Power and Age: Big Brother Over‑40 Champions of Competitions

In the chaos and excitement of Big Brother, age can be thought of as a disadvantage, but when seasoned veterans step up, they often secure major strategic wins. Here’s a casual look at all notable American Big Brother players who were over 40 at the time—and won competitions—detailing their age, their victories, and the season they dominated.

Evel “Dick†Donato – Age 44 (Season 8, Winner)

“Evel Dick†Donato entered Big Brother 8 at 44 years old and made history as the oldest winner ever of the U.S. series. During that run, he claimed multiple competition victories, most notably a critical Head of Household win and at least one Power of Veto, using his experience and direct style to steer the endgame. Evel Donato’s combination of bold gameplay and comp strength helped him win the season outright, defeating his daughter Daniele in the Final Two by a 5–2 vote.

Jerry MacDonald – Age 75 (Season 10)

Oldest HouseGuest

At 75, Jerry MacDonald stands as the oldest HouseGuest in Big Brother history. He wasn’t just a statistic; he competed fiercely. In Season 10, Jerry won Head of Household in Week 1, instantly asserting authority in the house. Impressively, he also won two consecutive Power of Veto competitions in Weeks 4 and 5, a rare feat, especially for someone outside the usual competitive prime. He ultimately finished in third place after 66 game days, cementing his reputation as a strategic elder statesman.

George “Chicken†Boswell (Season 7)

George “Chicken†Boswell (47) in Season 7 All-Stars did win a Power of Veto and later an HOH, but never claimed multiple or final comps.

Gerald “Gerry†Lancaster (Season 3)

Gerry Lancaster (in his 50s during Season 3) did indeed win major competitions: he claimed two Power of Veto wins (Weeks 1 and 6) and also won Head of Household in Week 4. Despite alliances cracking around him, he reached 7th place and even cast the tie-breaker vote in Week 4 eviction.

Diary Room Confessionals

Renny Martyn (Season 10)

Renny Martyn (aged 53 during Season 10) secured exactly one HoH win, in Week 6 (“Diary Room Confessionals†competition). She did not win any Power of Veto and lost in the Final Five.

Cliff Hogg III (Season 21)

Cliff Hogg III (in his 50s during Season 21) returned via the Battle‑Back twist and soon made an impact. He won one PoV in Week 1. Later, he captured one HoH in Week 11. That was his only recorded Veto win, and he finished as a jury member in 5th place.

Jack Owens Jr. (Season 4)

Jack Owens Jr. (retired and in his late 40s/50s during Season 2) won two HoH titles—Week 1 and Week 4—and also captured one PoV in Week 4. He ended the season in 7th place and served on the jury

Kevin Schlehuber and Glenn Garcia

Kevin Schlehuber (Season 19) and Glenn Garcia (Season 18) were both veteran contestants over age 40. Neither won a Head of Household nor any Power of Veto. Kevin did win a Temptation competition during his season, but that does not qualify as a formal PoV or HoH win. And Glenn’s contributions as an “Alter Ego†twist participant didn’t include official competition trophies.

Victory was significant

Dick Donato’s victory was significant because he overcame much younger competitors in a finale that awarded him $500,000. His bold style and aggressive gameplay complemented his comp strength. Jerry MacDonald’s early HoH and Veto sweep in Season 10 showed that even the eldest contestant could dominate physical and endurance-based challenges, at least early in the game.

If there’s one takeaway, it’s that age doesn’t disqualify power moves in Big Brother. Dick and Jerry show that experience, grit, and the ability to perform under pressure can elevate even seasoned competitors.