Maryland's Winningest Active High School Football Coaches Entering 2026

With DeMatha's Bill McGregor taking a leave of absence and River Hill's Brian Van Deusen retiring, two of Maryland's three winningest active high school football coaches from the 2025 season will not be on the sidelines in 2026. That leaves Linganore's Rick Conner as the state's winningest active head coach.

Conner owns a 243-77 career record, comfortably ahead of the rest of Maryland's active coaches. La Plata's Danny Hayes ranks second with 203 wins, followed by Milford Mill Academy's Reggie White and Westlake's DaLawn Parrish, who are tied for third with 198 victories. Patuxent's Steve Crounse rounds out the active Top 5 with 186 wins.

Conner Starts His 41st Year Coaching in Frederick County

Conner made his head-coaching debut at Brunswick in 1987 and spent three seasons there with moderate success before stepping back into an assistant's role. He spent the next 12 seasons working under two of Maryland’s all-time winningest and most legendary coaches: Ben Wright at Thomas Johnson (1990-94) and Dave Carruthers at Urbana (1995-2001).

Conner's impact as a defensive innovator was evident early. Thomas Johnson went 20-3 in his final two seasons under Wright. Urbana compiled a 60-5 record during Conner's tenure on Carruthers' staff, including four consecutive state championships in Conner's final four years with the program, from 1998 through 2001.

In 2002, Conner took over as head coach at Linganore, allowing him to build a dynasty of his own. The Lancers reached the state championship game in his first season and won the title in 2003, meaning Conner had coached in six consecutive state championship games.

Over his 24-year run at Linganore, Conner has guided the Lancers to 14 seasons with at least 10 victories, four state championships, and eight state runner-up finishes. His teams qualified for the playoffs in 21 of 23 possible seasons, as there was no 2020 postseason due to COVID-19.

Conner currently ranks tied for 10th in all-time wins in Maryland and enters the season five victories shy of ninth-place Tim Ambrose's 248.

Dan Paro Reclaims the Private School Throne

With McGregor stepping aside at DeMatha, Dan Paro once again becomes Maryland's winningest active private-school head coach, a distinction he previously held after McGregor first stepped down in 2010.

Paro was later passed by Bob Milloy during Milloy's run at Good Counsel, regained the distinction when Milloy stepped down in 2016 and relinquished it again when McGregor returned to DeMatha in 2019. Now it's back with Paro, whose 185 victories since 1997 are especially impressive considering Georgetown Prep does not have a postseason. Only once during his tenure has Prep played more than 10 games in a season.

Reggie White, DaLawn Parrish Closing In on 200 Wins

Reggie White, a former NFL player-turned-high school coach, and DaLawn Parrish, a high school star who played at Wake Forest, are knocking on the door of 200 career wins. Both enter the season at 198 career victories.

Steve Crounse, currently at Patuxent, also has a mathematical shot at 200 this season, but he would need 14 victories to get there. That would require an unusually long postseason run for a team that could receive a first-round playoff bye with a strong regular season.

John Kelly Stands Out

While Quince Orchard's John Kelly ranks 10th in total victories, his 135-11 career record gives him by far the highest winning percentage among the coaches in the Top 10.

Maryland's Active Career Coaching Win Leaders Entering 2026

1. Rick Conner, Linganore, 243-77

2. Danny Hayes, La Plata, 203-94

T-3. Reggie White, Milford Mill Academy, 198-82

T-3. DaLawn Parrish, Westlake, 198-60

5. Steve Crounse, Patuxent, 186-71

6. Dan Paro, Georgetown Prep, 185-91

7. James Monroe, Lake Clifton, 152-155

8. Donald Davis, Mount St. Joseph, 144-87*

9. Mike Nesmith, Paint Branch, 143-59

10. John Kelly, Quince Orchard, 135-11

11. Tommy Green, Eleanor Roosevelt, 134-54

12. Rob Harris, Broadneck, 125-38

13. Rich Holzer, Loyola Blakefield, 123-65

14. Vince Ahearn, Thomas Johnson, 122-161

15. Patrick Nixon, Mergenthaler Vo-Tech, 119-32

16. Bryon Sofinowski, Queen Anne’s, 118-64

17. Kurt Stein, Oakdale, 112-54

18. Eric Woodson, Atholton, 112-100

*Davis has 156 career victories overall, including two full seasons at Sidwell Friends (D.C.). The rankings above count Maryland victories only.

Note: Current Oxon Hill coach Craig Jefferies has 198 career victories, but the majority came during his tenure at Dunbar (D.C.), where his teams won eight D.C. city championships.

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