| 2023-11-30 | OLIVO MARIA | EVP, Strat Dev & Pres Intl | Sale+OE | 7,000 | $179.92 | $1,259,451.90 | -6.3% | → |
| 2023-11-27 | HEYMAN WILLIAM H | Vice Chairman | Sale+OE | 270 | $178.00 | $48,060.00 | -0.1% | → |
| 2023-11-03 | BESSETTE ANDY F | EVP and Chief Admin Officer | Sell | 3,797 | $169.38 | $643,162.44 | -22.6% | → |
| 2023-07-24 | Klein Michael Frederick | EVP & President, Personal Ins. | Sale+OE | 10,000 | $175.05 | $1,750,479.00 | -41.5% | → |
| 2023-05-10 | Klein Michael Frederick | EVP & President, Personal Ins. | Sale+OE | 10,246 | $182.85 | $1,873,435.13 | -23.8% | → |
| 2023-04-25 | BESSETTE ANDY F | EVP and Chief Admin Officer | Sale+OE | 11,572 | $178.14 | $2,061,466.73 | -16.4% | → |
| 2023-04-21 | Frey Daniel S. | EVP & Chief Financial Officer | Sale+OE | 37,316 | $179.08 | $6,682,418.62 | -34.7% | → |
| 2023-02-23 | Klenk Jeffrey P. | EVP & Pres., Bond & Spec. Ins. | Sell | 2,132 | $185.15 | $394,730.21 | -26.0% | → |
| 2023-02-23 | Lefebvre Mojgan M | EVP & Chief Tech & Ops Officer | Sell | 5,375 | $183.49 | $986,230.07 | -100% | → |
| 2023-02-23 | Toczydlowski Gregory C | EVP & President, Business Ins. | Sell | 5,420 | $184.19 | $998,215.74 | -22.7% | → |
| 2023-02-14 | Kurtzman Diane | EVP & Chief HR Officer | Sale+OE | 2,914 | $185.01 | $539,113.31 | -62.7% | → |
| 2023-02-10 | BESSETTE ANDY F | EVP and Chief Admin Officer | Sale+OE | 24,443 | $186.52 | $4,559,174.36 | -63.4% | → |
| 2023-02-09 | Klein Michael Frederick | EVP & President, Personal Ins. | Sale+OE | 20,000 | $185.31 | $3,706,211.10 | -45.4% | → |
| 2023-02-08 | Schnitzer Alan D | Chairman and CEO | Sale+OE | 150,829 | $188.53 | $28,435,685.30 | -17.8% | → |
| 2023-01-26 | HEYMAN WILLIAM H | Vice Chairman | Sale+OE | 9,000 | $191.42 | $1,722,750.10 | -1.8% | → |
| 2022-11-30 | HEYMAN WILLIAM H | Vice Chairman | Sale+OE | 2,000 | $189.88 | $379,750.00 | -0.8% | → |
| 2022-11-30 | Yin Daniel Tei-Hwa | EVP & Co-Chief Invest. Officer | Sale+OE | 5,234 | $188.48 | $986,499.09 | -9.7% | → |
| 2022-11-25 | HEYMAN WILLIAM H | Vice Chairman | Sale+OE | 5,000 | $189.11 | $945,550.00 | -1.9% | → |
| 2022-11-23 | RUSSELL DOUGLAS K | SVP, Corp Contr & Treasurer | Sale+OE | 10,181 | $188.00 | $1,914,028.00 | -36.7% | → |
| 2022-11-23 | Rowland David Donnay | EVP & Co-Chief Invest. Officer | Sale+OE | 7,554 | $187.70 | $1,417,894.11 | -48.0% | → |
| 2022-11-22 | OLIVO MARIA | EVP, Strat Dev & Pres Intl | Sale+OE | 13,000 | $186.29 | $2,421,731.00 | -11.6% | → |
| 2022-11-22 | Klenk Jeffrey P. | EVP & Pres., Bond & Spec. Ins. | Sale+OE | 13,000 | $186.55 | $2,425,194.20 | -68.2% | → |
| 2022-11-22 | HEYMAN WILLIAM H | Vice Chairman | Sale+OE | 7,658 | $187.55 | $1,436,234.84 | -1.5% | → |
| 2022-11-21 | HEYMAN WILLIAM H | Vice Chairman | Sale+OE | 3,342 | $186.05 | $621,783.09 | -0.7% | → |
| 2022-11-15 | BESSETTE ANDY F | EVP and Chief Admin Officer | Sale+OE | 4,420 | $180.74 | $798,870.80 | -23.8% | → |
| 2022-11-08 | HEYMAN WILLIAM H | Vice Chairman | Sale+OE | 1,000 | $185.50 | $185,500.00 | -0.4% | → |
| 2022-11-01 | HEYMAN WILLIAM H | Vice Chairman | Sale+OE | 1,000 | $185.25 | $185,250.00 | -0.4% | → |
| 2022-11-01 | BESSETTE ANDY F | EVP and Chief Admin Officer | Sale+OE | 17,229 | $184.77 | $3,183,342.03 | -55.0% | → |
| 2022-10-31 | Klein Michael Frederick | EVP & President, Personal Ins. | Sale+OE | 10,000 | $183.67 | $1,836,706.00 | -52.3% | → |
| 2022-10-31 | HEYMAN WILLIAM H | Vice Chairman | Sale+OE | 21,000 | $182.74 | $3,837,500.00 | -1.4% | → |
| 2022-10-24 | OLIVO MARIA | EVP, Strat Dev & Pres Intl | Sale+OE | 13,516 | $179.21 | $2,422,180.73 | -12.0% | → |
| 2022-10-24 | HEYMAN WILLIAM H | Vice Chairman | Sale+OE | 1,000 | $180.00 | $180,000.00 | -0.4% | → |
| 2022-08-24 | Lefebvre Mojgan M | EVP & Chief Tech & Ops Officer | Sell | 2,945 | $168.33 | $495,738.03 | -74.3% | → |