Daily Journal Boys’ Athletes of the Year: Menlo’s Jack Freehill and Chuck Wynn

But Wynn knew the Menlo football team needed Freehill, as the Knights were fielding a sparse roster with the program readying to play its second season in the stacked Peninsula Athletic League Bay Division.

“Iron sharpens iron,” Wynn said. “So, we became hungry and had a really strong brotherhood. I think we had the grit and mentality. We wanted it more than other teams. We definitely weren’t the biggest, and we were the smallest in numbers, but we just outworked teams.”

They sure did.

Once Freehill returned, the young gridiron Knights took off, starting the season on a seven-game winning streak. With Freehill at quarterback, and Wynn playing in all three phases as a running back, linebacker and punter, Menlo went on to qualify for the Central Coast Section Division II playoffs, advancing to the semifinals with a benchmark 17-7 win over the King’s Academy in the postseason opener.

“We always have that smaller roster size but this year we had higher expectations,” Freehill said. “Even though we were playing these schools that had like triple our roster size, the main goal was just to win.”

Freehill went on to be named PAL Bay Division Offensive Player of the Year, while Wynn earned first-team All-PAL Bay honors as a running back. But it was just the start of the two pairing for an amazing 2025-26 school year that has earned both recent Menlo graduates Daily Journal Boys’ Athletes of the Year honors.

During the winter, Wynn joined the Menlo boys’ soccer team and led the Knights in scoring en route to another CCS playoff run. While he played predominantly off the bench, Wynn earned second-team All-West Bay Athletic League honors after sharing the team lead with senior Declan Setter, scoring 10 goals on the year. Goal No. 10 for Wynn came in the CCS Division III playoff opener, an equalizer in stoppage time to tie it 1-1. Menlo went on to win it in overtime on Setter’s 10th goal of the season.

The kicker is, the win extended Menlo soccer’s season into the CCS semifinals, keeping Wynn from joining the baseball team for their season opener four days later.

“And all the baseball kids were there, and they were pissed,” Wynn said.

Menlo baseball opened its season Feb. 25, the same day Menlo soccer was eliminated with a 2-0 loss to Christopher-Gilroy. So, while Wynn missed the first two baseball games of the season, it wasn’t long before he reunited with Freehill on the diamond to help navigate — surprise, surprise — another Menlo postseason run.

While Wynn was admittedly banged up at the beginning of soccer season, he was refreshed after playing 12 games on the pitch. It’s a good thing, too, as he was not only a middle-of-the-order presence in the Menlo batting order, but also the team’s starting catcher.

“He’s kind of just an animal,” Freehill said. “So, he’s not really complaining about catching for seven innings. ... He just plays. He doesn’t really complain.”

While Freehill didn’t play a winter sport for Menlo, he still had his nose to the grindstone. Outside of the fall season on the gridiron, Freehill spends the rest of the calendar year honing his baseball skills, with a natural left-handed swing along with a rangy presence at shortstop.

Hitting in the No. 2 spot for a Menlo squad that celebrated a Central Coast Section championship three-peat, Freehill enjoyed a career year at the plate, slashing .379/.531/.600, while he and Wynn earned first-team All-PAL Bay Division honors.

“Through high school ... [Freehill] has never had an offseason for baseball; like year-round it’s just grind, grind, grind,” Wynn said. “So, he’s been so consistent with his work ethic and is dedicated to getting better. He always has just wanted to be the best on the field.”

Yet, while Freehill already had already signed to play NCAA Division I baseball at Columbia, Wynn entered the baseball season still shopping for a school.

“The recruiting process wasn’t really the prettiest with me,” Wynn said.

A Redwood City native, who counts baseball among his first loves, Wynn had an offer on the table to play football from the NCAA Division III program at Chapman University. Wynn held off on committing, though, because he preferred to field baseball offers.

That’s when Wynn caught lighting in a bottle, getting off to a fast start to his senior baseball season that proved the best power show in the PAL. The right-handed hitter entered the season having hit two regulation home runs in his entire life, both coming in the same game as a junior in a May 8 blowout of Woodside. Less than five weeks into his senior season, Wynn had hit seven home runs, including a three-homer game April 4 against Aptos.

Wynn went on to win the PAL Bay Division home run crown with 10 on the season.

“He came into baseball and, he’s just a freak athlete and it showed,” Freehill said. “Just coming in and doing what he did was crazy.”

The power production helped Wynn achieve his recruiting goal, as Chapman baseball made him an offer halfway through the spring. He will be attending the campus in Orange, just five miles from Disneyland, as a two-sport athlete.

“Chapman is also like one of the more competitive DIII schools,” Wynn said. “Obviously, I wanted the opportunity to play two sports, and Chapman is competitive in both, and that’s rare to have a school that’s competitive in both.”

Freehill and Wynn are not the first Menlo football players to be honored among the Daily Journal’s year-end awards. Senior lineman Palmer Riley earned Daily Journal Football Player of the Year honors at the end of the fall season. But Freehill and Wynn were in the conversation.

Wynn rushed for racked up over 900 total yards for the season straight season, rushing for 832 yards on 130 carries with five touchdowns, while making 12 catches for 110 yards and two more scores. Freehill, after throwing for five touchdowns in Menlo’s season opener against Hozho Academy-New Mexico, gained 2,252 total yards, passing for 1,563 yards and 22 TDs, while also totaling 96 carries for 676 yards and 11 TDs, along with 13 more yards on his second career reception.

Menlo football finished its PAL Bay Division slate in disappointing fashion, falling 28-0 to eventual league champ Los Gatos in the penultimate week of the Bay season. It was a costly loss as the abbreviated roster finally caused Menlo to stumble, with injuries and illnesses forcing the Knights to forfeit their Oct. 31 Bay Division finale against Wilcox.

Freehill wouldn’t return until the playoffs, but Wynn fronted Menlo’s regular-season finale, non-league rivalry win 21-6 over Sacred Heart Prep. The rivalry Valpo Bowl also glimpsed the future, with junior Caleb Cohen starting under center in place of Freehill. It’s a future that will see Menlo remain in the Bay Division for a third straight season next year, a road that Freehill and Wynn certainly helped pave.

“We definitely wanted to move up [in 2024], compete against some better teams and be in a higher division for playoffs,” Freehill said. “We like the competition. Even though we lost against Gatos twice, we enjoyed getting to play against them and we had a lot of fun doing that.”