Sid	Director	G Gift	2025-02-07	2025-02-11	295,687	—	$0	0	SEC↗
Sankaran Sid	Director	G Gift	2025-02-07	2025-02-11	295,687	—	$0	795,686	SEC↗
BOYD JEFFERY H	Director	A Award deriv	2025-01-09	2025-01-13	2,043	$15.29	$31.2K	52,922	SEC↗
Blackley Richard Scott	Chief Financial Officer	S Sale	2024-12-06	2024-12-09	11,423	$16.52	$188.7K	914,402	SEC↗
Blackley Richard Scott	Chief Financial Officer	S Sale	2024-12-06	2024-12-09	18,516	$15.93	$295.0K	925,825	SEC↗
Quane Alessandrea C.	EVP, Chief Insurance Officer	S Sale	2024-12-06	2024-12-09	6,408	$16.52	$105.9K	430,216	SEC↗
Quane Alessandrea C.	EVP, Chief Insurance Officer	S Sale	2024-12-06	2024-12-09	10,385	$15.93	$165.4K	436,624	SEC↗
Blackley Richard Scott	Chief Financial Officer	M Exercise deriv	2024-12-05	2024-12-09	62,500	—	$0	0	SEC↗
Quane Alessandrea C.	EVP, Chief Insurance Officer	M Exercise deriv	2024-12-05	2024-12-09	31,250	—	$0	0	SEC↗
Blackley Richard Scott	Chief Financial Officer	M Exercise	2024-12-05	2024-12-09	62,500	—	$0	944,341	SEC↗
Quane Alessandrea C.	EVP, Chief Insurance Officer	M Exercise	2024-12-05	2024-12-09	31,250	—	$0	447,009	SEC↗
Baltrus Victoria	Chief Accounting Officer	S Sale	2024-12-02	2024-12-03	7,933	$18.07	$143.3K	146,181	SEC↗
Baltrus Victoria	Chief Accounting Officer	S Sale	2024-12-02	2024-12-03	145	$18.48	$2.7K	146,036	SEC↗
Blackley Richard Scott	Chief Financial Officer	S Sale	2024-12-02	2024-12-03	456	$18.48	$8.4K	881,841	SEC↗
Blackley Richard Scott	Chief Financial Officer	S Sale	2024-12-02	2024-12-03	24,823	$18.07	$448.6K	882,297	SEC↗
Quane Alessandrea C.	EVP, Chief Insurance Officer	S Sale	2024-12-02	2024-12-03	26,411	$18.07	$477.2K	416,243	SEC↗
Quane Alessandrea C.	EVP, Chief Insurance Officer	S Sale	2024-12-02	2024-12-03	484	$18.48	$8.9K	415,759	SEC↗
Bopitiya Ranmali	EVP & Chief Legal Officer	S Sale	2024-12-02	2024-12-03	345	$18.48	$6.4K	241,488	SEC↗
Bopitiya Ranmali	EVP & Chief Legal Officer	S Sale	2024-12-02	2024-12-03	18,812	$18.07	$339.9K	241,833	SEC↗
Schlosser Mario	President of Technology & CT	S Sale	2024-12-02	2024-12-03	117	$18.48	$2.2K	81,962	SEC↗
Schlosser Mario	President of Technology & CT	S Sale	2024-12-02	2024-12-03	6,399	$18.07	$115.6K	82,079	SEC↗
Wolin Steven	Chief Operating Officer	S Sale	2024-12-02	2024-12-03	19,227	$18.07	$347.4K	102,951	SEC↗
Wolin Steven	Chief Operating Officer	S Sale	2024-12-02	2024-12-03	353	$18.48	$6.5K	102,598	SEC↗
Baltrus Victoria	Chief Accounting Officer	M Exercise deriv	2024-12-01	2024-12-03	888	—	$0	7,989	SEC↗
Baltrus Victoria	Chief Accounting Officer	M Exercise deriv	2024-12-01	2024-12-03	7,500	—	$0	37,498	SEC↗
Baltrus Victoria	Chief Accounting Officer	M Exercise deriv	2024-12-01	2024-12-03	4,120	—	$0	4,121	SEC↗
Baltrus Victoria	Chief Accounting Officer	M Exercise deriv	2024-12-01	2024-12-03	4,810	—	$0	14,433	SEC↗
Blackley Richard Scott	Chief Financial Officer	M Exercise deriv	2024-12-01	2024-12-03	7,015	—	$0	21,048	SEC↗
Blackley Richard Scott	Chief Financial Officer	M Exercise deriv	2024-12-01	2024-12-03	37,577	—	$0	338,200	SEC↗
Blackley Richard Scott	Chief Financial Officer	M Exercise deriv	2024-12-01	2024-12-03	8,653	—	$0	77,872	SEC↗
Quane Alessandrea C.	EVP, Chief Insurance Officer	M Exercise deriv	2024-12-01	2024-12-03	8,653	—	$0	77,872	SEC↗
Quane Alessandrea C.	EVP, Chief Insurance Officer	M Exercise deriv	2024-12-01	2024-12-03	34,379	—	$0	309,417	SEC↗
Quane Alessandrea C.	EVP, Chief Insurance Officer	M Exercise deriv	2024-12-01	2024-12-03	7,015	—	$0	21,048	SEC↗
Bopitiya Ranmali	EVP & Chief Legal Officer	M Exercise deriv	2024-12-01	2024-12-03	4,867	—	$0	43,803	SEC↗
Bopitiya Ranmali	EVP & Chief Legal Officer	M Exercise deriv	2024-12-01	2024-12-03	16,447	—	$0	148,027	SEC↗
Bopitiya Ranmali	EVP & Chief Legal Officer	M Exercise deriv	2024-12-01	2024-12-03	20,424	—	$0	102,125	SEC↗
Schlosser Mario	President of Technology & CT	M Exercise deriv	2024-12-01	2024-12-03	14,412	—	$0	129,705	SEC↗
Wolin Steven	Chief Operating Officer	M Exercise deriv	2024-12-01	2024-12-03	1,460	—	$0	13,141	SEC↗
Wolin Steven	Chief Operating Officer	M Exercise deriv	2024-12-01	2024-12-03	2,920	—	$0	26,282	SEC↗
Wolin Steven	Chief Operating Officer	M Exercise deriv	2024-12-01	2024-12-03	24,671	—	$0	123,356	SEC↗
Wolin Steven	Chief Operating Officer	M Exercise deriv	2024-12-01	2024-12-03	1,897	—	$0	1,897	SEC↗
Wolin Steven	Chief Operating Officer	M Exercise deriv	2024-12-01	2024-12-03	1,483	—	$0	1,483	SEC↗
Wolin Steven	Chief Operating Officer	M Exercise deriv	2024-12-01	2024-12-03	6,033	—	$0	6,034	SEC↗
Baltrus Victoria	Chief Accounting Officer	M Exercise	2024-12-01	2024-12-03	888	—	$0	154,114	SEC↗
Baltrus Victoria	Chief Accounting Officer	M Exercise	2024-12-01	2024-12-03	7,500	—	$0	153,226	SEC↗
Baltrus Victoria	Chief Accounting Officer	M Exercise	2024-12-01	2024-12-03	4,810	—	$0	141,606	SEC↗
Baltrus Victoria	Chief Accounting Officer	M Exercise	2024-12-01	2024-12-03	4,120	—	$0	145,726	SEC↗
Blackley Richard Scott	Chief Financial Officer	M Exercise	2024-12-01	2024-12-03	7,015	—	$0	860,890	SEC↗
Blackley Richard Scott	Chief Financial Officer	M Exercise	2024-12-01	2024-12-03	37,577	—	$0	898,467	SEC↗
Blackley Richard Scott	Chief Financial Officer	M Exercise	2024-12-01	2024-12-03	8,653	—	$0	907,120	SEC↗
Quane Alessandrea C.	EVP, Chief Insurance Officer	M Exercise	2024-12-01	2024-12-03	8,653	—	$0	442,654	SEC↗
Quane Alessandrea C.	EVP, Chief Insurance Officer	M Exercise	2024-12-01	2024-12-03	34,379	—	$0	434,001	SEC↗
Quane Alessandrea C.	EVP, Chief Insurance Officer	M Exercise	2024-12-01	2024-12-03	7,015	—	$0	399,622	SEC↗
Bopitiya Ranmali	EVP & Chief Legal Officer	M Exercise	2024-12-01	2024-12-03	16,447	—	$0	255,778	SEC↗
Bopitiya Ranmali	EVP & Chief Legal Officer	M Exercise	2024-12-01	2024-12-03	20,424	—	$0	239,331	SEC↗
Bopitiya Ranmali	EVP & Chief Legal Officer	M Exercise	2024-12-01	2024-12-03	4,867	—	$0	260,645	SEC↗
Schlosser Mario	President of Technology & CT	M Exercise	2024-12-01	2024-12-03	14,412	—	$0	88,478	SEC↗