United States Insurance

Oscar Health Inc (OSCR)

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Oscar Health Inc. experienced significant insider trading activity over the past ninety days, totaling 239.65 million dollars in sales. Key executives, including CEO Mark Bertolini, executed numerous planned divestments following a strong earnings report. These transactions reflect substantial liquidity events by leadership despite the stock maintaining a positive performance trend recently.
Ticker: OSCR Exchange: NYS
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• Purchase • Sale • Planned purchase • Planned sale Net purchase Net sale Buy signal Sell signal Earnings
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Trades
Proposed sale 10 Aug 2026
Value US$2,738,809.02 | Price 449.40 | Shares 41,686
Abbreviations B: Buy, S: Sell, PP: Planned purchase, PlS: Planned sale, PrS: Proposed sale, O: Option / Other
Notification date Transaction date B/S Transaction type Insider and/or position Nb. shares
Price
Value 		Number of shares Price Value Details
2026-08-10 2026-08-10 PrS Proposed sale
BOYD JEFFERY H

Former Director

Non-Executive Director
41,686
449.40
US$2,738,809 		41,686 449.40 US$2,738,809
2026-08-10 2026-08-10 PrS Proposed sale
JEFFERY H. BOYD

Former Affiliate
66,387
384.60
US$1,950,537 		66,387 384.60 US$1,950,537
2026-07-06 2026-07-01 PlS Planned sale
1.8
Schlosser Mario
Non-Executive Director
51,029 +46.2%
313.04
US$724,947 		51,029 +46.2% 313.04 US$724,947
2026-07-06 2026-07-01 PlS Planned sale
1.8
Schlosser Mario
Non-Executive Director
13,672 -31.1%
30.80
US$421,098 		13,672 -31.1% 30.80 US$421,098
2026-07-06 2026-07-01 PlS Planned sale
1.8
Schlosser Mario
Non-Executive Director
3,600 -7.6%
29.50
US$106,200 		3,600 -7.6% 29.50 US$106,200
2026-07-01 2026-06-30 PlS Planned sale
3.4
Bertolini Mark T

Chief Executive Officer

Executive Director
135,590 -1.7%
28.97
US$3,928,042 		135,590 -1.7% 28.97 US$3,928,042
2026-07-01 2026-06-30 PlS Planned sale
3.4
Bertolini Mark T

Chief Executive Officer

Executive Director
488,654 -5.8%
28.35
US$13,853,341 		488,654 -5.8% 28.35 US$13,853,341
2026-07-01 2026-06-29 PlS Planned sale
3.4
Bertolini Mark T

Chief Executive Officer

Executive Director
58,926 -0.7%
30.08
US$1,772,494 		58,926 -0.7% 30.08 US$1,772,494
2026-07-01 2026-06-29 PlS Planned sale
3.4
Bertolini Mark T

Chief Executive Officer

Executive Director
555,826 -6.2%
29.17
US$16,213,444 		555,826 -6.2% 29.17 US$16,213,444
2026-06-29 2026-06-26 PlS Planned sale
3.4
Bertolini Mark T

Chief Executive Officer

Executive Director
149,795 -1.6%
29.79
US$4,462,393 		149,795 -1.6% 29.79 US$4,462,393
2026-06-29 2026-06-26 PlS Planned sale
3.4
Bertolini Mark T

Chief Executive Officer

Executive Director
441,373 -4.6%
29.11
US$12,848,368 		441,373 -4.6% 29.11 US$12,848,368
2026-06-29 2026-06-25 PlS Planned sale
3.4
Bertolini Mark T

Chief Executive Officer

Executive Director
17,200 -0.2%
29.08
US$500,176 		17,200 -0.2% 29.08 US$500,176
2026-06-29 2026-06-25 PlS Planned sale
3.4
Bertolini Mark T

Chief Executive Officer

Executive Director
597,942 -5.9%
28.60
US$17,101,141 		597,942 -5.9% 28.60 US$17,101,141
2026-06-25 2026-06-25 PrS Proposed sale
3.4
Mark Bertolini

Director; CEO

Non-Executive Director
2,776,937
29.93
US$83,113,724 		2,776,937 29.93 US$83,113,724
2026-06-25 2026-06-23 PlS Planned sale
1.8
Schlosser Mario
Non-Executive Director
97 -100.0%
30.09
US$2,919 		97 -100.0% 30.09 US$2,919
2026-06-25 2026-06-23 PlS Planned sale
1.8
Schlosser Mario
Non-Executive Director
31,912 -99.7%
29.58
US$943,957 		31,912 -99.7% 29.58 US$943,957
2026-06-25 2026-06-23 PlS Planned sale
1.8
Schlosser Mario
Non-Executive Director
15,491 -32.6%
28.95
US$448,464 		15,491 -32.6% 28.95 US$448,464
2026-06-25 2026-06-23 PlS Planned sale
1.8
Schlosser Mario
Non-Executive Director
102 -100.0%
30.09
US$3,069 		102 -100.0% 30.09 US$3,069
2026-06-25 2026-06-23 PlS Planned sale
1.8
Schlosser Mario
Non-Executive Director
33,592 -99.7%
29.58
US$993,651 		33,592 -99.7% 29.58 US$993,651
2026-06-25 2026-06-23 PlS Planned sale
1.8
Schlosser Mario
Non-Executive Director
16,306 -32.6%
28.95
US$472,059 		16,306 -32.6% 28.95 US$472,059
2026-06-25 2026-06-23 PlS Planned sale
1.8
Schlosser Mario
Non-Executive Director
102 -100.0%
30.09
US$3,069 		102 -100.0% 30.09 US$3,069
2026-06-25 2026-06-23 PlS Planned sale
1.8
Schlosser Mario
Non-Executive Director
33,591 -99.7%
29.58
US$993,622 		33,591 -99.7% 29.58 US$993,622
2026-06-25 2026-06-23 PlS Planned sale
1.8
Schlosser Mario
Non-Executive Director
16,307 -32.6%
28.95
US$472,088 		16,307 -32.6% 28.95 US$472,088
2026-06-25 2026-06-23 PlS Planned sale
1.8
Schlosser Mario
Non-Executive Director
1,799 -0.4%
30.09
US$54,132 		1,799 -0.4% 30.09 US$54,132
2026-06-25 2026-06-23 PlS Planned sale
1.8
Schlosser Mario
Non-Executive Director
591,213 -55.1%
29.58
US$17,488,081 		591,213 -55.1% 29.58 US$17,488,081
2026-06-25 2026-06-23 PlS Planned sale
1.8
Schlosser Mario
Non-Executive Director
286,988 -21.1%
28.95
US$8,308,303 		286,988 -21.1% 28.95 US$8,308,303
2026-06-23 2026-06-23 PrS Proposed sale
1.8
Noah Pizzo-Schlosser Dynasty Trust

Director

Non-Executive Director
50,000
28.54
US$1,427,000 		50,000 28.54 US$1,427,000
2026-06-23 2026-06-23 PrS Proposed sale
1.8
Pizzo-Schlosser Family Dynasty Trust

Director

Non-Executive Director
95,000
28.54
US$2,711,300 		95,000 28.54 US$2,711,300
2026-06-23 2026-06-23 PrS Proposed sale
1.8
Siena Pizzo-Schlosser Dynasty Trust

Director

Non-Executive Director
50,000
28.54
US$1,427,000 		50,000 28.54 US$1,427,000
2026-06-23 2026-06-23 PrS Proposed sale
1.8
MARIO SCHLOSSER

Director

Non-Executive Director
880,000
28.54
US$25,115,200 		880,000 28.54 US$25,115,200
2026-06-04 2026-06-02 PlS Planned sale
2.2
Blackley Richard Scott

Chief Financial Officer

Officer
8,977 -0.8%
22.45
US$201,534 		8,977 -0.8% 22.45 US$201,534
2026-06-04 2026-06-02 PlS Planned sale
2.2
Blackley Richard Scott

Chief Financial Officer

Officer
22,706 -2.1%
21.74
US$493,628 		22,706 -2.1% 21.74 US$493,628
2026-06-04 2026-06-02 PlS Planned sale
McAnaney Adam

Chief Legal Officer

Officer
2,794 -1.3%
22.45
US$62,725 		2,794 -1.3% 22.45 US$62,725
2026-06-04 2026-06-02 PlS Planned sale
McAnaney Adam

Chief Legal Officer

Officer
7,065 -3.1%
21.74
US$153,593 		7,065 -3.1% 21.74 US$153,593
2026-06-04 2026-06-02 PlS Planned sale
1.8
Schlosser Mario
Non-Executive Director
9,668 -2.0%
22.45
US$217,047 		9,668 -2.0% 22.45 US$217,047
2026-06-04 2026-06-02 PlS Planned sale
1.8
Schlosser Mario
Non-Executive Director
24,452 -4.7%
21.74
US$531,586 		24,452 -4.7% 21.74 US$531,586
2026-06-04 2026-06-02 PlS Planned sale
Liang Janet

President, Oscar Insurance

Officer
3,535 -1.3%
22.45
US$79,361 		3,535 -1.3% 22.45 US$79,361
2026-06-04 2026-06-02 PlS Planned sale
Liang Janet

President, Oscar Insurance

Officer
8,940 -3.3%
21.74
US$194,356 		8,940 -3.3% 21.74 US$194,356
2026-06-04 2026-06-02 PlS Planned sale
Baltrus Victoria

Chief Accounting Officer

Officer
432 -0.2%
22.45
US$9,698 		432 -0.2% 22.45 US$9,698
2026-06-04 2026-06-02 PlS Planned sale
Baltrus Victoria

Chief Accounting Officer

Officer
1,091 -0.5%
21.74
US$23,718 		1,091 -0.5% 21.74 US$23,718
2026-06-02 2026-06-02 PrS Proposed sale
1.8
Mario Schlosser

Director

Non-Executive Director
37,488
22.23
US$833,358 		37,488 22.23 US$833,358
2026-06-02 2026-06-02 PrS Proposed sale
Adam McAnaney

Chief Legal Officer

Officer
10,832
22.23
US$240,795 		10,832 22.23 US$240,795
2026-06-02 2026-06-02 PrS Proposed sale
2.2
Richard Scott Blackley

CFO
34,808
22.23
US$773,782 		34,808 22.23 US$773,782
2026-06-02 2026-06-02 PrS Proposed sale
Janet Liang

President, Oscar Insurance
13,706
22.23
US$304,684 		13,706 22.23 US$304,684
2026-05-20 2026-05-18 PlS Planned sale
2.2
Blackley Richard Scott

Chief Financial Officer

Officer
110,000 -9.0%
25.03
US$2,753,300 		110,000 -9.0% 25.03 US$2,753,300
2026-05-18 2026-05-18 PrS Proposed sale
2.2
RICHARD SCOTT BLACKLEY

Officer

Officer
110,000
23.32
US$2,565,200 		110,000 23.32 US$2,565,200
2026-05-18 2026-05-14 PlS Planned sale
2.2
Blackley Richard Scott

Chief Financial Officer

Officer
8,741 -0.7%
23.79
US$207,948 		8,741 -0.7% 23.79 US$207,948
2026-05-18 2026-05-14 PlS Planned sale
2.2
Blackley Richard Scott

Chief Financial Officer

Officer
8,741 -0.7%
23.79
US$207,948 		8,741 -0.7% 23.79 US$207,948
2026-05-18 2026-05-14 PlS Planned sale
2.2
Blackley Richard Scott

Chief Financial Officer

Officer
91,259 -6.9%
23.10
US$2,108,083 		91,259 -6.9% 23.10 US$2,108,083
2026-05-18 2026-05-14 PlS Planned sale
2.2
Blackley Richard Scott

Chief Financial Officer

Officer
91,259 -6.9%
23.10
US$2,108,083 		91,259 -6.9% 23.10 US$2,108,083
2026-05-14 2026-05-14 PrS Proposed sale
2.2
RICHARD SCOTT BLACKLEY

Officer

Officer
100,000
23.62
US$2,362,000 		100,000 23.62 US$2,362,000
2026-04-07 2026-04-06 B Purchase
3.4
Bertolini Mark T

Chief Executive Officer

Executive Director
1,000,000 +10.9%
11.92
US$11,920,000 		1,000,000 +10.9% 11.92 US$11,920,000
2026-03-04 2026-03-02 PlS Planned sale
Liang Janet

President, Oscar Insurance

Officer
7,453 -2.7%
13.39
US$99,796 		7,453 -2.7% 13.39 US$99,796
2026-03-04 2026-03-02 PlS Planned sale
Baltrus Victoria

Chief Accounting Officer

Officer
4,638 -2.1%
13.39
US$62,103 		4,638 -2.1% 13.39 US$62,103
2026-03-04 2026-03-02 PlS Planned sale
McAnaney Adam

Chief Legal Officer

Officer
18,710 -7.6%
13.39
US$250,527 		18,710 -7.6% 13.39 US$250,527
2026-03-04 2026-03-02 PlS Planned sale
1.8
Schlosser Mario

President of Technology & CTO

Executive Director
24,335 -4.5%
13.39
US$325,846 		24,335 -4.5% 13.39 US$325,846
2026-03-04 2026-03-02 PlS Planned sale
2.2
Blackley Richard Scott

Chief Financial Officer

Officer
19,221 -1.3%
13.39
US$257,369 		19,221 -1.3% 13.39 US$257,369
2026-03-02 2026-03-02 PrS Proposed sale
2.2
Blackley Richard Scott

Chief Financial Officer

Officer
19,638
13.66
US$268,255 		19,638 13.66 US$268,255
2026-03-02 2026-03-02 PrS Proposed sale
Adam McAnaney

Chief Legal Officer

Officer
15,530
13.66
US$212,140 		15,530 13.66 US$212,140
2026-03-02 2026-03-02 PrS Proposed sale
1.8
Schlosser Mario

Officer / Director

Executive Director
20,629
13.66
US$281,792 		20,629 13.66 US$281,792
2026-03-02 2026-03-02 PrS Proposed sale
Janet Liang

President, Oscar Insurance
6,468
13.66
US$88,353 		6,468 13.66 US$88,353
2026-01-12 2026-01-08 PlS Planned sale
1.8
Schlosser Mario

President of Technology & CTO

Executive Director
23,038 -6.2%
17.65
US$406,621 		23,038 -6.2% 17.65 US$406,621
2026-01-08 2026-01-06 PlS Planned sale
1.8
Schlosser Mario

President of Technology & CTO

Executive Director
76,962 -18.0%
17.01
US$1,309,124 		76,962 -18.0% 17.01 US$1,309,124
2026-01-06 2026-01-06 PrS Proposed sale
1.8
MARIO SCHLOSSER

Director; Officer

Executive Director
100,000
16.57
US$1,657,000 		100,000 16.57 US$1,657,000
2026-01-06 2026-01-05 PlS Planned sale
1.8
Schlosser Mario

President of Technology & CTO

Executive Director
96,928 -21.7%
15.64
US$1,515,954 		96,928 -21.7% 15.64 US$1,515,954
2026-01-06 2026-01-02 PlS Planned sale
1.8
Schlosser Mario

President of Technology & CTO

Executive Director
137,933 -27.7%
15.02
US$2,071,754 		137,933 -27.7% 15.02 US$2,071,754
2026-01-02 2026-01-02 PrS Proposed sale
1.8
MARIO SCHLOSSER

Director; Officer

Executive Director
216,396
14.37
US$3,109,611 		216,396 14.37 US$3,109,611
2025-12-30 2025-12-24 PlS Planned sale
1.8
Schlosser Mario

President of Technology & CTO

Executive Director
38,835 -8.1%
15.00
US$582,525 		38,835 -8.1% 15.00 US$582,525
2025-12-29 2025-12-24 PrS Proposed sale
1.8
MARIO SCHLOSSER

Director; Officer

Executive Director
57,300
14.84
US$850,332 		57,300 14.84 US$850,332
2025-12-04 2025-12-02 PlS Planned sale
Baltrus Victoria

Chief Accounting Officer

Officer
4,149 -2.0%
16.59
US$68,832 		4,149 -2.0% 16.59 US$68,832
2025-12-04 2025-12-02 PlS Planned sale
1.8
Schlosser Mario

President of Technology & CTO

Executive Director
23,965 -4.8%
16.59
US$397,579 		23,965 -4.8% 16.59 US$397,579
2025-12-04 2025-12-02 PlS Planned sale
McAnaney Adam

Chief Legal Officer

Officer
1,852 -1.0%
16.59
US$30,725 		1,852 -1.0% 16.59 US$30,725
2025-12-04 2025-12-02 PlS Planned sale
2.2
Blackley Richard Scott

Chief Financial Officer

Officer
25,135 -1.8%
16.59
US$416,990 		25,135 -1.8% 16.59 US$416,990
2025-12-04 2025-12-02 PlS Planned sale
Liang Janet

President, Oscar Insurance

Officer
7,338 -4.1%
16.59
US$121,737 		7,338 -4.1% 16.59 US$121,737
2025-12-02 2025-12-02 PrS Proposed sale
Janet Liang

President, Oscar Insurance
8,398
16.73
US$140,499 		8,398 16.73 US$140,499
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