Portland High’s Andrew Brewer chases South Portland’s Jaelen Jackson during the 2021 Battle of the Bridge. “It’s a crazy rivalry between Portland and South Portland but it’s also the regional championship,” Brewer says. “So, that together is just a game that we want.” Derek Davis/Staff Photographer

It’s not the only thing that will decide the Class B South regional final, but No. 3 South Portland and No. 1 Portland share a similar goal: slow down the opposing dangerous quarterback.

Red Riots senior Jaelen Jackson has rushed for 1,296 yards and 16 touchdowns this season, throwing for 1,105 yards and another 11 scores. He’s coming off a 180-yard rushing performance with two touchdowns runs and a TD pass in a semifinal win at Massabesic.

Portland is 6-0 since Kennedy Charles became the quarterback midway through the season. Charles, who had no previous experience playing quarterback, has rushed for 1,351 yards and 17 touchdowns. Charles hasn’t thrown often but has completed 24 of 43 passes for five touchdowns. He rushed for 288 yards and four scores in Portland’s semifinal win against Kennebunk.

“There are other great players on the field for both teams and other aspects of football that factor in – field position, turnovers, penalties, injuries,” said South Portland Coach Aaron Filieo. “But I think you definitely have to start with how do you slow down Kennedy and how do you slow down Jaelen?”

Both teams bring 7-3 records to Fitzpatrick Stadium for the game, scheduled for 6 p.m. Friday. The longtime rivals play annually in the Battle of the Bridge (Portland won this year, 20-13) but it’s their first playoff meeting since 2002 (Portland, 21-0) and the first time they’ve played in a regional final since 1995 (South Portland, 28-24).

South Portland has not been in a regional final since 2000, losing to Massabesic in what turned out to be John Wolfgram’s final game as the Red Riots’ coach. Last year Portland, as the unbeaten No. 1 seed, lost to Marshwood, 35-0 in the regional final.


“It’s definitely cool because obviously we played them earlier this year for the Battle of the Bridge and we get another shot to come at them again and try to come out on top this time,” Jackson said.

Portland senior captain Andrew Brewer, who is often Charles’ lead blocker, agrees this game has extra meaning for both teams.

“It’s a crazy rivalry between Portland and South Portland but it’s also the regional championship,” Brewer said. “So, that together is just a game that we want. That gives us a lot more motivation to win the game. Beat the crosstown rival and then hold the plaque as regional champs.”

The Class B North final pits No. 4 Falmouth (7-3) against No. 2 Skowhegan (8-2) at Lewiston High at 7 p.m. Friday. The state championship is Nov. 19 at Fitzpatrick Stadium.

Jackson split time at quarterback for South Portland in 2021. He was also the starting point guard on the Riots’ Class AA championship basketball team last winter. Always a dangerous runner, Jackson has worked hard to improve his passing. He’s completed 75 of 158 passes.

“His field vision, is crazy,” said Nolan Hobbs, South Portland’s tight end and a top receiving target. “He reads defenders and he always throws to the right spot and he’s able to get outside the pocket and throw the ball with accuracy.”


Were it not for a Game 1 injury to Portland starter Sam Esposito, chances are Charles would have continued in his hybrid role of wing back, slot receiver, running back and occasional Wildcat quarterback. But when Portland fell to 1-3, scoring four total touchdowns in consecutive losses to Class C power Leavitt and Class A squads Bonny Eagle and Oxford Hills (with sophomore Louis Thurston replacing Esposito), Bulldogs Coach Jason McLeod knew a change was needed.

It wasn’t that Thurston played poorly, McLeod said. Thurston completed 30 of 56 passes for 415 yards and four touchdowns.

Kennedy Charles has a 6-0 record since becoming Portland High’s quarterback. He has rushed for 1,351 yards and 17 touchdowns, throwing five touchdowns passes. Derek Davis/Staff Photographer

“With Kennedy it was just a point of getting him the ball more,” McLeod said. “We just didn’t think he was touching the ball as much as he should because the few times he did touch the ball previous to (being the quarterback), he was pretty electric.”

Kennedy was not excited about the switch initially.

“I mean at first, I didn’t like the idea but whatever the coaches think is best, I’ll try it out and try to get it to work,” Charles said. “Since I’ve been the starter, we’ve been successful so I haven’t looked back since.”

Brewer said, “We were 1-3 and then after Kennedy got put at quarterback, it was jut a game changer. Everything was different. The atmosphere was different, we felt more comfortable. We had hope basically.”


Charles said his success is a reflection of his blocking.

“The ball might be in my hands but with my line and guys like Andrew leading the way I always feel like I have a helping hand,” Charles said.

He certainly had help in Portland’s regular-season win against South Portland.

The Bulldogs rushed for 334 yards on 45 carries. Charles gained 191 yards, Brewer had 72 and Reegan Buck had another 69 yards. Portland was able to limit Jackson to 51 yards and a touchdown on 13 carries. Jackson completed 8 of 21 passes for 130 yards and a touchdown.

Only subscribers are eligible to post comments. Please subscribe or login first for digital access. Here’s why.

Use the form below to reset your password. When you've submitted your account email, we will send an email with a reset code.