Safehold's top three insider shareholders as of September 29, 2026 are Jay Sugarman (Chairman And Ceo, 1.83Mn shares), Holdings Star (TenPercentOwner, 360.61K shares), Brett Asnas (Chief Financial Officer, 205.85K shares).
| # | Insider | Position | Direct | Indirect | Total | Share of Insiders | Last Filed |
|---|---|---|---|---|---|---|---|
| 1 | Jay Sugarman | Chairman And Ceo | 1,897,620 | 22,076 | 1,919,696 | 61.9% | 02 Apr, 2026 |
| 2 | Holdings Star | TenPercentOwner | 360,611 | 0 | 360,611 | 11.6% | 03 Apr, 2023 |
| 3 | Brett Asnas | Chief Financial Officer | 316,522 | 0 | 316,522 | 10.2% | 02 Apr, 2026 |
| 4 | Stefan M Selig | Director | 105,169 | 0 | 105,169 | 3.4% | 15 May, 2026 |
| 5 | Michael Lane Trachtenberg | President | 93,076 | 0 | 93,076 | 3.0% | 03 Dec, 2025 |
| 6 | Robin Josephs | Director | 90,708 | 0 | 90,708 | 2.9% | 11 Sep, 2026 |
| 7 | Barry W Ridings | Director | 64,747 | 0 | 64,747 | 2.1% | 17 Jul, 2026 |
| 8 | Private Ltd Gic | Director | 0 | 56,668 | 56,668 | 1.8% | 04 Apr, 2023 |
| 9 | Jay S Nydick | Director | 47,336 | 0 | 47,336 | 1.5% | 15 May, 2026 |
| 10 | Marcos Alvarado | President Cio | 25,754 | 0 | 25,754 | 0.8% | 31 Mar, 2023 |
| 11 | Christopher Michael Uhlick | Chief Accounting Officer | 12,483 | 0 | 12,483 | 0.4% | 01 Jun, 2026 |
| 12 | Garett Rosenblum | Chief Accounting Officer | 3,430 | 0 | 3,430 | 0.1% | 31 Mar, 2023 |
| 13 | Clifford Desouza | Director | 2,877 | 47 | 2,924 | 0.1% | 04 Apr, 2023 |
| 14 | David Eisenberg | Director | 1,148 | 0 | 1,148 | 0.0% | 23 Jan, 2023 |
| 15 | Richard J Lieb | Director | 263 | 0 | 263 | 0.0% | 04 Apr, 2023 |
Each row is that insider’s most recently reported position, from Form 4 filings over the last 60 months — which is why this total does not tie to the quarterly series above, where a quarter counts only the insiders who filed in it. Shares held through a fund or institutional portfolio are counted on the institutional ownership page instead.
| Date | Insider | Position | Transaction | Shares | Price | Value | Shares Held After | Ownership |
|---|---|---|---|---|---|---|---|---|
| 09 Sep, 2026 | Robin Josephs | Director | Disposed S | 9,500 | $14.56 | $138.35K | 89,068 | Direct |
| 15 Jul, 2026 | Barry W Ridings | Director | Acquired A | 30 | $0.00 | $0 | 61,725 | Direct |
| 15 Jul, 2026 | Robin Josephs | Director | Acquired A | 335 | $0.00 | $0 | 98,568 | Direct |
| 29 May, 2026 | Christopher Michael Uhlick | Chief Accounting Officer | Acquired A | 4,500 | $0.00 | $0 | 12,483 | Direct |
| 14 May, 2026 | Jay S Nydick | Director | Acquired A | 8,778 | $0.00 | $0 | 47,336 | Direct |
| 14 May, 2026 | Stefan M Selig | Director | Acquired A | 13,655 | $0.00 | $0 | 105,169 | Direct |
| 14 May, 2026 | Barry W Ridings | Director | Acquired A | 8,778 | $0.00 | $0 | 61,695 | Direct |
| 14 May, 2026 | Robin Josephs | Director | Acquired A | 8,778 | $0.00 | $0 | 98,233 | Direct |
| 15 Apr, 2026 | Robin Josephs | Director | Acquired A | 359 | $0.00 | $0 | 89,455 | Direct |
| 15 Apr, 2026 | Barry W Ridings | Director | Acquired A | 33 | $0.00 | $0 | 52,917 | Direct |
| 31 Mar, 2026 | Jay Sugarman | Chairman And Ceo | Disposed F | 23,662 | $0.00 | $0 | 1,830,283 | Direct |
| 31 Mar, 2026 | Brett Asnas | Chief Financial Officer | Disposed F | 8,118 | $0.00 | $0 | 205,849 | Direct |
| 27 Feb, 2026 | Brett Asnas | Chief Financial Officer | Acquired A | 66,171 | $0.00 | $0 | 213,966 | Direct |
| 27 Feb, 2026 | Jay Sugarman | Chairman And Ceo | Acquired A | 90,149 | $0.00 | $0 | 1,853,946 | Direct |
| 27 Feb, 2026 | Brett Asnas | Chief Financial Officer | Disposed F | 27,295 | $0.00 | $0 | 213,966 | Direct |
| 27 Feb, 2026 | Jay Sugarman | Chairman And Ceo | Disposed F | 40,825 | $0.00 | $0 | 1,853,946 | Direct |
| 15 Jan, 2026 | Barry W Ridings | Director | Acquired A | 33 | $0.00 | $0 | 52,884 | Direct |
| 15 Jan, 2026 | Robin Josephs | Director | Acquired A | 362 | $0.00 | $0 | 89,096 | Direct |
| 01 Dec, 2025 | Michael Lane Trachtenberg | President | Acquired A | 93,076 | $0.00 | $0 | 93,076 | Direct |
| 15 Oct, 2025 | Barry W Ridings | Director | Acquired A | 32 | $0.00 | $0 | 52,851 | Direct |