The Deep Post: The 2026 Kennedy Award preseason rankings

Welcome back to The Deep Post, a weekly column covering the happenings from around the area, though the introduction is a little off.

This is this week’s second edition of the Deep Post and it goes beyond the scope of the area, taking a look at the statewide Kennedy Award race.

Since 2022 I’ve dedicated The Deep Post that follows the quarterfinal round to the Kennedy Award race as it’s become a deeply impactful award in the southern part of the state. Since my first season in 2017, the area has produced five of the last nine winners.

Last year I did something different, conducting a straw poll where I asked several voters to anonymously rank their top three candidates heading into the final week of voting. This year I’ve elected to do the same but for a preseason ranking. 

I asked six fellow voters to rank their top five candidates in order coming into the season and they graciously obliged in helping with this project. I added my ballot as well, which I’ll disclose later. 

My goal was to get participation from voters from all corners of the state who have their finger on the pulse of high school football and take their ballots seriously. 

I sent the following list of players to my peers as a starting point but told them they could add whoever they wanted. The list was meant to be guide. Only two players who weren’t on the list (Lucas Lambert of Logan and David Robinson of Herbert Hoover) received votes.

Dakota Dalton, Chapmanville (QB)

Peyton Grigsby, Herbert Hoover (QB)

Gavin Williams, Bridgeport (RB)

Maddox Twigg, Morgantown (QB/DB)

Max Simpson, Bluefield (QB)

Brian Dick, Martinsburg (QB)

Colton Robertson, Pendleton County (QB)

Anthony Smith, Fairmont Senior (QB)

Boston Todd, Martinsburg (WR)

Brock Green, Independence (QB)

Hayden George, University (WR)

Jaden Black, George Washington (RB)

Here’s how the voting shook out

A few observations:

• Morgantown’s Maddox Twigg is the overwhelming preseason favorite. He appeared on all seven ballots with five first place votes. He was second on the other two ballots. That’s not a surprise. He’s a two-way star with DI pedigree and became only the first quarterback since 2006 to beat Martinsburg in the title game. For reference the Bulldogs were 11-0 in title games during that period. 
• Bluefield’s Max Simpson benefitted from a similar boost. He appeared on six of the seven ballots after breaking four Class AA title game passing records in the Beavers’ title game loss to Frankfort. His game-tying drive in the final minute that ended in a 40-yard touchdown pass and subsequent 2-point conversion on an end-zone fade left a statewide impression. He may lose ground playing one way.
• Boston Todd was Martinsburg’s top contender for this award a year ago but from talking with people around the state who saw QB Brian Dick this summer, he appears to have taken the lead. That seems to be reflected here but it’s close.
• I’d be stunned if the award isn’t a quarterback award for the next two years and these early ranking reflect that. That said, George Washington running back Jaden Black and Bridgeport running back Gavin Williams are strong contenders. I’d give an edge to Williams though. I’m not sure GW will be a semifinalist and it’s hard to win the award if you can’t make it to Thanksgiving. I trust that Williams and his team will have a better shot of making a deep playoff run in a stacked classification.
• I was a little surprised Herbert Hoover QB Peyton Grigsby appeared on just one ballot but I feel like that’s more indicative of the depth of the field. He was a 3,000-yard passer a year ago and their roster is loaded with talented skill players. There’s the argument they may canibalize each other but Grigsby would still be the statistical beneficiary. The addition of all-state running back David Robinson may cut into those numbers but Robinson is dynamic as a pass catcher. When Grigsby played with a first team all-state back last year in Blake Fisher he was still wildly productive. Class AAA is the most competitive class and Hoover should be near the top all season. Couple that with a schedule that features opportunities for signature wins against Fairmont Senior, Parkersburg, South Charleston, Princeton and Huntington and there should be room for a Hoover player to rise through the rankings when I revisit this topic around midseason.
• I believe this will be the closest Kennedy race since Bluefield’s Mookie Collier barely edged the reigning winner Jeremy Dillon in 2017. That puts an extra emphasis on winning every game. That’s where the field has the opportunity to catch Twigg. Morgantown has a lot of holes to fill and a challenging schedule that features a home head-to-head with Martinsburg. If Morgantown rolls through its in-state schedule and returns to Charleston, Twigg should run away with the award. 
• I’m not overly familiar with Huntington’s players but I was a little surprised there wasn’t at least one Highlander submitted.

Here’s my straw ballot:

1. Maddox Twigg
2. Max Simpson
3. Brian Dick
4. Jaden Black
5. Peyton Grigsby

Nobody has ever won the Kennedy Award in the preseason but given our process of voting features no discussion amongst voters in the way it does every other award, the watchlist is informative. 

A historic 2028 quarterback class, the best that’s ever come through the state, should dominate this award for the next two years but that doesn’t rule out a dark horse winner. I’d argue that from 2021-23 the eventual winners (Atticus Goodson, Judah Price and Dom Collins) weren’t on anybody’s radar in August. That changed by November.

We’ll see if 2026 gives us another contender when we revisit the topic.

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Tyler Jackson

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