OSCR Oscar Health, Inc. Insider Trading

Director Mario Schlosser sells 47,500 OSCR shares for $1,484,013.80 via pre-arranged 10b5-1 plan on July 1, 2026

Director Mario Schlosser executed 3 separate sales totaling 47,500 shares for $1,484,013.80 on 2026-07-01 via a pre-arranged 10b5-1 trading plan adopted on 2026-03-24. His non-derivative holdings in the form of Class B Common Stock (held through the Pizzo-Schlosser Family Dynasty Trust) were reduced to zero shares post-transaction, though his overall beneficial position remains significant at 538,333 shares held through derivative securities in the trust vehicle. The stock is trading at $31.44 currently, near its 52-week high of $33.10 (+28.3% over 30 days and +142.4% over 90 days), suggesting the company has appreciated substantially since the plan was adopted. Because this sale is part of a scheduled 10b5-1 plan—not a discretionary decision—timing inferences are not applicable; however, the context of strong recent price performance and the company's reported $4.6B in quarterly revenue with $679.0M net income (against a history of full-year unprofitability) indicates Oscar Health has achieved material operational improvement that likely drove the recent rally.

Oscar Health Director Mario Schlosser executes 12 scheduled sales totaling 1,027,500 shares for $30.2M near 52-week high

Mario Schlosser, Director at Oscar Health (OSCR), executed 12 separate sales on 2026-06-23 totaling 1,027,500 shares for $30,183,413.04 at a blended average price of $29.38, under a 10b5-1 trading plan adopted on 2026-03-24. These transactions cleared his Table I non-derivative holdings, but substantial derivative and Class B positions remain across 6 ownership vehicles totaling 8,197,085 shares, including 3,740,000 stock options and multiple Class B Common Stock tranches. The stock had risen +31.0% over the prior 30 days and +157.4% over 90 days, sitting -5.6% from its 52-week high of $30.38 at the time of the sales. His 5 prior sells at OSCR showed subsequent 90-day returns ranging from -25.0% to -14.4% across four of those trades, with the most recent showing -25.0%, though those were not necessarily executed under a scheduled plan as this filing is.

CFO Blackley Richard Scott sold 110,000 shares of OSCR at $25.03 on 2026-05-18 per 10b5-1 plan; stock up 70.6% in 90 days

Blackley Richard Scott, CFO of Oscar Health, sold 110,000 shares (110.0K shares) for $2,753,300.00 ($2.8M) on 2026-05-18 under a pre-arranged 10b5-1 trading plan adopted on 2026-02-12, leaving him with 1,106,660 shares (1.11M shares) post-transaction. The sale occurred when OSCR was trading at $25.03, near its 52-week high of $25.58, and follows a strong 70.6% 90-day run and 42.5% 30-day surge. Because this transaction is scheduled under a 10b5-1 plan rather than discretionary, the timing reflects pre-set mechanics rather than an active trading decision. His prior open-market sells (5 trades across all tickers) averaged +7.7% 30-day returns and -1.7% 90-day returns, suggesting a historical pattern where post-sale price action has drifted lower on the 90-day horizon; at the specific ticker OSCR, his 5 prior sales showed mixed outcomes ranging from -14.3% to +18.0% over 30 days. The company fundamentals show $4,647,194,000.00 ($4.6B) revenue (latest quarter) with 27.5% annual growth, but net income of $678,996,000.00 ($679.0M) came in a period when full-year profitability was negative.

CFO Blackley Richard Scott sold 100,000 OSCR shares at $23.16 blended average on 2026-05-14 via scheduled 10b5-1 plan, retaining 1.22M shares.

Chief Financial Officer Blackley Richard Scott executed 2 separate sales totaling 100,000 shares for $2,316,031.29 on 2026-05-14 under a 10b5-1 trading plan adopted on 2026-02-12—a scheduled, non-discretionary transaction. The sale reduced his holdings by 7.6% to 1.22M shares. Because this trade is governed by a pre-arranged plan, no timing-based inference about conviction or market outlook is warranted. His prior sales at Oscar Health have shown mixed retrospective outcomes: 30-day returns ranging from −14.3% to +18.0%, and 90-day returns from −10.9% to +3.0%. The company reported $4.6B in quarterly revenue and $679.0M in net income for the latest quarter, though it remains unprofitable on a full-year basis despite +27.5% annual revenue growth. Current price of $25.30 lies 4.2% above the 52-week high of $24.28, representing a 60.2% gain over the prior 30 days.

CEO Mark T Bertolini buys 1,000,000 shares of OSCR at $11.92, increasing stake 10.9%; stock down 42.3% from 52-week high.

Bertolini's purchase of 1,000,000 shares at $11.92 represents a material addition to his stake (10.9% increase from 9,196,876 to 10,196,876 shares), executed while OSCR trades 42.3% below its 52-week high of $22.47 and has declined 21.3% over the past 90 days. The company's fundamentals remain mixed: revenue reached $3.0B with strong 27.5% year-over-year growth, but Oscar Health remains unprofitable with net income of $-137.4M in the latest full fiscal year. The timing and scale of a CEO's open-market share purchase warrant investor attention given the stock's recent underperformance, though the purchase itself offers no direct insight into management's forward expectations without additional context about capital allocation strategy or stated rationale.

OSCR President of Technology Mario Schlosser sells 76,962 shares at $17.01; stock now -24.8% from 52-week high with -10.0% 90-day decline.

Mario Schlosser, President of Technology & CTO, sold 76,962 shares at $17.01 on 2026-01-06, reducing his holdings from 427,142 to 350,180 shares. The sale occurred as Oscar Health stock trades at $16.90, down 24.8% from its 52-week high and down 10.0% over the past 90 days. Notably, Schlosser has executed three separate sales in the past two weeks (2025-12-24, 2026-01-02, and 2026-01-06), suggesting sustained portfolio activity during a period of stock weakness. His cross-ticker track record shows a 66.67% well-timed sell rate with strong average 90-day returns of +38.8%, but this pattern does not apply to his recent Oscar Health activity where prior measurable outcomes have been mixed or not yet complete.

Oscar Health CTO Mario Schlosser sold 234,861 shares for $3,587,707.58 in two transactions Jan 2–5, reducing stake by 40.1%

Mario Schlosser (President of Technology & CTO) sold 234.9K shares across 2 separate transactions—137,933 shares at $15.02 on 2026-01-02 and 96,928 shares at $15.64 on 2026-01-05—for combined proceeds of $3.6M and a blended average price of $15.28. This reduces his position from 585.0K to 350.2K shares (-40.1% reduction). The current price of $16.52 is 26.5% below the 52-week high of $22.47, and Oscar's stock has fallen 24.2% over the past 90 days and 1.5% in the past 30 days. His cross-ticker track record shows 7 prior sells with an average 90-day return of +38.8% and a 90-day well-timed rate of 66.67%, indicating his sells have historically preceded price appreciation. At Oscar specifically, the measurable outcome from his prior sale on 2025-09-22 showed a 90-day return of -19.2% (well-timed), though only 1 of 1 prior Oscar sales have a measurable 90-day outcome. The company posted $3.0B in quarterly revenue and $-137.4M net loss, with a P/E of 150.18, reflecting unprofitability despite strong 56.5% annual revenue growth.

CTO Schlosser sold 38,835 shares of OSCR at $15.00; stock now down 35.4% from 52-week high and 19.2% in 30 days.

Schlosser Mario, President of Technology & CTO, sold 38,835 shares at $15.00 on 2025-12-24, reducing his OSCR holdings by 8.1%. The sale price of $15.00 sits above the current price of $14.51, but the stock has declined 35.4% from its 52-week high of $22.47 and dropped 19.2% over the past 30 days alone. At the same-ticker level, his prior 3 completed trades showed mixed outcomes: two were well-timed by the 90-day measure (30 Sep 2025 sale: 90d return -19.2%; 16 Nov 2023 sale: 90d return +137.3%), while one was poorly timed (15 Aug 2023 sale: 90d return -1.6%). The company reports a P/E of 131.91 and is unprofitable, with a net loss of $-137,450,000.00 in the latest quarter, despite strong 56.5% annual revenue growth. The timing of this December sale, occurring after the stock has already experienced material 30- and 90-day declines, limits the strength of any signal this transaction may convey about near-term confidence levels.

Co-founder Joshua Kushner buys 188,395 shares in 2 transactions at $16.97–$16.86, spending $3.2M as stock trades 31.4% below 52-week high.

Joshua Kushner, Co-Founder and Vice Chairman, purchased 188,395 shares across two separate transactions on 2024-11-20 and 2024-11-21 at a blended average price of $16.91, for a total outlay of $3,185,680.73. This purchase increased his holdings from 6,155,222 shares to 6,343,617 shares, a net addition of 3.1% to his pre-transaction position. The timing is notable: Oscar Health's stock is currently trading at $15.98, representing a -31.4% drawdown from its 52-week high of $23.28, and the company is unprofitable with net income of $-54,596,000.00 over its most recent full fiscal year, despite strong revenue growth of 47.9%. Over the preceding week (2024-11-11 through 2024-11-14), Kushner had already executed five separate buy transactions at this ticker, establishing a concentrated pattern of accumulation during a period of stock weakness. His cross-ticker open-market track record shows 5 prior buys, and none of his same-ticker purchases yet have measurable 90-day outcomes, leaving his historical execution accuracy at Oscar Health unestablished.

Thrive Partners VII Growth GP bought 188,395 OSCR shares for $3.2M at $16.91 avg over two days as stock down 31.4% from 52-week high

Thrive Partners VII Growth GP completed 2 separate purchases totaling 188,395 shares for $3,185,680.73 at a blended average price of $16.91, increasing holdings from 6.16M to 6.34M shares (+3.1%). The transaction occurred as Oscar Health trades 31.4% below its 52-week high of $23.28, despite strong 47.9% annual revenue growth; however, the company remains unprofitable with negative $54.6M net income over the most recent full fiscal year. The timing coincides with a recent pattern of sustained buying by this insider—5 prior trades at Oscar Health occurred between 2024-11-11 and 2024-11-14, all outcomes not yet measurable. The blended transaction price of $16.91 sits above the current market price of $15.98, creating immediate unrealized loss on this filing's purchases.