MetaCap

Oscar Health Insider Trades

NYSE: OSCRHealth CareMedical SpecialitiesUSD

33.37+0.27 (+0.82%)

At close: Oct 9, 4:00 PM ET · Delayed 15 min

Last 12 months

Purchases
1 · $11.92M
Sales
49 · $136.88M
Shares bought / sold
1.00M / 4.75M
Net activity
Net selling $125.0 million

Oscar Health insider activity

Over the last 12 months, Oscar Health insiders reported 88 transactions on SEC Form 4: 1 open-market purchase and 49 sales. Insiders bought $11.9 million and sold $136.9 million worth of stock, for net insider selling of $125.0 million. The largest seller was Bertolini Mark T, with $70.7 million in reported sales.

The most recent filing shows WITTMAN VANESSA AMES (Director) selling 25,000 shares at $32.24 on Sep 18, 2026. Insider sales are common for compensation, tax and diversification reasons, while open-market purchases are rarer; tracking both helps put OSCR's ownership changes in context.

Summary generated from market data by MetaCap's automated system. Methodology

OSCR insider transactions

Oscar Health insider transactions
DateInsiderTypeSharesValueFiling
Sep 18, 2026Thrive 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.Directorother164,218—Form 4
Sep 18, 2026Thrive 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.Directorother4,855,810—Form 4
Sep 18, 2026Thrive 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.Directorother1,323,589—Form 4
Sep 18, 2026Thrive 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.Directorother164,218—Form 4
Sep 18, 2026Thrive 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.Directorother4,855,810—Form 4
Sep 18, 2026Thrive 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.Directorother1,323,589—Form 4
Sep 18, 2026Thrive 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.Directorother75,520—Form 4
Sep 18, 2026Thrive 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.Directorother6,268,097—Form 4
Sep 18, 2026Kushner JoshuaCo-Founder and Vice Chairmanother164,218—Form 4
Sep 18, 2026Kushner JoshuaCo-Founder and Vice Chairmanother4,855,810—Form 4
Sep 18, 2026Kushner JoshuaCo-Founder and Vice Chairmanother1,323,589—Form 4
Sep 18, 2026Kushner JoshuaCo-Founder and Vice Chairmanother164,218—Form 4
Sep 18, 2026Kushner JoshuaCo-Founder and Vice Chairmanother4,855,810—Form 4
Sep 18, 2026Kushner JoshuaCo-Founder and Vice Chairmanother1,323,589—Form 4
Sep 18, 2026Kushner JoshuaCo-Founder and Vice Chairmanother75,520—Form 4
Sep 18, 2026Kushner JoshuaCo-Founder and Vice Chairmanother6,268,097—Form 4
Sep 18, 2026WITTMAN VANESSA AMESDirectorSale25,000$806.00KForm 4
Sep 3, 2026Schlosser MarioDirectorSale31,422$988.22KForm 4
Sep 3, 2026McAnaney AdamChief Legal OfficerSale9,092$285.94KForm 4
Sep 3, 2026Baltrus VictoriaChief Accounting OfficerSale958$30.13KForm 4
Sep 3, 2026Liang JanetPresident, Oscar InsuranceSale10,360$325.82KForm 4
Sep 3, 2026Blackley Richard ScottChief Financial OfficerSale28,869$907.93KForm 4
Aug 28, 2026Schlosser MarioDirectorSale150,000$4.62MForm 4
Aug 28, 2026Schlosser MarioDirectorConversion150,000—Form 4
Aug 27, 2026Schlosser MarioDirectorSale600,000$18.20MForm 4
Aug 27, 2026Schlosser MarioDirectorConversion600,000—Form 4
Aug 18, 2026Blackley Richard ScottChief Financial OfficerSale18,750$595.13KForm 4
Jul 1, 2026Schlosser MarioDirectorSale30,228$956.72KForm 4
Jul 1, 2026Schlosser MarioDirectorSale13,672$421.10KForm 4
Jul 1, 2026Schlosser MarioDirectorSale3,600$106.20KForm 4
Jul 1, 2026Schlosser MarioDirectorConversion47,500—Form 4
Jun 30, 2026Bertolini Mark TChief Executive OfficerSale135,590$3.93MForm 4
Jun 30, 2026Bertolini Mark TChief Executive OfficerSale488,654$13.85MForm 4
Jun 29, 2026Bertolini Mark TChief Executive OfficerSale58,926$1.77MForm 4
Jun 29, 2026Bertolini Mark TChief Executive OfficerSale555,826$16.21MForm 4
Jun 26, 2026Bertolini Mark TChief Executive OfficerSale149,795$4.46MForm 4
Jun 26, 2026Bertolini Mark TChief Executive OfficerSale441,373$12.85MForm 4
Jun 25, 2026Bertolini Mark TChief Executive OfficerSale17,200$500.18KForm 4
Jun 25, 2026Bertolini Mark TChief Executive OfficerSale597,942$17.10MForm 4
Jun 23, 2026Schlosser MarioDirectorSale97$2.92KForm 4
Jun 23, 2026Schlosser MarioDirectorSale31,912$943.96KForm 4
Jun 23, 2026Schlosser MarioDirectorSale15,491$448.46KForm 4
Jun 23, 2026Schlosser MarioDirectorConversion47,500—Form 4
Jun 23, 2026Schlosser MarioDirectorSale102$3.07KForm 4
Jun 23, 2026Schlosser MarioDirectorSale33,592$993.65KForm 4
Jun 23, 2026Schlosser MarioDirectorSale16,306$472.06KForm 4
Jun 23, 2026Schlosser MarioDirectorConversion50,000—Form 4
Jun 23, 2026Schlosser MarioDirectorSale102$3.07KForm 4
Jun 23, 2026Schlosser MarioDirectorSale33,591$993.62KForm 4
Jun 23, 2026Schlosser MarioDirectorSale16,307$472.09KForm 4
Jun 23, 2026Schlosser MarioDirectorConversion50,000—Form 4
Jun 23, 2026Schlosser MarioDirectorSale1,799$54.13KForm 4
Jun 23, 2026Schlosser MarioDirectorSale591,213$17.49MForm 4
Jun 23, 2026Schlosser MarioDirectorSale286,988$8.31MForm 4
Jun 23, 2026Schlosser MarioDirectorConversion880,000—Form 4
Jun 4, 2026Gassen WilliamDirectorAward8,475—Form 4
Jun 4, 2026WITTMAN VANESSA AMESDirectorAward8,475—Form 4
Jun 4, 2026Lang Laura WDirectorAward8,475—Form 4
Jun 4, 2026Sankaran SidDirectorAward8,475—Form 4
Jun 4, 2026Plouffe DavidDirectorAward8,475—Form 4
Jun 2, 2026Blackley Richard ScottChief Financial OfficerSale8,977$201.53KForm 4
Jun 2, 2026Blackley Richard ScottChief Financial OfficerSale22,706$493.63KForm 4
Jun 2, 2026Liang JanetPresident, Oscar InsuranceSale3,535$79.36KForm 4
Jun 2, 2026Liang JanetPresident, Oscar InsuranceSale8,940$194.36KForm 4
Jun 2, 2026Schlosser MarioDirectorSale9,668$217.05KForm 4
Jun 2, 2026Schlosser MarioDirectorSale24,452$531.59KForm 4
Jun 2, 2026McAnaney AdamChief Legal OfficerSale2,794$62.73KForm 4
Jun 2, 2026McAnaney AdamChief Legal OfficerSale7,065$153.59KForm 4
Jun 2, 2026Baltrus VictoriaChief Accounting OfficerSale432$9.70KForm 4
Jun 2, 2026Baltrus VictoriaChief Accounting OfficerSale1,091$23.72KForm 4
May 18, 2026Blackley Richard ScottChief Financial OfficerSale110,000$2.75MForm 4
May 14, 2026Blackley Richard ScottChief Financial OfficerSale8,741$207.95KForm 4
May 14, 2026Blackley Richard ScottChief Financial OfficerSale91,259$2.11MForm 4
Apr 6, 2026Bertolini Mark TChief Executive OfficerBuy1,000,000$11.92MForm 4
Apr 6, 2026Bertolini Mark TChief Executive OfficerTax withholding1,000,001$11.92MForm 4
Apr 3, 2026Bertolini Mark TChief Executive OfficerOption exercise5,733,334—Form 4
Mar 12, 2026Blackley Richard ScottChief Financial OfficerGift75,000—Form 4
Mar 12, 2026Blackley Richard ScottChief Financial OfficerGift75,000—Form 4
Mar 12, 2026Blackley Richard ScottChief Financial OfficerGift75,000—Form 4
Mar 2, 2026Schlosser MarioPresident of Technology & CTOSale24,335$325.85KForm 4
Mar 2, 2026Schlosser MarioPresident of Technology & CTOAward189,141—Form 4
Mar 2, 2026McAnaney AdamChief Legal OfficerSale18,710$250.53KForm 4
Mar 2, 2026McAnaney AdamChief Legal OfficerAward67,424—Form 4
Mar 2, 2026Bertolini Mark TChief Executive OfficerAward1,596,877—Form 4
Mar 2, 2026Liang JanetPresident, Oscar InsuranceSale7,453$99.80KForm 4
Mar 2, 2026Liang JanetPresident, Oscar InsuranceAward106,458—Form 4
Mar 2, 2026Baltrus VictoriaChief Accounting OfficerSale4,638$62.10KForm 4
Mar 2, 2026Baltrus VictoriaChief Accounting OfficerAward17,300—Form 4

Transaction codes follow SEC Form 4: P = open-market purchase, S = open-market sale, A = grant or award, M = option exercise, F = shares withheld for taxes. About Form 4

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