Chesterton softball 2026 season preview: Reigning sectional champion Trojans' confidence in having even better season fueled by return of a half dozen powerful hitters

Tom Keegan
Onwardtrojans.com

A year ago at this time the Chesterton softball team went into the season hoping it could build a winning record and win a sectional, neither of which the Trojans had done since 2019.
It’s one thing to believe you can reverse course when it hasn’t happened, another thing entirely when it finally happens.
Well, it has happened.
The Trojans finished last season with a 13-12 record, a sectional title and a respectable performance in a 7-2, season-ending loss to eventual state champion Crown Point.
If those don’t seem like such snazzy numbers, view them through the context of how the season started. The Trojans opened with a 1-5 record and were bludgeoned twice in the regular season by Crown Point by a combined score of 25-3.
So they are launching on the strength of a 12-7 finish to the season and have 21 of 23 home runs back from last season’s lineup.
The Trojans open today at home vs. Hobart in so many ways way ahead of where they were in last season’s road opener vs. the Brickies
“They struggled at the beginning because they had, you know, a tougher year the year before,” second-year head coach Erin Cochran said of her players. “The confidence started to build toward the end of the year and then we won that sectional championship and they were saying we can do this. Then we held Crown Point a lot closer than we did the first two times.”
So the step of building confidence now can be skipped because it’s already there based on last season’s strong finish.
“I think with them having the confidence that they’re going to be better, they’re going to put the time into it,” Cochran said. “They’re going to want to be successful and they’re going to do better.”
Plus, the players are a year stronger, a year more mature.
Having a dominant strikeout pitcher always represents the best path to victory in softball. Chesterton doesn’t have that, but does have a lineup stocked with six players who reached double figures in home runs. Two of them hit in the .400s, three in the .300s.
The six sluggers, listed in order of their batting averages with their averages and home run totals from last season in parentheses: Olivia Milton (.417, 4), Jillienne Pittman (.413, 3), Hannah Florian (.359, four), Lila Miller (.323, 2), Payton Cherep (.322, 5), Lexi Smith (.268, 3).
Pittman, Florian, Miller and Smith are seniors, Milton a junior and Cherep a sophomore.
Cochran, assisted by Wally McCormack and Lexi Benko, explained why she is not worried that the girls will grow home run happy in the wake of hitting so many last year: “No, Wally, he’s big on working on the two-strike approach, to get it into play and if things happen with it with home runs, it falls with it.”
The Trojans’ final home run flew off Miller’s bat in the regional vs. Crown Point, a pitching staff that allowed 10 home runs all season. Miller, the team’s shortstop, certainly wasn’t thinking of hitting a home run when she went to the plate.
“The key for me is making good contact and the ball will take itself out,” Miller said. “You have to let the pitcher supply the power and you just have to meet the ball.”
Florian, who pitches and plays third, takes a similar approach.
“I think it’s normal for people to try to swing for the fences, especially when you are that power hitter, but for me I just have to think about getting hits and then the home runs happen by themselves,” she said.
Pittman, a third baseman, tries to put herself in the right frame of mind each at bat.
“For me, it’s more mental: just think contact. If I’m in a bad mood, then I’m probably not going to hit that ball,” she said. “But if I’m in a better mood and I’m more confident in myself, there is a way better chance of me actually hitting the ball.”
Her response to the question of what puts her in a good mood cracked up her teammates: “Caffiene.”
What else?
“Ibuprofen,” she said. “Cookies.”
More laughter.
A second baseman, Smith said, “For me it’s all a mental game, going up there with a plan, going up there with confidence and just believing that I can hit that ball. And if I get on base, that’s awesome. I’m not thinking about hitting a home run.”
Nothing about the way Cherep, a pitcher/first baseman, played last season revealed her youth and she brings that mature approach with her to the plate.
“I know that my job is just to get a hit and try to move runners, so I don’t think hit it out, I think make contact,” she said.
Milton, the team’s catcher, gets the Trojans going.
“I just think that confidence is key,” she said. “I just have good confidence. I’m the first batter, so I have confidence that if I don’t get on, the hitters behind me will.”
All the girls are convinced this season’s team will win more games than last season’s and enter the season-opener vs. Hobart, which won the 2025 opener 10-7, confident the outcome will be different this time.
“We’ve been working harder through the fall and winter and I think that we’ll be a better team overall,” Cherep said.