Kentucky had 4 of the Top 50:


5. (5) Philip Haywood — 471
Current school: Belfry (Ky.)
Record: 471-154-0
Years: 48 (1975)
State championships: 7
Last year: 6-6

14. (15) Dudley Hilton — 418
Current school: Bell County (Pineville, Ky.)
Record: 418-132-0
Years: 45 (1974)
State championships: 3
Last year: 10-3

32. (38) Larry French — 356
Current school: Middlesboro (Ky.)
Record: 356-172-0
Years: 45 (1978)
State championships: 2
Last year: 7-4

38. (46) Kevin Wallace — 346
Current school: St. Xavier (Louisville, Ky.)
Record: 346-116-0
Years: 37 (1984)
State championships: 6
Last year: 10-2

Coaches of that breed will be few and far between going forward. The longevity is incredible. 

Coach Haywood averages 9.81 wins per season.
Coach Hilton averages 9.29 wins per season.
Coach French averages 7.91 wins per season.
Coach Wallace averages 9.35 wins per season.

The overall leader, Coach JT Curtis of John Curtis Christian (the Louisiana team Male was originally scheduled to play in 2021) averages 11.39 wins per season.

The #2 man, Robert Hyland from St. Mary's Springs (WI) averages 9.67 wins per season.

The #3 coach, Jim Roth from Southern Columbia (PA) averages 12.41 wins per season.

Just now, Colonels_Wear_Blue said:

Coach Haywood averages 9.81 wins per season.
Coach Hilton averages 9.29 wins per season.
Coach French averages 7.91 wins per season.
Coach Wallace averages 9.35 wins per season.

The overall leader, Coach JT Curtis of John Curtis Christian (the Louisiana team Male was originally scheduled to play in 2021) averages 11.39 wins per season.

The #2 man, Robert Hyland from St. Mary's Springs (WI) averages 9.67 wins per season.

The #3 coach, Jim Roth from Southern Columbia (PA) averages 12.41 wins per season.

I did some extrapolating to compare a few of the other guys in the state, Brandon Smith, Eddie Eviston, and Justin Haddix:

Brandon Smith: 99 Wins
Current School: South Warren (KY)
Record: 99-18-0
Years: 9 (2014)
State Championships: 2
Last year: 6-6
Average Wins Per Season: 11.00
On Pace To Crack Current Top 50 In Wins: 2043 (30th Season/Age 56)
On Pace To Overtake Current Leader In Wins: 2069 (56th Season/Age 82)

Eddie Eviston: 121 Wins
Current School: Covington Catholic (KY)
Record: 121-30-0
Years: 11 (2010)
State Championships: 4
Last Year: 9-3
Average Wins Per Season: 11.00
On Pace To Crack Current Top 50 In Wins: 2041 (30th Season/Age 61)
On Pace To Overtake Current Leader In Wins: 2067 (56th Season/Age 87)

Justin Haddix: 129 Wins
Current School: Boyle County (KY)
Record: 129-40-0
Years: 13 (2010)
State Championships: 3
Last Year: 13-2
Average Wins Per Season: 9.92
On Pace To Crack Current Top 50 In Wins: 2042 (33rd Season/Age 58)
On Pace To Overtake Current Leader In Wins: 2071 (62nd Season/Age 87)