Based on data from the past 90 days ending February 19, 2026, Winmark's three largest insider shareholders are TenPercentOwner Ronald G Olson (146.34K shares), Chair And Ceo Brett D Heffes (114.40K shares), Chief Financial Officer Anthony D Ishaug (66.48K shares).
| Holder | Position | Shares | Report Date |
|---|---|---|---|
| Ronald G Olson | 146,335 | 26 Nov, 2024 | |
| Brett D Heffes | Chair And Ceo | 114,400 | 28 Aug, 2025 |
| Anthony D Ishaug | Chief Financial Officer | 66,483 | 07 Nov, 2025 |
| Renae M. Gaudette | Chief Operating Officer | 18,860 | 24 Oct, 2025 |
| Leah A Goff | Vp Of Human Resources | 11,575 | 14 Mar, 2022 |
| Paul C Reyelts | 5,333 | 10 Mar, 2023 | |
| Mark L Wilson | 3,788 | 21 Apr, 2023 | |
| Jenele C Grassle | 2,500 | 21 Nov, 2025 | |
| Kirk A Mackenzie | 1,000 | 03 Nov, 2021 | |
| Percy C Jr Tomlinson | 800 | 04 Nov, 2025 | |
| Lawrence A Barbetta | 649 | 18 Sep, 2025 | |
| Gina Decaro Sprenger | 250 | 13 Aug, 2025 |
* Please note that the shares above only reflect shares from the fund portfolio and the institutional portfolio. Shares from the personal portfolio are excluded from this Institutional Ownership Page. See these insiders' latest transactions here on Insider Page.
| Transaction Date | Insider Name | Security Class | Transaction Type | Shares Traded | Price | Shares Remaining | Ownership | Code |
|---|---|---|---|---|---|---|---|---|
| 21 Nov, 2025 | Jenele C Grassle | Common Stock | D | 2,400 | $420.87 | 2,500 | D | S |
| 19 Nov, 2025 | Jenele C Grassle | Common Stock | A | 800 | $125.50 | 4,100 | D | M |
| 19 Nov, 2025 | Jenele C Grassle | Common Stock | A | 800 | $98.25 | 3,300 | D | M |
| 19 Nov, 2025 | Jenele C Grassle | Common Stock | A | 800 | $122.50 | 4,900 | D | M |
| 07 Nov, 2025 | Anthony D Ishaug | Common Stock | A | 510 | $195.82 | 66,483 | D | M |
| 07 Nov, 2025 | Anthony D Ishaug | Common Stock | A | 2,490 | $98.25 | 65,973 | D | M |
| 04 Nov, 2025 | Percy C Jr Tomlinson | Common Stock | A | 600 | $197.80 | 800 | D | M |
| 24 Oct, 2025 | Renae M. Gaudette | Common Stock | D | 1,100 | $415.43 | 18,860 | D | S |
| 24 Oct, 2025 | Renae M. Gaudette | Common Stock | D | 100 | $435.62 | 19,960 | D | S |
| 22 Oct, 2025 | Renae M. Gaudette | Common Stock | A | 2,500 | $90.99 | 20,060 | D | M |
| 17 Sep, 2025 | Lawrence A Barbetta | - | - | 1,285 | D | |||
| 17 Sep, 2025 | Lawrence A Barbetta | Common Stock | D | 216 | $505.33 | 1,285 | D | S |
| 17 Sep, 2025 | Lawrence A Barbetta | Common Stock | D | 636 | $504.91 | 649 | D | S |
| 17 Sep, 2025 | Lawrence A Barbetta | - | - | 649 | D | |||
| 27 Aug, 2025 | Brett D Heffes | Common Stock | D | 1,186 | $454.03 | 116,200 | D | S |
| 27 Aug, 2025 | Brett D Heffes | Common Stock | A | 2,868 | $164.84 | 117,981 | D | M |
| 27 Aug, 2025 | Brett D Heffes | - | - | 115,113 | D | |||
| 27 Aug, 2025 | Brett D Heffes | Common Stock | D | 1,630 | $452.72 | 114,570 | D | S |
| 27 Aug, 2025 | Brett D Heffes | - | - | 117,386 | D | |||
| 27 Aug, 2025 | Brett D Heffes | - | - | 117,981 | D |