As the United States approaches its 250th anniversary, USA TODAY Sports is celebrating the 250 greatest American sports figures of all time. Alongside that national recognition, the USA TODAY Network will spotlight the roots of the country’s sports culture: the high school athletes and sports figures who shaped communities and defined their states and regions.
What’s our rubric for determining the “defining” softball players in Wisconsin history? Some players became local legends on the high school field but didn’t translate that success to college or the pros. Some blossomed late, and their high school days offered only a hint of their eventual greatness. How do we compare or measure those things?
Our aim: Identifying trailblazers and trendsetter whose influence reaches beyond championships and statistics − and whose stories reflect a lasting impact on their state.
Our process is imperfect. Let us know at the bottom who should be on this list.
Anne Cooley-Piesczak, Madison La Follette, (graduated in) 1986
Cooley was arguably the best pitcher of her generation. She pitched all four years she was in high school and guided Madison La Follette to a state semifinal as a junior and a state championship appearance as a senior. Due to the rules at the time, she was allowed to pitch only one inning in the state title game. She then went on to play at DePaul University and won 48 games. She’s being inducted into the Madison Sports Hall of Fame Class of 2026.
McKinzie Freimuth, Kaukauna, 2011
Freimuth was a dominant hitter and showed up on the biggest stage. She was the 2009-10 Gatorade Wisconsin Softball Player of the Year as a junior, when she batted .610. That year, she helped guide Kaukauna to a WIAA Division 1 state championship. Freimuth ended her high school career by being named to the Wisconsin Fastpitch Softball Coaches Association all-state first team all four years. After high school, Freimuth went on to play at Michigan State University.
Gretta Grassel, Boscobel, 2024
Grassel is one of the few four-time Wisconsin Fastpitch Softball Coaches Association all-state first-team players since the 1990s. She was one of the best two-way players: in her senior season, she hit .455 with 25 hits, 25 runs batted in and nine home runs. From the circle, Grassel had a 1.72 earned-run average. Following high school, Grassel took her talents to Mississippi State and played in the 2026 Women’s College World Series.
Kayla Konwent, Westosha Central, 2016
Konwent is one of the greatest and most-feared hitters that the state of Wisconsin ever has seen. She finished her high school career with 50 home runs and 135 walks. The catcher was a three-time Milwaukee Journal Sentinel area player of the year. She was a four-time Wisconsin Fastpitch Softball Coaches Association all-state first-team selection and named Gatorade Wisconsin Softball Player of the Year twice for the 2014-15 and 2015-16 seasons.
Karly Meredith, Kaukauna, 2025
Meredith went on a four-year run during her high school career that may never be repeated. Across four seasons, Meredith won three state titles and is one of two three-time Gatorade Wisconsin Softball Players of the Year. In her senior season, Meredith went undefeated with 28 wins and had 282 strikeouts across 158.1 innings. She finished her career with a 96-1 record, 1,007 strikeouts and a 0.29 ERA. On top of that, Meredith was the Post-Crescent softball player of the year all four years of high school. Her talents went beyond the circle with a .423 batting average, 33 RBI and five home runs as a senior. Following high school, Meredith is playing at the University of Virginia.
Paytn Monticelli, Cedarburg, 2022
Monticelli was a dominant pitcher. She was the 2020-21 and 2021-22 Gatorade Wisconsin Softball Player of the Year. In her junior season, she guided Cedarburg to its first state appearance since 2004 with a 0.69 ERA and 293 strikeouts across 132 innings. As a senior, Monticelli had 306 strikeouts across 131 innings. In 2025, she won a bronze medal with Great Britain at the European Championships, where she pitched 16.1 innings and had 33 strikeouts with a 0.00 ERA. After high school, Monticelli went to the University of Wisconsin before transferring to the University of Oklahoma for two seasons where she won a national championship in 2024. She then transferred to LSU for the 2025-26 season.
Nicole Newman, Madison La Follette, 2014
Newman dominated from the circle in her time in high school, finishing her career with 497 innings pitched and 1,017 strikeouts. She had a career ERA of 0.72 and, as a senior, her ERA was 0.42 with a 22-5 record. Newman was Wisconsin’s Gatorade Player of the Year as a junior and was a three-time first-team all-state selection. After high school, Newman played four years at Drake University and was then drafted in the third round of the 2019 NPF Draft by the Aussie Peppers. In her senior year at Drake, she had five perfect games, which remains an NCAA Division I record.
Brooke Schliewe, Horicon, 2003
Schliewe was a three-time first-team all-state selection and was dominant from the circle. She had three seasons with more than 300 strikeouts, with her highest total coming in 2001 when she had 327. In her career, Schliewe had 1,085 strikeouts. Schliewe guided Horicon to state titles in 2002 and 2003. She holds the Division 3 record for strikeouts in a state tournament game with 19 against Wausaukee in 2002 and doubles in a state tournament game with three in the same game.
Sydney Supple, Oshkosh North, 2019
Supple is one of two Wisconsin high school softball players to be named the Gatorade Player of the Year three times. She earned the award for her play in the 2016-17, 2017-18 and 2018-19 seasons. As a senior, Supple went 29-0, had 298 strikeouts across 167 innings and had a 0.75 ERA. She was also an elite hitter and had a .538 batting average, 50 hits, 12 home runs and 49 RBI as Oshkosh North won its only state title in softball in 2019. In that state championship run, Supple had 36 strikeouts, which is a Division 1 state tournament record. After high school, Supple played for Northwestern University.
Andie Varsho, Marshfield, 2010
Varsho is one of the most accomplished Wisconsin high school athletes as she earned 11 varsity letters and was an all-state athlete in tennis, basketball and softball. She was a first-team all-state selection is softball all four years and finished her high school career with a .574 batting average after hitting .675 as a senior. She played one year of professional softball for the Pennsylvania Rebellion after a career at Purdue where she left as the program’s all-time hits leader.
Who else should be on this list? Some suggestions:
This article originally appeared on Milwaukee Journal Sentinel: Who are Wisconsin’s best-ever high school softball players? Vote here
Reporting by Ben Schultz, Oshkosh Northwestern / Milwaukee Journal Sentinel
USA TODAY Network via Reuters Connect
By Ben Schultz, Oshkosh Northwestern | USA TODAY Network
