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
2026-04-06
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
2025-12-02
Sale
2025-12-04
4:17 pm
Oscar Health Inc.OSCRLiang Janet
President, Oscar Insurance
7,338$16.59$121,737172,527
(Direct)
View
2025-12-02
Sale
2025-12-04
4:16 pm
Oscar Health Inc.OSCRBlackley Richard Scott
Chief Financial Officer
25,135$16.59$416,9901,351,034
(Direct)
View
2025-12-02
Sale
2025-12-04
4:16 pm
Oscar Health Inc.OSCRBaltrus Victoria
Chief Accounting Officer
4,149$16.59$68,832203,450
(Direct)
View
2025-11-11
Sale
2025-11-13
4:18 pm
Oscar Health Inc.OSCRSchlosser Mario
President of Technology & CTO
391,482$15.21$5,954,7648,977,843
(Indirect
Direct)
View
2025-09-22
Sale
2025-09-24
4:20 pm
Oscar Health Inc.OSCRSchlosser Mario
President of Technology & CTO
395,000$18.43$7,279,8505,781,918
(Indirect
Direct)
View

Stock options: Exercise, Award, Grant, Conversion
Transaction
Date
Reported
DateTime
Exercisable
Expiration
CompanySymnbolInsider
Relationship
Shares
Traded
Conversion
Price
Shares
Owned
Filing
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
2025-11-11
Exercise
2025-11-13
4:18 pm
N/A
2025-12-07
Oscar Health Inc.OSCRSchlosser Mario
President of Technology & CTO
555,165$08,977,843
(Direct)
View
2025-11-11
Exercise
2025-11-13
4:18 pm
N/A
N/A
Oscar Health Inc.OSCRSchlosser Mario
President of Technology & CTO
555,165$6.368,977,843
(Direct)
View
2025-11-11
Conversion
2025-11-13
4:18 pm
N/A
N/A
Oscar Health Inc.OSCRSchlosser Mario
President of Technology & CTO
391,482$08,977,843
(Direct)
View
2025-10-09
Option Award
2025-10-14
4:36 pm
N/A
N/A
Oscar Health Inc.OSCRGassen William
Director
1,004$20.543,749
(Direct)
View
2025-10-09
Option Award
2025-10-14
4:36 pm
N/A
N/A
Oscar Health Inc.OSCRPlouffe David
Director
1,034$20.544,136
(Direct)
View
2025-10-09
Option Award
2025-10-14
4:35 pm
N/A
N/A
Oscar Health Inc.OSCRBOYD JEFFERY H
Director
2,555$20.5463,142
(Direct)
View
2025-09-22
Exercise
2025-09-24
4:20 pm
N/A
2025-12-07
Oscar Health Inc.OSCRSchlosser Mario
President of Technology & CTO
555,165$05,781,918
(Direct)
View
2025-09-22
Exercise
2025-09-24
4:20 pm
N/A
N/A
Oscar Health Inc.OSCRSchlosser Mario
President of Technology & CTO
555,165$6.365,781,918
(Direct)
View
2025-09-22
Conversion
2025-09-24
4:20 pm
N/A
N/A
Oscar Health Inc.OSCRSchlosser Mario
President of Technology & CTO
395,000$05,781,918
(Direct)
View
2025-09-02
Tax Withholding
2025-09-04
4:17 pm
N/A
N/A
Oscar Health Inc.OSCRBaltrus Victoria
Chief Accounting Officer
6,266$16.66207,599
(Direct)
View
2025-09-02
Tax Withholding
2025-09-04
4:17 pm
N/A
N/A
Oscar Health Inc.OSCRBlackley Richard Scott
Chief Financial Officer
28,166$16.661,376,169
(Direct)
View
2025-09-02
Tax Withholding
2025-09-04
4:16 pm
N/A
N/A
Oscar Health Inc.OSCRLiang Janet
President, Oscar Insurance
7,303$16.66179,865
(Direct)
View
2025-09-02
Tax Withholding
2025-09-04
4:16 pm
N/A
N/A
Oscar Health Inc.OSCRMcAnaney Adam
Chief Legal Officer
1,845$16.66181,093
(Direct)
View
2025-09-02
Tax Withholding
2025-09-04
4:16 pm
N/A
N/A
Oscar Health Inc.OSCRSchlosser Mario
President of Technology & CTO
23,879$16.66501,148
(Direct)
View
2025-07-10
Option Award
2025-07-14
4:16 pm
N/A
N/A
Oscar Health Inc.OSCRPlouffe David
Director
1,368$15.533,102
(Direct)
View
2025-07-10
Option Award
2025-07-14
4:16 pm
N/A
N/A
Oscar Health Inc.OSCRGassen William
Director
1,215$15.532,745
(Direct)
View
2025-07-10
Option Award
2025-07-14
4:16 pm
N/A
N/A
Oscar Health Inc.OSCRBOYD JEFFERY H
Director
3,380$15.5360,587
(Direct)
View
2025-06-04
Option Award
2025-06-06
4:23 pm
N/A
N/A
Oscar Health Inc.OSCRBOYD JEFFERY H
Director
14,134$0705,673
(Direct)
View
2025-06-04
Option Award
2025-06-06
4:23 pm
N/A
N/A
Oscar Health Inc.OSCRLang Laura W
Director
14,134$074,365
(Direct)
View
2025-06-04
Option Award
2025-06-06
4:23 pm
N/A
N/A
Oscar Health Inc.OSCRPlouffe David
Director
14,134$0128,646
(Direct)
View
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