Updated Jul 16, 2026
PITTMAN ROBERT W has filed 1 SEC Form 4 filing across 1 company in the last 90 days — buying. Lifetime open-market purchases: $655K. Historical track record: 4/5 stars across 4 tracked purchases.

Robert W. Pittman is an American media executive best known for leadership roles in radio, television, and digital media. He is widely recognized for his earlier leadership of MTV Networks and has served as Chairman and Chief Executive Officer of iHeartMedia, Inc., guiding the company through diversification beyond traditional radio into digital media and live entertainment. Pittman is a prominent figure in the media industry with decades of influence across multiple platforms and business models.
| Role | Insider |
|---|---|
| Notability | 85/100 |
| Links | Wikipedia |
InsiderAlpha computes a forward-return-based score for every insider with enough Form 4 purchase history. The metrics below reflect realised performance after each tracked open-market purchase.
| InsiderAlpha rating | ★★★★☆ (4/5) |
|---|---|
| Total purchases tracked | 4 |
| Purchases with forward-return data | 4 |
| 30-day win rate | 7500% |
| 90-day win rate | 10000% |
| Avg 5-day return | -179.25% |
| Avg 30-day return | +1881.46% |
| Avg 90-day return | +5408.02% |
| Best 30-day return | +3412.70% |
| Date | Ticker | Company | Code | Shares | Price | Value |
|---|---|---|---|---|---|---|
| 2026-05-20 | IHRT | iHeartMedia, Inc. | F — Tax withholding / forfeiture | 555.0K | $5.18 | $2.87M |
| 2026-05-20 | IHRT | iHeartMedia, Inc. | D — Derivative transaction | 302.1K | $5.18 | $1.57M |
| 2026-05-20 | IHRT | iHeartMedia, Inc. | F — Tax withholding / forfeiture | 226.6K | $5.18 | $1.17M |
| 2026-05-20 | IHRT | iHeartMedia, Inc. | M — Option exercise | 528.8K | — | |
| 2026-03-10 | IHRT | iHeartMedia, Inc. | P — Open-market purchase | 16.3K | $2.97 | $49K |
| 2026-03-05 | IHRT | iHeartMedia, Inc. | P — Open-market purchase | 32.5K | $3.25 | $106K |
| 2026-02-28 | IHRT | iHeartMedia, Inc. | F — Tax withholding / forfeiture | 50.0K | $3.17 | $159K |
| 2026-02-28 | IHRT | iHeartMedia, Inc. | D — Derivative transaction | 146.7K | $3.17 | $465K |
| 2026-02-28 | IHRT | iHeartMedia, Inc. | F — Tax withholding / forfeiture | 110.0K | $3.17 | $349K |
| 2026-02-28 | IHRT | iHeartMedia, Inc. | M — Option exercise | 256.7K | — | |
| 2026-02-21 | IHRT | iHeartMedia, Inc. | F — Tax withholding / forfeiture | 53.6K | $3.61 | $194K |
| 2026-02-21 | IHRT | iHeartMedia, Inc. | D — Derivative transaction | 173.2K | $3.61 | $625K |
| 2026-02-21 | IHRT | iHeartMedia, Inc. | F — Tax withholding / forfeiture | 129.9K | $3.61 | $469K |
| 2026-02-21 | IHRT | iHeartMedia, Inc. | M — Option exercise | 303.0K | — | |
| 2026-02-19 | IHRT | iHeartMedia, Inc. | A — Grant or award | 500.0K | $0.00 | |
| 2026-02-19 | IHRT | iHeartMedia, Inc. | A — Grant or award | 278.3K | $0.00 | |
| 2026-02-19 | IHRT | iHeartMedia, Inc. | A — Grant or award | 949.3K | $0.00 | |
| 2025-08-14 | IHRT | iHeartMedia, Inc. | P — Open-market purchase | 117.4K | $2.19 | $257K |
| 2025-05-15 | IHRT | iHeartMedia, Inc. | P — Open-market purchase | 200.0K | $1.22 | $244K |
| 2025-02-25 | IHRT | iHeartMedia, Inc. | D — Derivative transaction | 80.6K | $1.24 | $100K |
Robert W. Pittman is an American media executive best known for leadership roles in radio, television, and digital media. He is widely recognized for his earlier leadership of MTV Networks and has served as Chairman and Chief Executive Officer of iHeartMedia, Inc., guiding the company through diversification beyond traditional radio into digital media and live entertainment. Pi…
1 primary Form 4 filings in the last 90 days, covering 1 company.
Recorded transactions: 4 open-market purchases ($655K) and 0 open-market sales () across all tracked filings.
Across 4 tracked purchases, PITTMAN ROBERT W averaged +1881.5% avg 30-day return with a 7500% 30-day win rate. InsiderAlpha rates the track record at 4/5 stars.
All Form 4 filings, transaction values, and 10b5-1 plan flags are listed on this page and updated in real time as new SEC EDGAR filings are processed.
Open the live PITTMAN ROBERT W profile on InsiderAlpha for real-time alerts, AI-scored trade ideas, and full transaction history.