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
2026-07-01
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
2026-03-02
Sale
2026-03-04
4:19 pm
Oscar Health Inc.OSCRBaltrus Victoria
Chief Accounting Officer
4,638$13.39$62,103216,112
(Direct)
View
2026-03-02
Sale
2026-03-04
4:18 pm
Oscar Health Inc.OSCRMcAnaney Adam
Chief Legal Officer
18,710$13.39$250,527227,955
(Direct)
View
2026-03-02
Sale
2026-03-04
4:17 pm
Oscar Health Inc.OSCRSchlosser Mario
President of Technology & CTO
24,335$13.39$325,846514,986
(Direct)
View
2026-03-02
Sale
2026-03-04
4:17 pm
Oscar Health Inc.OSCRBlackley Richard Scott
Chief Financial Officer
19,221$13.39$257,3691,466,660
(Direct)
View
2026-01-08
Sale
2026-01-12
4:18 pm
Oscar Health Inc.OSCRSchlosser Mario
President of Technology & CTO
23,038$17.65$406,6213,082,472
(Indirect
Direct)
View
2026-01-06
Sale
2026-01-08
4:17 pm
Oscar Health Inc.OSCRSchlosser Mario
President of Technology & CTO
76,962$17.01$1,309,1243,105,510
(Indirect
Direct)
View
2026-01-02
Sale
2026-01-06
4:18 pm
Oscar Health Inc.OSCRSchlosser Mario
President of Technology & CTO
234,861$15.28$3,587,7084,801,658
(Indirect
Direct)
View
2025-12-24
Sale
2025-12-30
4:16 pm
Oscar Health Inc.OSCRSchlosser Mario
President of Technology & CTO
38,835$15$582,525438,348
(Direct)
View
2025-12-02
Sale
2025-12-04
4:17 pm
Oscar Health Inc.OSCRMcAnaney Adam
Chief Legal Officer
1,852$16.59$30,725179,241
(Direct)
View
2025-12-02
Sale
2025-12-04
4:17 pm
Oscar Health Inc.OSCRSchlosser Mario
President of Technology & CTO
23,965$16.59$397,579477,183
(Direct)
View

Stock options: Exercise, Award, Grant, Conversion
Transaction
Date
Reported
DateTime
Exercisable
Expiration
CompanySymnbolInsider
Relationship
Shares
Traded
Conversion
Price
Shares
Owned
Filing
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
N/A
Oscar Health Inc.OSCRSchlosser Mario
Director
660,000$9.758,677,951
(Direct)
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
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
2026-03-02
Option Award
2026-03-04
4:19 pm
N/A
N/A
Oscar Health Inc.OSCRBaltrus Victoria
Chief Accounting Officer
17,300$0216,112
(Direct)
View
2026-03-02
Option Award
2026-03-04
4:18 pm
N/A
N/A
Oscar Health Inc.OSCRMcAnaney Adam
Chief Legal Officer
67,424$0227,955
(Direct)
View
2026-03-02
Option Award
2026-03-04
4:17 pm
N/A
N/A
Oscar Health Inc.OSCRSchlosser Mario
President of Technology & CTO
189,141$0514,986
(Direct)
View
2026-03-02
Option Award
2026-03-04
4:17 pm
N/A
N/A
Oscar Health Inc.OSCRBlackley Richard Scott
Chief Financial Officer
134,847$01,466,660
(Direct)
View
2026-01-08
Option Award
2026-01-12
4:21 pm
N/A
N/A
Oscar Health Inc.OSCRBOYD JEFFERY H
Director
3,106$16.966,248
(Direct)
View
2026-01-08
Option Award
2026-01-12
4:21 pm
N/A
N/A
Oscar Health Inc.OSCRGassen William
Director
1,220$16.94,969
(Direct)
View
2026-01-08
Option Award
2026-01-12
4:18 pm
N/A
N/A
Oscar Health Inc.OSCRPlouffe David
Director
1,257$16.95,393
(Direct)
View
2026-01-08
Conversion
2026-01-12
4:18 pm
N/A
N/A
Oscar Health Inc.OSCRSchlosser Mario
President of Technology & CTO
23,038$03,082,472
(Direct)
View
2026-01-06
Conversion
2026-01-08
4:17 pm
N/A
N/A
Oscar Health Inc.OSCRSchlosser Mario
President of Technology & CTO
76,962$03,105,510
(Direct)
View
2026-01-02
Conversion
2026-01-06
4:18 pm
N/A
N/A
Oscar Health Inc.OSCRSchlosser Mario
President of Technology & CTO
146,693$04,801,658
(Direct)
View
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