Oscar Health Inc. (OSCR) - Insider Trading & Ownership

Real time insider trading transaction history:

  • Insiders are prohibited from making short-swing profits by trading their shares within 6 months of the registration or acquiring the shares.
  • Shares are not adjusted for stock split.
"Insiders might sell their shares for any number of reasons, but they buy them for only one: they think the price will rise"
- Peter Lynch
What is insider trading>>
Time period
Insider Trading Transactions for Oscar Health Inc.
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Common stock purchase or sale:
Transaction
Date
Reported
DateTime
CompanySymbolInsider
Relationship
Shares
Traded
Average
Price
Total
Amount
Shares
Owned
Filing
2026-09-18
Sale
2026-09-22
4:20 pm
Oscar Health Inc.OSCRWITTMAN VANESSA AMES
Director
25,000$32.24$806,000112,121
(Direct)
View
2026-09-03
Sale
2026-09-08
4:22 pm
Oscar Health Inc.OSCRLiang Janet
President, Oscar Insurance
10,360$31.45$325,822248,697
(Direct)
View
2026-09-03
Sale
2026-09-08
4:16 pm
Oscar Health Inc.OSCRBaltrus Victoria
Chief Accounting Officer
958$31.45$30,129213,631
(Direct)
View
2026-09-03
Sale
2026-09-08
4:16 pm
Oscar Health Inc.OSCRBlackley Richard Scott
Chief Financial Officer
28,869$31.45$907,9301,102,358
(Indirect
Direct)
View
2026-09-03
Sale
2026-09-08
4:16 pm
Oscar Health Inc.OSCRMcAnaney Adam
Chief Legal Officer
9,092$31.45$285,943209,004
(Direct)
View
2026-09-03
Sale
2026-09-08
4:16 pm
Oscar Health Inc.OSCRSchlosser Mario
Director
31,422$31.45$988,222449,444
(Direct)
View
2026-08-27
Sale
2026-08-31
4:16 pm
Oscar Health Inc.OSCRSchlosser Mario
Director
750,000$30.43$22,822,50013,315,037
(Indirect
Direct)
View
2026-08-18
Sale
2026-08-20
4:16 pm
Oscar Health Inc.OSCRBlackley Richard Scott
Chief Financial Officer
18,750$31.74$595,1251,131,227
(Indirect
Direct)
View
2026-07-01
Sale
2026-07-06
4:11 pm
Oscar Health Inc.OSCRSchlosser Mario
Director
47,500$31.24$1,484,0142,798,158
(Indirect
Direct)
View
2026-06-29
Sale
2026-07-01
4:16 pm
Oscar Health Inc.OSCRBertolini Mark T
Chief Executive Officer
1,238,996$28.87$35,767,3227,751,570
(Direct)
View
2026-06-25
Sale
2026-06-29
4:17 pm
Oscar Health Inc.OSCRBertolini Mark T
Chief Executive Officer
1,206,310$28.94$34,912,0788,990,566
(Direct)
View
2026-06-23
Sale
2026-06-25
4:17 pm
Oscar Health Inc.OSCRSchlosser Mario
Director
1,027,500$29.38$30,183,4138,677,951
(Indirect
Direct)
View
2026-06-02
Sale
2026-06-04
4:17 pm
Oscar Health Inc.OSCRBaltrus Victoria
Chief Accounting Officer
1,523$21.94$33,417214,589
(Direct)
View
2026-06-02
Sale
2026-06-04
4:16 pm
Oscar Health Inc.OSCRSchlosser Mario
Director
34,120$21.94$748,633480,866
(Direct)
View
2026-06-02
Sale
2026-06-04
4:16 pm
Oscar Health Inc.OSCRMcAnaney Adam
Chief Legal Officer
9,859$21.94$216,318218,096
(Direct)
View
2026-06-02
Sale
2026-06-04
4:16 pm
Oscar Health Inc.OSCRLiang Janet
President, Oscar Insurance
12,475$21.94$273,716259,057
(Direct)
View
2026-06-02
Sale
2026-06-04
4:15 pm
Oscar Health Inc.OSCRBlackley Richard Scott
Chief Financial Officer
31,683$21.94$695,1621,149,977
(Indirect
Direct)
View
2026-05-18
Sale
2026-05-20
4:17 pm
Oscar Health Inc.OSCRBlackley Richard Scott
Chief Financial Officer
110,000$25.03$2,753,3001,181,660
(Indirect
Direct)
View
2026-05-14
Sale
2026-05-18
4:15 pm
Oscar Health Inc.OSCRBlackley Richard Scott
Chief Financial Officer
100,000$23.16$2,316,0311,291,660
(Indirect
Direct)
View
2026-04-06
Purchase
2026-04-07
4:16 pm
Oscar Health Inc.OSCRBertolini Mark T
Chief Executive Officer
1,000,000$11.92$11,920,00010,196,876
(Direct)
View
2026-03-02
Sale
2026-03-04
4:23 pm
Oscar Health Inc.OSCRLiang Janet
President, Oscar Insurance
7,453$13.39$99,796271,532
(Direct)
View

Stock options: Exercise, Award, Grant, Conversion
Transaction
Date
Reported
DateTime
Exercisable
Expiration
CompanySymnbolInsider
Relationship
Shares
Traded
Conversion
Price
Shares
Owned
Filing
2026-10-08
Option Award
2026-10-13
4:17 pm
N/A
N/A
Oscar Health Inc.OSCRPlouffe David
Director
641$33.18,176
(Direct)
View
2026-10-08
Option Award
2026-10-13
4:16 pm
N/A
N/A
Oscar Health Inc.OSCRSankaran Sid
Director
1,472$33.13,533
(Direct)
View
2026-10-08
Option Award
2026-10-13
4:16 pm
N/A
N/A
Oscar Health Inc.OSCRGassen William
Director
698$33.17,769
(Direct)
View
2026-09-18
Other
2026-09-18
8:27 pm
N/A
N/A
Oscar Health Inc.OSCRKushner Joshua
Co-Founder and Vice Chairman
Director
10% Owner
12,687,234$051,889,915
(Indirect)
View
2026-09-18
Other
2026-09-18
8:21 pm
N/A
N/A
Oscar Health Inc.OSCRThrive Partners II GP LLC
Thrive Capital Partners II L.P.
Thrive Partners III GP LLC
Thrive Capital Partners III L.P.
Claremount TW L.P.
Thrive Partners VII Growth GP LLC
Thrive Capital Partners VII Growth L.P.
Thrive Partners VII GP LLC
Claremount VII Associates L.P.
Director
10% Owner
12,687,234$051,889,915
(Indirect)
View
2026-08-27
Exercise
2026-08-31
4:16 pm
N/A
2029-12-16
Oscar Health Inc.OSCRSchlosser Mario
Director
750,000$013,315,037
(Direct)
View
2026-08-27
Exercise
2026-08-31
4:16 pm
N/A
N/A
Oscar Health Inc.OSCRSchlosser Mario
Director
750,000$9.7513,315,037
(Direct)
View
2026-08-27
Conversion
2026-08-31
4:16 pm
N/A
N/A
Oscar Health Inc.OSCRSchlosser Mario
Director
750,000$013,315,037
(Direct)
View
2026-07-09
Option Award
2026-07-13
4:16 pm
N/A
N/A
Oscar Health Inc.OSCRGassen William
Director
684$31.27,071
(Direct)
View
2026-07-09
Option Award
2026-07-13
4:16 pm
N/A
N/A
Oscar Health Inc.OSCRSankaran Sid
Director
858$31.22,061
(Direct)
View
2026-07-09
Option Award
2026-07-13
4:14 pm
N/A
N/A
Oscar Health Inc.OSCRPlouffe David
Director
681$31.27,535
(Direct)
View
2026-07-01
Conversion
2026-07-06
4:11 pm
N/A
N/A
Oscar Health Inc.OSCRSchlosser Mario
Director
47,500$02,798,158
(Indirect)
View
2026-06-23
Exercise
2026-06-25
4:17 pm
N/A
2029-12-16
Oscar Health Inc.OSCRSchlosser Mario
Director
660,000$08,677,951
(Direct)
View
2026-06-23
Exercise
2026-06-25
4:17 pm
N/A
N/A
Oscar Health Inc.OSCRSchlosser Mario
Director
660,000$9.758,677,951
(Direct)
View
2026-06-23
Conversion
2026-06-25
4:17 pm
N/A
N/A
Oscar Health Inc.OSCRSchlosser Mario
Director
1,027,500$08,677,951
(Direct)
View
2026-06-04
Option Award
2026-06-08
4:18 pm
N/A
N/A
Oscar Health Inc.OSCRLang Laura W
Director
8,475$082,840
(Direct)
View
2026-06-04
Option Award
2026-06-08
4:18 pm
N/A
N/A
Oscar Health Inc.OSCRPlouffe David
Director
8,475$0137,121
(Direct)
View
2026-06-04
Option Award
2026-06-08
4:18 pm
N/A
N/A
Oscar Health Inc.OSCRSankaran Sid
Director
8,475$0818,295
(Direct)
View
2026-06-04
Option Award
2026-06-08
4:18 pm
N/A
N/A
Oscar Health Inc.OSCRGassen William
Director
8,475$082,840
(Direct)
View
2026-06-04
Option Award
2026-06-08
4:17 pm
N/A
N/A
Oscar Health Inc.OSCRWITTMAN VANESSA AMES
Director
8,475$0137,121
(Direct)
View
2026-04-09
Option Award
2026-04-13
4:16 pm
N/A
N/A
Oscar Health Inc.OSCRSankaran Sid
Director
1,203$14.541,203
(Direct)
View
2026-04-09
Option Award
2026-04-13
4:16 pm
N/A
N/A
Oscar Health Inc.OSCRGassen William
Director
1,418$14.546,387
(Direct)
View
2026-04-09
Option Award
2026-04-13
4:15 pm
N/A
N/A
Oscar Health Inc.OSCRBOYD JEFFERY H
Director
3,610$14.5469,858
(Direct)
View
2026-04-09
Option Award
2026-04-13
4:15 pm
N/A
N/A
Oscar Health Inc.OSCRPlouffe David
Director
1,461$14.546,854
(Direct)
View
2026-04-03
Exercise
2026-04-07
4:16 pm
N/A
N/A
Oscar Health Inc.OSCRBertolini Mark T
Chief Executive Officer
5,733,334$010,196,876
(Direct)
View
2026-04-06
Tax Withholding
2026-04-07
4:16 pm
N/A
N/A
Oscar Health Inc.OSCRBertolini Mark T
Chief Executive Officer
1,000,001$11.9210,196,876
(Direct)
View
2026-03-12
Gift
2026-03-16
4:24 pm
N/A
N/A
Oscar Health Inc.OSCRBlackley Richard Scott
Chief Financial Officer
75,000$01,391,660
(Direct)
View
2026-03-02
Option Award
2026-03-04
4:23 pm
N/A
N/A
Oscar Health Inc.OSCRLiang Janet
President, Oscar Insurance
106,458$0271,532
(Direct)
View
2026-03-02
Option Award
2026-03-04
4:22 pm
N/A
N/A
Oscar Health Inc.OSCRBertolini Mark T
Chief Executive Officer
1,596,877$04,463,543
(Direct)
View
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