Rli's three largest insider shareholders as of September 29, 2026 are Jonathan E Michael (Chairman Ceo, 7.43Mn shares), John Thomas Baily (Director, 478.28K shares), Michael J Stone (Director, 433.32K shares).
| # | Insider | Position | Direct | Indirect | Total | Share of Insiders | Last Filed |
|---|---|---|---|---|---|---|---|
| 1 | Jonathan E Michael | Chairman Ceo | 7,432,611 | 0 | 7,432,611 | 77.4% | 26 Feb, 2024 |
| 2 | John Thomas Baily | Director | 0 | 478,281 | 478,281 | 5.0% | 12 May, 2023 |
| 3 | Michael J Stone | Director | 433,316 | 0 | 433,316 | 4.5% | 15 May, 2026 |
| 4 | Todd Wayne Bryant | Chief Financial Officer | 352,430 | 0 | 352,430 | 3.7% | 13 Nov, 2024 |
| 5 | Craig W Kliethermes | Chief Executive Officer | 153,990 | 0 | 153,990 | 1.6% | 03 Jun, 2026 |
| 6 | Jeffrey D Fick | Chief Legal Officer Corp Sec | 142,061 | 0 | 142,061 | 1.5% | 27 Jan, 2025 |
| 7 | Jordan W Graham | Director | 0 | 118,176 | 118,176 | 1.2% | 15 May, 2026 |
| 8 | Calvin Jr Butler | Director | 0 | 109,813 | 109,813 | 1.1% | 23 Feb, 2023 |
| 9 | Jennifer L Klobnak | Chief Operating Officer | 104,318 | 0 | 104,318 | 1.1% | 28 May, 2026 |
| 10 | Aaron Paul Diefenthaler | Treasurer, Chief Invest. Off. | 71,763 | 0 | 71,763 | 0.7% | 26 Nov, 2025 |
| 11 | Kaj Ahlmann | Director | 40,978 | 0 | 40,978 | 0.4% | 06 May, 2024 |
| 12 | Seth Anthony Davis | Vice President, Controller | 30,945 | 0 | 30,945 | 0.3% | 06 May, 2026 |
| 13 | Debbie Sharell Roberts | Director | 0 | 30,402 | 30,402 | 0.3% | 03 Aug, 2026 |
| 14 | Robert P Jr Restrepo | Director | 26,501 | 0 | 26,501 | 0.3% | 15 May, 2026 |
| 15 | Michael E Angelina | Director | 25,585 | 0 | 25,585 | 0.3% | 15 May, 2026 |
| 16 | Susan S. Fleming | Director | 0 | 22,674 | 22,674 | 0.2% | 15 May, 2026 |
| 17 | Paul Bennett Medini | Director | 0 | 9,932 | 9,932 | 0.1% | 03 Aug, 2026 |
| 18 | David B. Duclos | Director | 9,780 | 0 | 9,780 | 0.1% | 29 May, 2026 |
| 19 | Clark C Kellogg | Director | 4,502 | 0 | 4,502 | 0.0% | 01 Jun, 2026 |
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 |
|---|---|---|---|---|---|---|---|---|
| 13 Aug, 2026 | James Henderson Bradshaw | Director | Acquired A | 2,153 | $0.00 | $0 | 2,153 | Direct |
| 03 Aug, 2026 | Jennifer L Klobnak | Chief Operating Officer | Acquired A | 12,500 | $0.00 | $0 | 12,500 | Direct |
| 03 Aug, 2026 | Seth Anthony Davis | Vice President, Controller | Acquired A | 1,500 | $0.00 | $0 | 1,500 | Direct |
| 03 Aug, 2026 | Craig W Kliethermes | Chief Executive Officer | Acquired A | 22,500 | $0.00 | $0 | 22,500 | Direct |
| 03 Aug, 2026 | Jeffrey D Fick | Chief Legal Officer | Acquired A | 7,500 | $0.00 | $0 | 7,500 | Direct |
| 31 Jul, 2026 | Debbie Sharell Roberts | Director | Acquired J | 408 | $61.24 | $25.00K | 30,402 | Indirect |
| 31 Jul, 2026 | Paul Bennett Medini | Director | Acquired J | 471 | $61.24 | $28.83K | 9,932 | Indirect |
| 27 May, 2026 | Craig W Kliethermes | Chief Executive Officer | Acquired P | 5,000 | $52.00 | $260.00K | 153,990 | Direct |
| 01 Jun, 2026 | Clark C Kellogg | Director | Acquired P | 3,000 | $50.90 | $152.70K | 4,502 | Direct |
| 28 May, 2026 | David B. Duclos | Director | Acquired P | 2,500 | $51.99 | $129.98K | 9,780 | Direct |
| 27 May, 2026 | Craig W Kliethermes | Chief Executive Officer | Acquired P | 2,000 | $52.00 | $104.00K | 150,990 | Direct |
| 27 May, 2026 | Jennifer L Klobnak | Chief Operating Officer | Acquired P | 2,000 | $52.72 | $105.44K | 104,318 | Direct |
| 21 May, 2026 | Craig W Kliethermes | Chief Executive Officer | Acquired P | 5,000 | $52.00 | $260.00K | 148,990 | Direct |
| 19 May, 2026 | Jennifer L Klobnak | Chief Operating Officer | Acquired P | 2,000 | $53.42 | $106.84K | 102,318 | Direct |
| 13 May, 2026 | Jordan W Graham | Director | Acquired M | 1,681 | $0.00 | $0 | 118,108 | Indirect |
| 13 May, 2026 | Clark C Kellogg | Director | Acquired M | 1,681 | $0.00 | $0 | 1,681 | Indirect |
| 13 May, 2026 | David B. Duclos | Director | Acquired M | 2,353 | $0.00 | $0 | 18,388 | Indirect |
| 13 May, 2026 | Michael J Stone | Director | Acquired M | 1,681 | $0.00 | $0 | 433,248 | Direct |
| 13 May, 2026 | Robert P Jr Restrepo | Director | Acquired M | 1,681 | $0.00 | $0 | 26,433 | Direct |
| 13 May, 2026 | Paul Bennett Medini | Director | Acquired M | 1,681 | $0.00 | $0 | 9,028 | Indirect |