greeksoup/ stock research
Stock research / United States / OSCR / Planned sales

Oscar Health, Inc. planned insider sales

In the last twelve months insiders at Oscar Health, Inc. filed 36 Form 144 notices of planned sales, 6.7 million shares worth $186.4 million at the time of filing, from 18 sellers. The latest, filed 18 September 2026: Wittman Vanessa Ames (officer), 25,000 shares worth $806,000, planned for around 18 September 2026 through Merrill Lynch.

FiledSellerRelationshipSharesValuePlanned saleSold, per Form 4BrokerHow acquiredFiling
18 September 2026Wittman Vanessa AmesOfficer25,000$806,00018 September 202625,000 shares from 18 September 2026Merrill LynchVesting of restricted stock unit awardsForm 144
3 September 2026McAnaney AdamOfficer9,092$285,9503 September 20269,092 shares from 3 September 2026Fidelity Brokerage Services LLCRestricted Stock VestingForm 144
3 September 2026Liang JanetOfficer10,360$325,8293 September 202610,360 shares from 3 September 2026Fidelity Brokerage Services LLCRestricted Stock VestingForm 144
3 September 2026Blackley Richard ScottOfficer28,869$907,9503 September 202628,869 shares from 3 September 2026Fidelity Brokerage Services LLCRestricted Stock VestingForm 144
3 September 2026Schlosser MarioOfficer, Director31,422$988,2443 September 202631,422 shares from 3 September 2026Fidelity Brokerage Services LLCRestricted Stock VestingForm 144
28 August 2026Schlosser MarioOfficer, Director150,000$4.6 million28 August 2026750,000 shares from 27 August 2026Fidelity Brokerage Services LLCStock Option ExerciseForm 144
27 August 2026Schlosser MarioOfficer, Director600,000$18.2 million27 August 2026None on Form 4 yetFidelity Brokerage Services LLCStock Option ExerciseForm 144
20 August 2026Jeffery H. BoydFormer Affiliate288,514$9.6 million20 August 2026None on Form 4 yetMorgan Stanley Smith Barney LLC Executive Financial ServicesPreviously Exercised OptionsForm 144
18 August 2026Richard Scott BlackleyOfficer - CFO18,750$614,25018 August 202618,750 shares from 18 August 2026Morgan StanleyRestricted stock units vesting under a registered planForm 144
13 August 2026Jeffery H. BoydFormer Affiliate288,513$8.7 million13 August 2026None on Form 4 yetMorgan Stanley Smith Barney LLC Executive Financial ServicesPreviously Exercised OptionsForm 144
10 August 2026Boyd Jeffery HFormer Director116,666$3.3 million10 August 2026None on Form 4 yetFidelity Brokerage Services LLCStock Option ExerciseForm 144
10 August 2026Jeffery H. BoydFormer Affiliate134,370$3.8 million10 August 2026None on Form 4 yetMorgan Stanley Smith Barney LLC Executive Financial ServicesRestricted Stock Vesting Under a Registered PlanForm 144
25 June 2026Mark BertoliniDirector, CEO2,776,937$83.1 million25 June 20262,445,306 shares from 25 June 2026Morgan Stanley Smith Barney LLCPerformance stock units; Restricted stock units vesting under a registered planForm 144
23 June 2026Siena Pizzo-Schlosser Dynasty TrustDirector50,000$1.4 million23 June 2026No matching Form 4 saleMorgan Stanley Smith Barney LLC Executive Financial ServicesGiftForm 144
23 June 2026Noah Pizzo-Schlosser Dynasty TrustDirector50,000$1.4 million23 June 2026No matching Form 4 saleMorgan Stanley Smith Barney LLC Executive Financial ServicesGiftForm 144
23 June 2026Pizzo-Schlosser Family Dynasty TrustDirector95,000$2.7 million23 June 2026No matching Form 4 saleMorgan Stanley Smith Barney LLC Executive Financial ServicesGiftForm 144
23 June 2026Mario SchlosserDirector880,000$25.1 million23 June 20261,075,000 shares from 23 June 2026Morgan Stanley Smith Barney LLC Executive Financial ServicesExercise of Stock Options; Previously Exercised Stock OptionsForm 144
2 June 2026Adam McAnaneyChief Legal Officer10,832$240,7952 June 20269,859 shares from 2 June 2026Morgan Stanley Smith Barney LLCRestricted stock units vesting under a registered planForm 144
2 June 2026Janet LiangPresident, Oscar Insurance13,706$304,6842 June 202612,475 shares from 2 June 2026Morgan Stanley Smith Barney LLCRestricted stock units vesting under a registered planForm 144
2 June 2026Richard Scott BlackleyCfo34,808$773,7822 June 202631,683 shares from 2 June 2026Morgan Stanley Smith Barney LLCRestricted stock units vesting under a registered planForm 144
2 June 2026Mario SchlosserDirector37,488$833,3582 June 202634,120 shares from 2 June 2026Morgan Stanley Smith Barney LLCRestricted stock units vesting under a registered planForm 144
18 May 2026Richard Scott BlackleyOfficer110,000$2.6 million18 May 2026110,000 shares from 18 May 2026Morgan Stanley Smith Barney LLC Executive Financial ServicesRestricted Stock UnitsForm 144
14 May 2026Richard Scott BlackleyOfficer100,000$2.4 million14 May 2026100,000 shares from 14 May 2026Morgan Stanley Smith Barney LLC Executive Financial ServicesRestricted Stock UnitsForm 144
2 March 2026Janet LiangPresident, Oscar Insurance6,468$88,3532 March 20267,453 shares from 2 March 2026Morgan Stanley Smith Barney LLCRestricted stock units vesting under a registered planForm 144
2 March 2026Adam McAnaneyChief Legal Officer15,530$212,1402 March 202618,710 shares from 2 March 2026Morgan Stanley Smith Barney LLCRestricted stock units vesting under a registered planForm 144
2 March 2026Blackley Richard ScottChief Financial Officer19,638$268,2552 March 202619,221 shares from 2 March 2026Morgan Stanley Smith Barney LLCRestricted stock units vesting under a registered planForm 144
2 March 2026Schlosser MarioOfficer / Director20,629$281,7922 March 202624,335 shares from 2 March 2026Morgan Stanley Smith Barney LLCRestricted stock units vesting under a registered planForm 144
6 January 2026Mario SchlosserDirector, Officer100,000$1.7 million6 January 2026196,928 shares from 5 January 2026Morgan Stanley Smith Barney LLC Executive Financial ServicesPreviously Exercised Stock OptionsForm 144
2 January 2026Mario SchlosserDirector, Officer216,396$3.1 million2 January 2026137,933 shares from 2 January 2026Morgan Stanley Smith Barney LLC Executive Financial ServicesPreviously Exercised Options; Restricted Stock UnitsForm 144
29 December 2025Mario SchlosserDirector, Officer57,300$850,33224 December 2025No matching Form 4 saleMorgan Stanley Smith Barney LLC Executive Financial ServicesOpen Market PurchaseForm 144
2 December 2025Adam McAnaneyChief Legal Officer2,123$35,5182 December 20251,852 shares from 2 December 2025Morgan Stanley Smith Barney LLCRestricted stock units vesting under a registered planForm 144
2 December 2025Janet LiangPresident, Oscar Insurance8,398$140,4992 December 20257,338 shares from 2 December 2025Morgan Stanley Smith Barney LLCRestricted stock units vesting under a registered planForm 144
2 December 2025Schlosser MarioOfficer / Director22,195$371,3222 December 202562,800 shares from 2 December 2025Morgan Stanley Smith Barney LLCRestricted stock units vesting under a registered planForm 144
2 December 2025Blackley Richard ScottChief Financial Officer28,737$480,7702 December 202525,135 shares from 2 December 2025Morgan Stanley Smith Barney LLCRestricted stock units vesting under a registered planForm 144
12 November 2025Mario T SchlosserOfficer, Director105,300$1.6 million12 November 2025No matching Form 4 saleMorgan Stanley Smith Barney LLC Executive Financial ServicesExercise of options under a registered planForm 144
12 November 2025Mario T SchlosserOfficer, Director286,182$4.4 million11 November 2025391,482 shares from 11 November 2025Morgan Stanley Smith Barney LLC Executive Financial ServicesExercise of options under a registered planForm 144
A Form 144 is the notice an insider files with the SEC before selling restricted or control shares over the Rule 144 thresholds; it says what may be sold, not what was.
Read moreValue is the filer's own aggregate market value. Sold, per Form 4: the same seller's open-market sales on Form 4 from the notice's date to 90 days after, added up, as they appear on the insiders page; a holder who files no Form 4, such as some large holders, never shows one. What is a Form 144?