Oscar Health Inc
NYSE: OSCR · HEALTHCARE · HEALTHCARE PLANS
Updated 2026-06-05
Oscar Health Inc (OSCR) Insider transactions
All transactions
| Date | Insider | Title | Type | Shares | Price | Value |
|---|---|---|---|---|---|---|
| 2026-06-04 | WITTMAN, VANESSA AMES | Director | Buy | 8,475 | — | — |
| 2026-06-04 | SANKARAN, SID | Director | Buy | 8,475 | — | — |
| 2026-06-04 | PLOUFFE, DAVID | Director | Buy | 8,475 | — | — |
| 2026-06-04 | LANG, LAURA W | Director | Buy | 8,475 | — | — |
| 2026-06-04 | GASSEN, WILLIAM | Director | Buy | 8,475 | — | — |
| 2026-06-02 | SCHLOSSER, MARIO | Director | Sale | 24,452 | $21.74 | $531586.48 |
| 2026-06-02 | SCHLOSSER, MARIO | Director | Sale | 9,668 | $22.45 | $217046.60 |
| 2026-06-02 | MCANANEY, ADAM | Chief Legal Officer | Sale | 7,065 | $21.74 | $153593.10 |
| 2026-06-02 | MCANANEY, ADAM | Chief Legal Officer | Sale | 2,794 | $22.45 | $62725.30 |
| 2026-06-02 | LIANG, JANET | President, Oscar Insurance | Sale | 8,940 | $21.74 | $194355.60 |
| 2026-06-02 | LIANG, JANET | President, Oscar Insurance | Sale | 3,535 | $22.45 | $79360.75 |
| 2026-06-02 | BLACKLEY, RICHARD SCOTT | Chief Financial Officer | Sale | 22,706 | $21.74 | $493628.44 |
| 2026-06-02 | BLACKLEY, RICHARD SCOTT | Chief Financial Officer | Sale | 8,977 | $22.45 | $201533.65 |
| 2026-06-02 | BALTRUS, VICTORIA | Chief Accounting Officer | Sale | 1,091 | $21.74 | $23718.34 |
| 2026-06-02 | BALTRUS, VICTORIA | Chief Accounting Officer | Sale | 432 | $22.45 | $9698.40 |
| 2026-05-18 | BLACKLEY, RICHARD SCOTT | Chief Financial Officer | Sale | 110,000 | $25.03 | $2.75M |
| 2026-05-14 | BLACKLEY, RICHARD SCOTT | Chief Financial Officer | Sale | 91,259 | $23.10 | $2.11M |
| 2026-05-14 | BLACKLEY, RICHARD SCOTT | Chief Financial Officer | Sale | 8,741 | $23.79 | $207948.39 |
| 2026-04-09 | SANKARAN, SID | Director | Buy | 1,203 | $14.54 | $17491.62 |
| 2026-04-09 | PLOUFFE, DAVID | Director | Buy | 1,461 | $14.54 | $21242.94 |
| 2026-04-09 | GASSEN, WILLIAM | Director | Buy | 1,418 | $14.54 | $20617.72 |
| 2026-04-09 | BOYD, JEFFERY H | Director | Buy | 3,610 | $14.54 | $52489.40 |
| 2026-04-06 | BERTOLINI, MARK T | Director, Chief Executive Officer | Sale | 1,000,001 | $11.92 | $11.92M |
| 2026-04-06 | BERTOLINI, MARK T | Director, Chief Executive Officer | Buy | 1,000,000 | $11.92 | $11.92M |
| 2026-04-03 | BERTOLINI, MARK T | Director, Chief Executive Officer | Sale | 5,733,334 | — | — |
| 2026-04-03 | BERTOLINI, MARK T | Director, Chief Executive Officer | Buy | 5,733,334 | — | — |
| 2026-03-12 | BLACKLEY, RICHARD SCOTT | Chief Financial Officer | Buy | 75,000 | — | — |
| 2026-03-02 | SCHLOSSER, MARIO | Director, President of Technology & CTO | Buy | 189,141 | — | — |
| 2026-03-02 | SCHLOSSER, MARIO | Director, President of Technology & CTO | Sale | 24,335 | $13.39 | $325845.65 |
| 2026-03-02 | MCANANEY, ADAM | Chief Legal Officer | Buy | 67,424 | — | — |
| 2026-03-02 | MCANANEY, ADAM | Chief Legal Officer | Sale | 18,710 | $13.39 | $250526.90 |
| 2026-03-02 | LIANG, JANET | President, Oscar Insurance | Buy | 106,458 | — | — |
| 2026-03-02 | LIANG, JANET | President, Oscar Insurance | Sale | 7,453 | $13.39 | $99795.67 |
| 2026-03-02 | BLACKLEY, RICHARD SCOTT | Chief Financial Officer | Buy | 134,847 | — | — |
| 2026-03-02 | BLACKLEY, RICHARD SCOTT | Chief Financial Officer | Sale | 19,221 | $13.39 | $257369.19 |
| 2026-03-02 | BERTOLINI, MARK T | Director, Chief Executive Officer | Buy | 1,596,877 | — | — |
| 2026-03-02 | BALTRUS, VICTORIA | Chief Accounting Officer | Buy | 17,300 | — | — |
| 2026-03-02 | BALTRUS, VICTORIA | Chief Accounting Officer | Sale | 4,638 | $13.39 | $62102.82 |
| 2026-01-08 | SCHLOSSER, MARIO | Director, President of Technology & CTO | Sale | 23,038 | — | — |
| 2026-01-08 | SCHLOSSER, MARIO | Director, President of Technology & CTO | Buy | 23,038 | — | — |
| 2026-01-08 | PLOUFFE, DAVID | Director | Buy | 1,257 | $16.90 | $21243.30 |
| 2026-01-08 | GASSEN, WILLIAM | Director | Buy | 1,220 | $16.90 | $20618.00 |
| 2026-01-08 | BOYD, JEFFERY H | Director | Buy | 3,106 | $16.90 | $52491.40 |
| 2026-01-06 | SCHLOSSER, MARIO | Director, President of Technology & CTO | Sale | 76,962 | — | — |
| 2026-01-06 | SCHLOSSER, MARIO | Director, President of Technology & CTO | Sale | 76,962 | $17.01 | $1.31M |
| 2026-01-05 | SCHLOSSER, MARIO | Director, President of Technology & CTO | Sale | 86,893 | — | — |
| 2026-01-05 | SCHLOSSER, MARIO | Director, President of Technology & CTO | Sale | 96,928 | $15.64 | $1.52M |
| 2026-01-05 | SCHLOSSER, MARIO | Director, President of Technology & CTO | Buy | 86,893 | — | — |
| 2026-01-02 | SCHLOSSER, MARIO | Director, President of Technology & CTO | Sale | 59,800 | — | — |
| 2026-01-02 | SCHLOSSER, MARIO | Director, President of Technology & CTO | Sale | 137,933 | $15.02 | $2.07M |
| 2026-01-02 | SCHLOSSER, MARIO | Director, President of Technology & CTO | Buy | 59,800 | — | — |
| 2025-12-24 | SCHLOSSER, MARIO | Director, President of Technology & CTO | Sale | 38,835 | $15.00 | $582525.00 |
| 2025-12-02 | SCHLOSSER, MARIO | Director, President of Technology & CTO | Sale | 23,965 | $16.59 | $397579.35 |
| 2025-12-02 | MCANANEY, ADAM | Chief Legal Officer | Sale | 1,852 | $16.59 | $30724.68 |
| 2025-12-02 | LIANG, JANET | President, Oscar Insurance | Sale | 7,338 | $16.59 | $121737.42 |
| 2025-12-02 | BLACKLEY, RICHARD SCOTT | Chief Financial Officer | Sale | 25,135 | $16.59 | $416989.65 |
| 2025-12-02 | BALTRUS, VICTORIA | Chief Accounting Officer | Sale | 4,149 | $16.59 | $68831.91 |
| 2025-11-12 | SCHLOSSER, MARIO | Director, President of Technology & CTO | Sale | 141,330 | — | — |
| 2025-11-12 | SCHLOSSER, MARIO | Director, President of Technology & CTO | Buy | 141,330 | $6.36 | $898858.80 |
| 2025-11-12 | SCHLOSSER, MARIO | Director, President of Technology & CTO | Sale | 105,300 | — | — |
| 2025-11-12 | SCHLOSSER, MARIO | Director, President of Technology & CTO | Buy | 105,300 | — | — |
| 2025-11-11 | SCHLOSSER, MARIO | Director, President of Technology & CTO | Sale | 413,835 | — | — |
| 2025-11-11 | SCHLOSSER, MARIO | Director, President of Technology & CTO | Buy | 413,835 | $6.36 | $2.63M |
| 2025-11-11 | SCHLOSSER, MARIO | Director, President of Technology & CTO | Sale | 286,182 | — | — |
| 2025-11-11 | SCHLOSSER, MARIO | Director, President of Technology & CTO | Sale | 286,182 | $15.27 | $4.37M |
| 2025-10-09 | PLOUFFE, DAVID | Director | Buy | 1,034 | $20.54 | $21238.36 |
| 2025-10-09 | GASSEN, WILLIAM | Director | Buy | 1,004 | $20.54 | $20622.16 |
| 2025-10-09 | BOYD, JEFFERY H | Director | Buy | 2,555 | $20.54 | $52479.70 |
| 2025-09-22 | SCHLOSSER, MARIO | Director, President of Technology & CTO | Sale | 555,165 | — | — |
| 2025-09-22 | SCHLOSSER, MARIO | Director, President of Technology & CTO | Buy | 555,165 | $6.36 | $3.53M |
| 2025-09-22 | SCHLOSSER, MARIO | Director, President of Technology & CTO | Sale | 395,000 | — | — |
| 2025-09-22 | SCHLOSSER, MARIO | Director, President of Technology & CTO | Buy | 395,000 | — | — |
| 2025-09-02 | SCHLOSSER, MARIO | Director, President of Technology & CTO | Sale | 23,879 | $16.66 | $397824.14 |
| 2025-09-02 | MCANANEY, ADAM | Chief Legal Officer | Sale | 1,845 | $16.66 | $30737.70 |
| 2025-09-02 | LIANG, JANET | President, Oscar Insurance | Sale | 7,303 | $16.66 | $121667.98 |
| 2025-09-02 | BLACKLEY, RICHARD SCOTT | Chief Financial Officer | Sale | 28,166 | $16.66 | $469245.56 |
| 2025-09-02 | BALTRUS, VICTORIA | Chief Accounting Officer | Sale | 6,266 | $16.66 | $104391.56 |
| 2025-07-10 | PLOUFFE, DAVID | Director | Buy | 1,368 | $15.53 | $21245.04 |
| 2025-07-10 | GASSEN, WILLIAM | Director | Buy | 1,215 | $15.53 | $18868.95 |
| 2025-07-10 | BOYD, JEFFERY H | Director | Buy | 3,380 | $15.53 | $52491.40 |
| 2025-06-04 | WITTMAN, VANESSA AMES | Director | Buy | 14,134 | — | — |
| 2025-06-04 | SANKARAN, SID | Director | Buy | 14,134 | — | — |
| 2025-06-04 | PLOUFFE, DAVID | Director | Buy | 14,134 | — | — |
| 2025-06-04 | LANG, LAURA W | Director | Buy | 14,134 | — | — |
| 2025-06-04 | GASSEN, WILLIAM | Director | Buy | 14,134 | — | — |
| 2025-06-04 | BOYD, JEFFERY H | Director | Buy | 14,134 | — | — |
| 2025-06-02 | SCHLOSSER, MARIO | Director, President of Technology & CTO | Sale | 23,879 | $13.80 | $329530.20 |
| 2025-06-02 | MCANANEY, ADAM | Chief Legal Officer | Sale | 1,847 | $13.80 | $25488.60 |
| 2025-06-02 | LIANG, JANET | President, Oscar Insurance | Sale | 7,196 | $13.80 | $99304.80 |
| 2025-06-02 | BLACKLEY, RICHARD SCOTT | Chief Financial Officer | Sale | 28,185 | $13.80 | $388953.00 |
| 2025-06-02 | BALTRUS, VICTORIA | Chief Accounting Officer | Sale | 6,265 | $13.80 | $86457.00 |
| 2025-05-12 | ROBINSON, ELBERT O. JR. | Director | Sale | 25,000 | $16.43 | $410750.00 |
| 2025-04-10 | PLOUFFE, DAVID | Director | Buy | 1,734 | $12.25 | $21241.50 |
| 2025-04-10 | GASSEN, WILLIAM | Director | Buy | 1,530 | $12.25 | $18742.50 |
| 2025-04-10 | BOYD, JEFFERY H | Director | Buy | 4,285 | $12.25 | $52491.25 |
| 2025-04-03 | BERTOLINI, MARK T | Director, Chief Executive Officer | Sale | 955,556 | — | — |
| 2025-04-03 | BERTOLINI, MARK T | Director, Chief Executive Officer | Buy | 955,556 | — | — |
| 2025-03-05 | SCHLOSSER, MARIO | Director, President of Technology & CTO | Buy | 172,269 | — | — |
| 2025-03-05 | MCANANEY, ADAM | Chief Legal Officer | Buy | 61,409 | — | — |
| 2025-03-05 | LIANG, JANET | President, Oscar Insurance | Buy | 96,962 | — | — |
Frequently asked questions
Are OSCR insiders buying or selling?
Over the transactions on record, OSCR insiders have been net sellers, with about $33.30M in stock sold across 52 sales, against 20 open-market purchases.
Does insider selling at OSCR mean the stock will fall?
Not by itself. Most executive selling is pre-scheduled through 10b5-1 plans filed months in advance, and insiders sell for diversification, taxes, and liquidity far more often than out of any view on the price. Insider buying is the stronger signal, especially when several insiders buy around the same time, because there is usually only one reason to put personal cash into the stock.
Which OSCR insiders are selling the most?
Recent selling is concentrated in a few names. SCHLOSSER, MARIO accounts for the largest share on record, with about $12.05M sold. Selling by one or two individuals matters less than broad selling across the whole leadership team, which is the pattern worth watching.