[LeeCoUKFan]

Estill hasn't been in the district long enough to build up a reputation as being a dominant team. They probably will build up that status though in the future, due to the size of their enrollment.
The district tournament goes back much farther than the last 5 years. And Lee County has won only two district titles in the last 20 years. Owsley has won 2 since 2005. From the 1980's through the mid- 2000's Owsley, Wolfe and Powell dominated the district. Owsley has won 34% of the district titles in the last 30 years, and 40% in the last 10 years.
Now, with that being said, the Owls haven't been overpowering in recent years but they did manage to win the district last year. And the next couple of years will be a rebuilding phase. I don't see Owsley as being a factor in the district for the upcoming season and maybe next year too.

Yes, I agree with you. I was just speaking from StrikeOut King's point of view where Estill has only been in the District for 5 years and 3 of the 5 years it has either been Estill or Lee in the District Championship.