Richard Scott Blackley

Oscar Health CFO Richard Scott Blackley sells 31.7K shares at $21.94 avg; scheduled 10b5-1 trade, pre-transaction holdings 1.11M shares

Richard Scott Blackley, Chief Financial Officer of Oscar Health, executed two separate sales totaling 31,683 shares for $695,162.09 on 2026-06-02 under a pre-arranged 10b5-1 trading plan. This represents a 2.9% reduction in his pre-transaction holdings of 1,106,660 shares. The sales are scheduled rather than discretionary, removing timing as a meaningful signal. Across his cross-ticker history, Blackley's 8 prior sells averaged a 90-day post-sale return of +1.6%, though measurable outcomes are not yet available for any of his 5 prior Oscar Health-specific trades. Oscar Health reported strong fundamentals with $4.6B quarterly revenue (+27.5% annual growth) and $679.0M net income, though the company remains unprofitable on a full-year basis.

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.

CFO Blackley Richard Scott sold 29,957 shares (30.0K) of Oscar Health at $17.06 on 2024-09-06 ($511.1K); stock down 25.0% from 52-week high.

Blackley Richard Scott, Chief Financial Officer of Oscar Health, sold 29,957 shares at $17.06 on 2024-09-06, reducing his holdings by 3.4% to 853,875 shares. This sale is notable in the context of recent price weakness: the stock has declined 25.0% from its 52-week high of $23.28 and is down 12.7% over the past 90 days. The CFO's recent transaction history at Oscar Health shows three additional sales executed on 2024-09-03 and 2024-09-04, suggesting a concentrated exit pattern over a compressed timeframe. While the company posted strong revenue growth of +47.9% year-over-year on $2.2B quarterly revenue, it remains unprofitable on a full-year basis, and the CFO's prior open-market sell at this ticker on 2024-06-06 was followed by a 10.9% decline at the 90-day mark.

Oscar Health CFO Blackley Richard Scott sold 131,859 shares for $2.3M across 3 separate transactions (Sept 3-4), reducing holdings 13.8%

Blackley Richard Scott, Chief Financial Officer of Oscar Health, executed 3 separate sales totaling 131,859 shares for $2,349,836.71 between September 3-4, 2024, at blended average price of $17.82. This represents a 13.8% reduction in his post-transaction holdings to 821,332 shares. The current stock price is $17.44, only 1.8% below the blended sale price. Notably, his prior sell at this ticker on 2024-06-06 produced a well-timed outcome, with the stock declining 10.9% over the subsequent 90 days; his cross-ticker sell history shows a 100.00% well-timed rate. The company is growing revenue at 47.9% annually and posted positive net income of $56,207,000.00 in the latest quarter, though it remains unprofitable on a full-year basis. The scale and pattern of insider selling merit observation against the company's profitability trajectory.