Outright: Windsor Walks Off Festus for the JCAA Title

Four years ago, Windsor lost a Jefferson County Activities Association softball title in the bottom of the seventh inning, when Hillsboro scored three times in its last at-bat to take the 2022 league crown. Thursday in Imperial was the same inning with the other ending. Two outs, a 1-2 count, Festus 2, Windsor 2, and Faith Willtrout, per the GameChanger scorebook, singled to center field. The run it scored made the Owls 3-2 winners and, at 6-0 in league play, JCAA large-schools champions, alone. A year ago the same two teams met on the last day of league play with the same title at stake, and ended up sharing it.

What was on the table

The JCAA settles its softball title on the regular season and awards it in two divisions by enrollment, large schools and small. The large-schools race had been cut to two teams by Monday, when Windsor won 9-4 at Hillsboro. That left Windsor and Festus both 5-0 in conference play with one league game apiece: this one. The winner would finish 6-0 and alone. The loser would finish 5-1, which is exactly where both ended up last October. They tied at the top after Windsor won 6-3 at Festus on Oct. 9, 2025, a week before the Owls beat the Tigers again, 11-5, in the district semifinal. By MSHSAA's results, no league game remains for either team, which makes this title Windsor's outright.

Festus arrived at 20-6 on an eight-game winning streak. In the circle was Ava Oberle, the two-time JCAA Player of the Year and this week's Athlete of the Week in the Leader, Jefferson County's weekly newspaper, after a five-inning perfect game against Jefferson on Oct. 1. As of that Oct. 6 story she was hitting .518 with nine pitching wins. Windsor arrived at 16-10 on five straight wins since a 2-1 loss to Notre Dame of Cape Girardeau on Sept. 26, and with a record that reads worse than the team: 1-5 in one-run games, all five losses inside a 23-day stretch in September.

A family matter

Windsor coach Wayne Montgomery, in his 16th season, is the younger brother of Festus coach Jeff Montgomery, in his 28th, a Missouri High School Fastpitch Coaches Association Hall of Fame selection on his brother's nomination. Each has a daughter on his roster, Windsor junior second baseman Ella Montgomery and Festus senior Olivia Montgomery, so Thursday was a game between first cousins as much as between rivals. "It took me six years before I beat him in softball," Wayne told the Leader in January 2025. "The past few years we've been back and forth."

Two swings for Festus

Through six innings the game had three runs, and Festus seniors drove in two of them. Carlie Isbell doubled home a run in the third. Ty Schenck, Windsor's all-state center fielder, answered in the bottom of the inning with an RBI single to left, 1-1. Then nothing, until Aubrey Doyle hit a solo home run to center in the top of the sixth. Festus 2, Windsor 1, and Oberle needed six more outs for the title. Festus got five.

The seventh

Gracie Willtrout tied it. The junior catcher, all-state last fall, the one whose diving catch on a foul ball ended the 2025 district final, singled to center with a runner on to make it 2-2. Then, with two outs and the count 1-2, Faith Willtrout singled to center, per the scorebook, and the run that scored was the championship. The Windsor dugout emptied onto the infield.

A team that had spent September losing the close ones had just won the closest one of all, in its last at-bat, against the league's two-time Player of the Year.

Holland's night

Anna Holland threw all seven innings for Windsor: four hits, two runs, two walks, three strikeouts. Two swings beat her and nothing else did. The senior, all-state as a junior, threw complete games in all three district wins and the state quarterfinal last October, and did it again with the league on the line. Oberle's line in the loss: 6 2/3 innings, eight hits, three runs, six strikeouts, one walk. Peyton Stemmler, a sophomore outfielder, had two of Windsor's eight hits.

The title, in context

Festus won the 2024 crown outright at 6-0, the year it ended Hillsboro's five-year run with a 3-0 win in Hillsboro that was also Jeff Montgomery's 400th career win. Jeff Montgomery had six JCAA titles to his name when the Hall of Fame vote came in, and Festus shared another last fall, which until Thursday was the only JCAA softball title Windsor had claimed since Hillsboro's run began in 2019. Windsor has now beaten Festus three straight times; the Tigers' last win in the series was a 10-0 shutout in Imperial on Oct. 10, 2024. This is the program that reached the state final four for the first time last October. As a No. 4 seed, it swept De Soto, Festus and Hillsboro for its first district title since 2003 and finished fourth in Class 4. Our August preview said Windsor had raised the bar for the county. The bar now has a conference title on it that nobody has to split.

What's next

Windsor, 17-10 after Thursday, hosts Sullivan on Monday at 4:30 p.m. Festus, 20-7, plays Fox the same afternoon. Then the Class 4 District 1 tournament, Oct. 14-20 at Windsor: Cor Jesu is the No. 1 seed, Windsor No. 2, Festus No. 3, Hillsboro No. 4. Windsor opens Thursday, Oct. 15, at 4 p.m. against Central of Cape Girardeau; Festus follows at 6:15 p.m. against Farmington. If the seeds hold, these two could meet again in the semifinals, the round where Windsor ended Festus's season a year ago. The Class 4 state quarterfinals are Oct. 24, and the Class 4 final four is Oct. 29-30 at Killian Softball Complex in Springfield.

For the record: play-by-play is from the GameChanger scorebook and the Live Stream STL broadcast; no outlet had published a box score by Friday. Conference and overall records are compiled from MSHSAA results.

Live Stream STL carried Windsor's last three conference games, including Thursday's, which is up on the site to watch back. The 2026 Jefferson County softball preview has the rest of the county picture. Athlete development, as always, by M4P — Movement 4 Power.

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