Before diving into today’s post, please take the time to fill out the School Board’s Survey, which is now live through the end of July – dgsurveys.com/r/WhitefishBay2026. While the prior survey was physically mailed to households in the district, this edition of the survey is online. Paper copies can be obtained by emailing districtnews@wfbschools.com
The Whitefish Bay School Board is once again weighing whether to renovate or build a new middle school, likely at the Armory Park site. It’s the most ambitious version of an idea the community has wrestled with for nearly four decades. The building at 1144 E. Henry Clay St., which originally opened in 1919, was too small from the day it reopened as a school in 1989, and the district has spent the better part of the past forty years patching, expanding, studying, voting, and debating about what to do next.
Here’s how we got here.
1988: Converting Henry Clay into the Middle School
The recent middle school debate didn’t begin with a new building. It began with an old one.
In early 1988, Superintendent LeRoy Rieck proposed converting the Henry Clay Community Education Center — the former Henry Clay School that had been repurposed as a community hub in 1980 — into a middle school for grades 6 through 8. Cumberland and Richards would become K-5 schools. The estimated savings: $250,000 a year (almost $750,000 in 2026 dollars) from consolidating specialty teachers who then traveled between buildings.
The plan immediately stirred controversy. Senior citizens, as well as others, had come to rely on Henry Clay for meetings, lunch programs, social activities and rec department and MATC classes. They showed up to meetings in force to oppose it. Lydell Elementary (at the time holding K-2nd grade) parents circulated a 539-signature petition. Some residents questioned whether the building was even large enough to support a real middle school program.
The school board voted unanimously to approve the plan anyway at a June 1988 meeting before an audience of more than 500, with a cheer erupting in the high school auditorium when the result was announced. The vote among the crowd had been 315 to 216 — far from unanimous, noted Board President Carolyn Wilson, who acknowledged that “clearly, there are people who are not happy with the decision.”
Financing was cobbled together to convert Henry Clay and Lydell for their future uses: $1 million from the district’s operating reserves and a $750,000 loan from the State Trust Fund. Total renovation cost was estimated at $1.75 million (roughly $5 million in 2026 dollars), with a new gymnasium addition at Henry Clay accounting for $640,000 of that total.
The gym addition was pilloried by neighbors who compared the bare brick wall to the Berlin Wall.
The Armory, still standing and in use at the time, was located on the same block as the middle school and allowed the school district to use a 10-foot strip of its property for a new parking lot at the time in exchange for the district paying for its construction. Even in 1989, the Armory and the middle school were neighbors making arrangements with one another.
1989: Opens. 1991: Already Crowded.
The Whitefish Bay Middle School opened in August 1989 with approximately 500 students (this past school year that number was 608). Within two years, it was straining at the seams.
By March 1991, the school board approved $100,000 to carve three additional classrooms out of the old gymnasium stage and basement space. Some board members were already uncomfortable. “These classrooms won’t have windows,” said board member Ruth Derse. “No one will want to be in them.”
The school’s enrollment was growing, and the building was simply not built for what was being asked of it.
1994: The First Failed Referendum
By early 1994, the Middle School Study Commission, a group of parents, teachers, and elected officials, had studied 31 options and recommended a $4.4 million expansion ($10 million in 2026 dollars). Enrollment at the time was 581, against a designed capacity of 600, with projections showing 700-plus students by 1999. Some classrooms already had 31 students, violating the district’s own policy of 23 to 25.
The board also weighed a more dramatic option: building a brand new school, either at Cahill Square or on the old Lydell School site. That would cost roughly $10.3 million. The board rejected the new school idea in February 1994 and voted 4-3 to put the $4.37 million renovation on the May ballot.
The board was bitterly divided. Three dissenters said they would neither campaign for it nor against it. The Whitefish Bay Taxpayers Association ran a vigorous opposition campaign, arguing the plan was too expensive, the building was too old to justify the investment, and finally (this will sound familiar!) that the Armory property — which the Wisconsin National Guard was expected to vacate in the coming years — should be considered as a site for a new school before the district committed to patching the old one.
Voters rejected the referendum in May 1994 by a vote of 1,975 to 1,366. 33% of eligible voters voted in that referendum versus the 70% of eligible Villagers who voted in April 2026 (Way to go today’s voters!)
In the aftermath, the board floated alternatives: moving eighth graders to the high school (dismissed as educationally damaging and logistically impossible — the high school lacked adequate science and computer labs, and the eighth graders would need different schedules and start times), or physically swapping the middle school and high school buildings entirely (administrators called this workable only as a temporary measure). The middle school concept itself was briefly questioned.
1995: Second Try Barely Passes
On its second attempt, the district came back with a refined plan the following April. The new proposal called for a two-story, 26,000-square-foot addition to the east end of the middle school building, adding 28 rooms including 13 classrooms and six science labs, widening hallways, upgrading electrical, plumbing, and mechanical systems, relocating the school office closer to the entrance, enlarging the cafeteria, and expanding the media center. Total cost: $4.9 million ($10.8 million in 2026 dollars), with $890,000 coming from district reserves and $3.9 million in borrowing, if approved by voters on April 4, 1995.
The Taxpayers Association again campaigned against it, accusing the board of “theatrics and emotions” and calling the renovation “shortsighted” given that the Armory property might soon be available. “Explain a school board which knowingly rushes into an irrevocable multi-million dollar project without possessing all the facts regarding the loss of substantial future state aids,” their Vote No statement read.
Advocates for Education, a citizens group that had formed after the May 1994 defeat, pushed back hard. “A new school, perhaps at a cost of $12 million or $15 million, is not economically feasible at the armory or any other site,” their Vote Yes statement said. “There will be no new school or third referendum attempt a year from now if the community votes ‘no’ Tuesday. There will simply be an unmet educational need in our community.”
Voters approved the referendum on April 4, 1995 — by 2,980 to 2,898. Fewer than 100 votes separated the two sides.
2009 Referendum
The 2009 referendum included two questions that ultimately passed. The first asked for $9 million for maintenance and renovation funds to be used across all school facilities in the district. The second question asked for $13.6 million to mainly fund additions to the High School, Richards and Cumberland. The Middle School received a new gym floor as well as a relocation of the orchestra room from the basement from the 2009 referendum.
Now: A New School, The Same Debate
Thirty years later, the building at 1144 E. Henry Clay St. is again at the center of a community debate. The district’s Facilities Advisory Committee spent years studying all of the district’s buildings and concluded that the middle school, now 107 years old, with additions dating from the 1930s, 1950s, and 1980s, as well as the 1990s expansion voters barely approved, has reached the end of its useful life for modern education. The April 2026 referendum asked voters to approve a package that included a new middle school at Armory Park, at a cost of $67.7 million. It failed, 52% to 48%.
The board is now gathering community feedback through focus groups (June 16 and July 14) and a community survey before deciding in August whether to put a revised question on the November 2026 ballot.
The parallels to the 1990s are striking. Then as now, the community was divided between those who wanted to renovate and expand what exists and those who argued that investing in a century-old building is throwing good money after bad. Then as now, cost was a central objection. And then as now, the Armory property was identified by some as the right place to build something new and by others as a complicating factor that the board was moving too fast to properly consider.
There are also differences. The 1994-95 debate was primarily about whether to expand a school that was overcrowded with students. Today’s debate is about whether to replace a building that is aging out of functionality — mechanically, structurally, and educationally — while enrollment stays steady. The dollar figures have grown by an order of magnitude. And the community now has thirty more years of experience with what the current building can and cannot do.
The board has been careful to say that the needs identified in April haven’t changed. What they’re trying to figure out is how to build the community trust that would make acting on those needs possible.
In 1988, a board member quoted a philosopher’s advice to the school board: “If you wait until you have all the information to make the decision, it’s clearly too late to make the decision.” The board moved forward at that time. Whether Whitefish Bay is ready to move forward now, and on what terms, is the question the focus groups and community surveys are designed to help answer.
As mentioned in the above images, this post references a number of articles from the Mimi Bird Collection at the WFB Library in addition to other articles pulled from the Journal Sentinel’s archives.
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