It was feast or famine for Simon Kenton in 2025.
In six wins, they had an average margin of victory of 18 points. In six losses, they had an average margin of defeat of 33.3 points. Even at 6-6, the Pioneers enter 2026 with momentum, garnering their first playoff victory since 2022 with a first round win over Oldham County before losing to eventual state champion Trinity in the second round.
It’s Joe Wynn’s second season as the leader of the program, and his past history with a program in their second season bodes will for the Pioneers. In his second season at Newport, they went 8-4, a two win improvement from the first year and at Mason County in Wynn’s second season they went 13-1, a four-win improvement and one of the best seasons in Royals history with a trip to the state semifinals.
“It starts in the offseason, kids know us and what to expect,” Wynn said. “Numbers always jump in the second year, credit to kids recruiting and staff recruiting. You get more comfortable with things and knowing what you have and putting the puzzle together. It’s just having some more pieces to the puzzle and continue to put it all together.”
Here’s five things to know about the Pioneers as they head into the 2026 season:
Momentum
While a single playoff win in a season isn’t the standard in Independence, it is certainly a move in the right direction. This was a program from 2008-19 that won 25 playoff games and reached a state championship game in 2008 and the semifinals in 2015.
Since 2020, Simon Kenton had just one playoff win heading into the 2025 season. That came in 2022 against Marshall County.
Now the sights are set even higher as they try and chase their first district title since 2022. There’s still a lot of work to be done and a lot of the heavy lifting will be done by a talented junior class.
“We had 60 guys in the weight room often this offseason,” Wynn said. “They didn’t miss a day and they were ready to grind and get after it. You can feel the buzz in the community. The youth practices on our campus, will play games on our campus. There’s a ton of football around here. We’re trying to get back to the 2008-2019 levels.”
How does the defense improve?
Allowing 30.9 points per game last season is certainly an area for improvement. Wynn has his right-hand man back on the defensive side as Derek Webster will take over the defense. Webster was with Wynn at Newport and Mason County before being the head coach at Western Hills in Cincinnati the past two seasons.
“I learned a valuable lesson last year where I couldn’t gameplan both the offense and the defense,” Wynn said. “Derek will call the defense.”
While the opponents scoreboard was being lit up, some of those numbers are a bit miscontrued. Turnovers didn’t help the cause. The Pioneers turned the ball over 27 times. That’s putting the defense in a bad spot.
“We’re in a game and then things go haywire,” Wynn said. “It’s pretty simple. We can’t turn the ball over. When we did last year, things started to spiral.”
Some continuity will help too. While Webster is in his first year with the team, guys that may have never played defense before at the high school level were thrust into those roles. Things will look a little different scheme-wise under Webster.
“Kids have played both sides now for a second year,” Wynn said. “The main lesson from year one to year two is respond together, mold together and not break a little bit. Last year we’d go into the second or third quarter and we have a turnover and things started to spiral.”
Webb brings quite the physique
At 6-foot-5, 215 pounds, you can’t miss Grant Webb on the sidelines. You’ll also wonder if he puts on the basketball shoes in “The Joe” in the winter for the Pioneers.
He took over the reins in his sophomore season coming off a season where he threw for 1,810 yards and 11 touchdowns. It came with some growing pains as he threw 20 interceptions and completed just under 50% of his passes.
A year of experience and growth (literally and figuratively) should create quite the improvement for his junior season.
“He got so much better,” Wynn said. “He was more dynamic last year as the season went on. We’ll run him more this year and he can really throw it. He can get it down the field 65-70 yards. We just need to limit mistakes, he needs to trust his guys and execute the offense.”
Who he throws to on Friday nights is still to be determined, but Wynn is optimistic with the depth at the receiver positions. Of the 121 receptions that were made last season, 104 of them came from seniors, 57 for 1,124 yards and seven touchdowns from one of the most decorated Pioneers to put a jersey on in Grayson Harris, who continued his career at Georgetown College.
Forest Hughes is the returning leading receiver with 11 catches for 295 yards and five touchdowns. His twin brother Samuel will also look to take the step up. From there, Wynn will hope to turn to Michael Newborn also out wide. Moise Smith will try and provide the home run hitting in the backfield. Peyton Testerman will also get touches in the backfield.
“We’ll look to spread it around and have multiple guys score it,” Wynn said. “That’s when the offense is at its best when the defense has to prepare for multiple guys.”
Junior? Junior!
Every name mentioned so far is headed into their junior year. It was a unique makeup of the team last year where the majority of the production came from seniors and sophomores.
That doesn’t mean Wynn won’t be turning to a lot of seniors this year. Some guys he’s looking to step up are Kai Brewer at running back, Anthony Sparkman, Cohen Endicott and Easton Sakraida along the line.
Health will be a big key for Jack Giordano, he’ll be a big part of the defensive backfield and also at receiver. Injuries have limited him the past two seasons.
Kyle King is another key part of the defense at linebacker and will play tight end.
Beat Ryle on three
When Simon Kenton breaks away from a station, huddle or practice, they end it with “Beat Ryle on three, state champs on six.”
Ryle has set the standard in recent years and the Pioneers are looking to take it back. After late game failures in 2023 and back-to-back blowouts by the Raiders, Simon Kenton has set the target squarely on the Raiders. The first goal is a district title and it runs through the black and orange in Union.
“We’re building to beat them,” Wynn said. “Win a district title, win a regional title and then who knows what happens. But in order for us to get to that point, we have to take things one week at a time.”
The Pioneers sister district for the playoffs this year is Male, Bullitt East, Southern and Fern Creek. That means no Trinity, St. Xavier or DuPont Manual until at least the region championship game. If Simon Kenton can handle their business in the district, that also means they most likely wouldn’t see Male in the first two rounds either.
We’re previewing all 22 NKY football teams from July 27-August 17. Check out five things to know about each team below:
