Sr. Judith Schaefer – 2023 St. Joseph Award recipient

Sr. Judith Schaefer - 2023 St. Joseph Award recipient

Leadership, service to others, and making personal connections within Cotter and throughout the Winona community were hallmarks of Sr. Judith Schaefer’s presidency at Cotter Schools.

The St. Joseph award, in honor of the patron saint of Cotter High School, is given to individuals who have contributed substantial amounts of their time, talents, and resources to Cotter over a number of years.

As President of Cotter Schools for ten years from 2012-2021, Sr. Judy’s contributions went above and beyond these criteria.  In that time the school saw substantial additions and renovations to buildings and the campus, a dramatic increase in enrollment, the unification of the K-12 school system, and the vision of a clear plan for the future growth and development of Cotter Schools.


Sr. Judy addresses the Cotter student body at the St. Joseph and Alumni Awards assembly

A lifetime learner

Sr. Judy, who is a Sinsinawa Dominican Sister, earned her BA in Education from Northern Illinois, University, she earned a Master degree in Pastoral Studies from Loyola University, a Master of Divinity degree from the Aquinas Institute of Theology, and a Ph.D. in Theology from Marquette University.

She’s the real deal in both representing and living Roman Catholic faith

— Greg Sobolewski

Prior to becoming President of Cotter, Sr. Judy has taught at every imaginable level of education from kindergarten to graduate school. She was a high school religion teacher in Iowa, served on the religion faculty at Edgewood College in Madison, WI, and was a Professor of Theology at St. Mary’s University in Winona, then served as University Dean for University Affairs at St. Mary’s, among other stops.

“Sr. Judy was an energetic, engaging teacher, who collaborated with her students.,” said former St. Mary’s University colleague Greg Sobolewski. “Sr. Judy’s subsequent service at SMU and Cotter has magnified these traits of knowing and inspiring people in their day-to-day living. She’s the real deal in both representing and living Roman Catholic faith.”

While she was at St. Mary’s, Sr. Judy was serving as an academic adviser to then Cotter parent and Board of Directors member Annmarie DeMarais, who was completing a graduate program in Pastoral Studies at the university.  Annmarie was involved with the presidential search at Cotter and, over the course of several conversations, inquired as to whether Sr. Judy would consider applying for the position, given her leadership experience in Catholic education.  Sr. Judy eventually considered the proposition, applied for the post and  was hired as Cotter’s president, for what she initially thought would be an interim position.

a new leader rights the ship

Cotter had gone through significant recent turnover in administration, faculty, and staff when Sr. Judy came on board in May, 2012. One of the first challenges for the new President was to develop a culture where people felt safe to share their concerns and try to instill a collaborative process for making decisions.

“When I arrived there was a palpable sense of tension and anxiety in the air with many of the staff and so the first thing I tried to do was just to listen to people and affirm their value to the school,” Sr. Judy said.

Sr. Judy came to Cotter and provided stability at an important time in the school’s history

— Dave Forney

“As a leader who jumped into the Cotter Family mid year, she made the transition so smooth for all of us. I appreciate her candor, her humor and her incredible giving to Cotter and the wider community, ” Cotter faculty member Mary Hansel-Parlin said. “I still miss the Sinsinawa caramel rolls at Christmas!”

A task that greeted her the first year was leading Cotter through an accreditation process. While never a pleasant process for schools, it did give Sr. Judy a chance to take inventory of what the schools strengths and weaknesses  and gave her a starting point on a journey to positive growth for the school.

“Sr. Judy came to Cotter and provided stability at an important time in the school’s history. Sr. Judy is people oriented and has always shown concern and care to our students, staff and community. She is a great example of Christ’s love and a friend to so many,” Cotter principal Dave Forney said.

Sr. Judy, in her doctoral robes, presents Hannah Graf (Class of ’21) with an award

one system, one campus

One goal that many with the Cotter and Winona Catholic education community, including benefactors and school leaders, was to unify the elementary, junior high and high school under one administrative umbrella. Part of this plan  was also to bring the all the students onto one campus. Sr. Judy was instrumental in bringing this “one system, one campus” vision to fruition.

“As a member of a religious order and President of Cotter Schools, Sr. Judy was instrumental in working with the Diocese of Winona-Rochester and the parishes to navigate the path to becoming a unified system. She worked skilfully and comfortably with all the stakeholders in bringing pre-K -12 Catholic education in Winona into one entity.”” DeMarais said. 


Sr. Judy outside of Loretto Hall with seniors Paige Peplinski Adamary Rosas-Garcia, and Ben Herber in 2018

renovation and new construction

An enduring piece of Sr. Judy’s legacy at Cotter is the number of major projects that were undertaken during her presidency. “I enjoyed working with others to create a vision and then doing the planning and detailed work to bring that vision to life,” Sr. Judy said.

a performance space returns

One of the gems of the campus is the St. Cecilia Theater. A beautiful concert space that was originally designed for piano and vocal performance,  the snug 400 seat theater had amazing acoustics, but was in dire need of major repairs, starting with replacing a plaster ceiling that was constructed in a fashion no longer used in new builds. Thanks to the generous support of the Slaggie Family Foundation, the enormous task of replacing the ceiling, repainting the entire theater, installing new seats, and putting in a state of the art sound system was undertaken. Sr. Judy was involved in every step of the process, down to choosing  the color scheme for the paint and what type of chairs would go in the theater.

“Sr. Judy cared so much about the project she was personally polishing the brass rails on the balcony on the day of the ribbon cutting event, she really put her heart into each project,” Annmarie said.

The theater is back to hosting all sorts of Cotter events, including band and choir concerts, school plays, award ceremonies and assemblies. It is also used  for community events. This year the Frozen River Film Festival held a screening there during the week of the Festival.

The Hurry Back Productions concert series, under the direction of Mike Slaggie, is held in the theater has become a fixture on the Winona social scene and continues to grow in both number of shows and attendance.

St. Joseph Hall

One of the final building projects of Sr. Judy’s tenure was overseeing the design and construction of St. Joseph Hall (formerly the Roger Bacon building) and the Residence Center as part of the Slaggie Family Complex, which now house grades 9-12 classrooms, cafeteria, and a 72 student capacity student residence facility.


The exterior of St. Joseph Hall, which houses the majority of Cotter High School classrooms. Sr. Judy was instrumental in guiding the buildings design and the move to the new facility

One of people Sr. Judy worked closely with on these projects was Cotter’s head of maintenance, John Wineski. “Sr. Judy was a very kind and caring President. She would go out of her way to help me get things done if I could show it would be beneficial for Cotter.  We. of course, had disagreements during projects, but by the end of the day, things were always good between us. She would always tell me ‘You’re the best, and I have you on speed dial,”  Wineski said.

Main Square Montessori

When Fastenal founder and Cotter benefactor Bob Kierlin sought to add an early childhood Montessori school in Winona under Cotter’s governance, Sr. Judy was up for the challenge and served as the schools first president and CEO.

“In the spring of 2018, Mr. Kierlin approached Sr. Judith Schaefer, president of Cotter Schools, and asked if they would partner with HEF [Hiawatha Education Foundation] to build and open a Montessori School as a part of the Main Square development project. And the dream took off,”  Main Square Montessori school director Jacque Paulsen said in a 2019 Winona Post article.

In 2019 Main Square Montessori opened its doors in downtown Winona

Centennial Gymnasium

The Construction and dedication of the Centennial gymnasium in the John Nett Rec. Center, dedicated in 2015, began in 2011, 100 years after Cotter was founded in 1911. The addition of the gym and renovation of the lobby and first floor of the John Nett Rec. building have been a boon to Cotter’s athletic programs, giving the school a much needed second gym.  The lobby is used throughout the day and after school by students. 

The lobby of the John Nett Rec. Center, renovation was completed early in Sr. Judy’s tenure

A new tradition

One tradition that Sr. Judy brought to Cotter, perhaps borrowed the LaSallian Brothers at St. Mary’s University, was the celebration of Founder’s Day  This annual event commemorates groups and individuals who were integral to the history of the school.  In 2014, there were parish priests, a former prinicpal, Franciscan Sisters, and Christian Brothers present for the occasion. In 2015 the members of the Hiawatha Education Foundation were honored. A number of Christian Brothers were able to attend the event held in the junior high gym in the John Nett Rec. center in 2016.  In 2018 Bishop Cotter and Bishop Heffron were honored as students did a cemetery walk to learn about their stories.

Sr. Judy with a group of Christian Brothers on Founder’s day

keeping faith in the forefront of student life

In addition to the work Sr. Judy oversaw with administrative governance and major projects, she also took a number of steps to enrich the faith lives of the Cotter students and staff. She started an all-school Thursday morning prayer assembly.  Students meet in the St. Cecilia theatre for 15 minutes to start the day with a reflection on a piece of scripture and a sort of thought for the day. Sr. Judy led these assemblies and they have continued since her departure and now led by faculty and students. The assemblies always close with a prayer Sr. Judy wrote and the students and staff have committed to memory.

The Cotter morning prayer

Sr. Judy also created the Cotter Book of Prayer, which is a book on the first floor of the school where students can write in special prayer intentions so the community can pray for people and issues in their lives.

She also created the “Cotter Cares” fund, to help with incidental expenses for students who are facing financial difficulties.

Sr. Judy conducted exit interviews with graduating seniors to wish them well and find out what they truly appreciated in their time at Cotter and where they saw room for improvement.

community partner and increased enrollment

“I always tried to work with our partners in education in Winona, whether it was with Scott Olson at Winona State, or the superintendent’s at 861, or with my friends from St. Mary’s,” Sr. Judy said. 

In 2014 Sr. Judy worked with one of Cotter’s most generous benefactors to secure a tuition assistance grant that reduced tuition by nearly 50% for local families. Since the gift was received, pre-K through 12th grade enrollment has increased by 45 %.

a helper in times of need

In addition to fulfilling her administrative duties, Sr. Judy always brought a caring touch to the school.

“Sr. Judy excelled at the ministry of presence. She was an exceptional listener and always willing to lend an ear and a helping hand to those in need, whether it was someone who dropped into her office with a problem or going out onto the football field with the trainer to check on an injured player,” DeMarais said.

A large house fire broke out at house of Vila St. near the intersection of Vila and 5th St on the morning of Friday, January 19, 2018. The smoke from the fire was so dense and toxic that the Winona Fire Dept. had Cotter shut school down and have an early release for the safety of the students. An elderly couple lived in the house and upon hearing this Sr. Judy set up a safe space for them on the first floor of the St. Teresa building so they had a place to go and be comforted and cared for amidst the chaos.

There was a Cotter student from China who needed to return home due to some personal struggles, and Sr, Judy flew all the way to China to assure the students safe arrival home. She stayed near the airport and flew back to Minnesota the next day.

challenges, rewards, and moving on.

The were of course constant obstacles and challenges to face as president.  These included dealing with students who weren’t doing there best or getting in trouble, meeting with parents in these situations, navigating all the complex decisions that arose at eh outset of the pandemic, and securing funding for school operations and special projects. 

She valued diversity of opinions, and she was always willing to listen to others.  As her employee and co-worker, it was a wonderful example to witness

— Mary Eileen Fitch

On the other she loved to lift up and share in students’ successes. She loved watching Ramblers work hard not just in school, but coming to sporting events and cheering Cotter on. She also loved working with the Cotter Board, benefactors, community partners and Cotter families, to try to forge a path to a better educational and community experience for all Ramblers and Winonans.

“Sister Judy had a tremendous impact on students, families, and employees with whom she worked every day. She exemplified care and concern for each and every person she encountered, always desiring what was best for each individual,” DeMarais said. “She felt called to serve as President of Cotter, and when it was time to pass it on, she helped recruit Mary Eileen Fitch to work at Cotter.

“Sr. Judy was an intelligent, well-informed, and compassionate leader for Cotter Schools.  She valued diversity of opinions, and she was always willing to listen to others.  As her employee and co-worker, it was a wonderful example to witness.  She was a gifted counselor, and she lived her faith by truly seeing the face of God in each student, parent, staff and community member she encountered,” Cotter President Mary Eileen Fitch said.

In her decade long tenure at Cotter, Sr. Judith Schaefer left an indelible mark on the campus, organizational structure, and lives of the students and staff at Cotter Schools. She is a most deserving recipient of the St. Joseph Award.