KENOSHA, Wis. — Kenosha Unified School District Superintendent Jeffrey Weiss (D) will receive well over a quarter-million dollars in salary and direct compensation for the 2026-27 school year, including a $240,261 salary and another $21,000 taxpayer-funded tax-sheltered annuity, for $261,261 before taxpayers spend another dime on his Wisconsin Retirement System pension contribution, health, dental, vision, disability and life insurance, retiree health and dental benefits, 25 paid vacation days, 12 paid sick days, paid holidays, technology and other reimbursable expenses. And those are hardly the only perks taxpayers have provided Weiss (D) since he arrived. His contracts have included a $500-per-month vehicle allowance, or $6,000 a year, a $10,000 annual tax-sheltered annuity that was later increased to $15,000 and now $21,000, and even an $8,550 transition stipend when he came to Kenosha. In other words, Weiss (D) has theoretically already become a millionaire off the backs of KUSD taxpayers. Based on the salaries and fringe benefits spelled out in his contracts, a reasonable estimate is that taxpayers have spent approximately $1.1 million compensating him since he took over the district in October 2022.

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That contrast is difficult to ignore. Enrollment goes down … financial reserves go down … public confidence goes down … schools close … staffing goes down … the district’s financial outlook gets worse … taxpayers reject a massive referendum. But somehow, through all of it, Jeff Weiss (D)’s pay keeps going up.

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When Weiss (D) was hired in 2022, his original contract provided for a $220,000 annual salary, prorated for the remainder of the 2022-23 school year because he began Oct. 1, 2022. It also gave him a $10,000 taxpayer-funded tax-sheltered annuity, a $500-per-month vehicle allowance and an $8,550 transition stipend. In December 2023, the School Board amended his contract, increasing his 2023-24 salary to $228,800 and increasing the annual taxpayer contribution to his tax-sheltered annuity from $10,000 to $15,000.

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The next contract continued the upward march. For 2024-25, Weiss (D) was guaranteed at least $228,800, with increases tied to compensation increases given to other administrators. His taxpayer-funded annuity remained $15,000 per year, the $500 monthly vehicle allowance remained, the district continued paying its share of his Wisconsin Retirement System pension, and taxpayers continued providing his insurance and other benefits.

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Now Weiss (D)’s newest contract provides a $240,261 salary for 2026-27 and pumps the taxpayer-funded tax-sheltered annuity up again, this time to $21,000 annually. It also provides taxpayer-funded retirement contributions, insurance, retiree health and dental insurance under certain conditions, paid holidays, 25 vacation days and 12 sick days. In other words, Weiss has gone from a $220,000 stated annual salary when he arrived to more than $240,000 today, while his separate taxpayer-funded annuity has more than doubled from $10,000 to $21,000.

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So while KUSD keeps telling taxpayers there is never enough money, there always seems to be enough money for the superintendent.

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The District Is Running Out Of Money

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KUSD itself has acknowledged enormous budget problems. The district has been dealing with multimillion-dollar deficits, drawing on reserves, reducing staffing and making cuts while warning that its financial problems are not going away. That is what makes the steady upward march of Weiss (D)’s compensation so difficult to defend.

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Think about it. The organization Weiss (D) is paid nearly a quarter-million dollars a year just in salary to lead has been staring at eight-figure budget holes, closing schools, reducing employees, cutting expenditures and relying on reserves to keep itself afloat. Yet the man ultimately responsible for leading that organization is rewarded with an increasingly valuable compensation package and additional contractual job security. In most organizations, sustained financial deterioration eventually produces accountability at the top. At KUSD, it apparently produces another contract.

KUSD has already made enormous reductions. The district has closed seven schools and merged two others, reduced teachers, support staff and administrators, cut discretionary spending and slashed spending in other areas. Student enrollment has fallen dramatically in recent years. Enrollment down … schools closed … teachers reduced … support staff reduced … administrators reduced … spending reduced … reserves under pressure. Jeff Weiss (D)’s compensation? Up.

That is the upside-down world of Kenosha Unified School District.

Voters Already Said No

The public has also delivered KUSD a rather clear performance review. In February 2025, the district asked voters for $23 million more every year for five years, a breathtaking $115 million referendum. Voters rejected it. Whatever explanation district administrators prefer for that defeat, one fact cannot reasonably be disputed: a majority of the voters who showed up were not willing to hand KUSD another $115 million.

One might think such a result would lead district leadership to seriously reconsider how it spends money and how much confidence the public has in the people making those spending decisions. Instead, KUSD is already moving toward the possibility of another referendum. The district is again spending money and administrative resources studying how to go back to taxpayers after taxpayers already gave them an answer.

So the pattern continues. KUSD has less money … fewer students … fewer schools … fewer employees … shrinking reserves … and a rejected referendum behind it. Yet taxpayers are again being prepared for the possibility that the answer is to give the district more money. Meanwhile, the superintendent who has been at the helm through much of this receives a higher salary, a richer annuity and another contract.

What About The Kids?

Ultimately, a school district exists for one reason: to educate children. It does not exist to preserve administrative salaries. It does not exist to protect an organizational chart. It does not exist to employ consultants, launch referendum campaigns or guarantee that the people at the top are financially insulated from the consequences being felt everywhere else in the district.

To be fair, KUSD’s most recent state report card improved, and that should be acknowledged. The district remained in the state’s “Meets Expectations” category and there were improvements in several measures. Pretending otherwise would weaken rather than strengthen the argument.

But an improved report-card year does not erase the broader reality confronting the district. KUSD remains in serious financial trouble. Enrollment has fallen dramatically. Seven schools have been closed. Staffing and spending have been cut. Reserves are under pressure. District leaders are again contemplating asking taxpayers for more money after voters rejected the last enormous request. Those are the conditions under which the School Board has nevertheless decided that the superintendent deserves continued increases in compensation and contractual security.

Academic performance should also matter enormously when the School Board decides how lavishly to compensate its superintendent. Taxpayers ought to be able to ask a simple question: are Kenosha children receiving educational results that justify continuing to increase the compensation and job security of the person at the very top?

Accountability Apparently Stops Before The Superintendent’s Office

In most workplaces, executives are rewarded for results. Grow the organization, improve the product, stabilize the finances and strengthen confidence in leadership, and the person running the organization has a strong argument for a raise. When important indicators move sharply in the wrong direction, people naturally begin asking whether leadership should share in the consequences.

At KUSD, taxpayers appear to have stumbled upon a completely different compensation model. Enrollment down … more money for Weiss. Seven schools closed … more money for Weiss. Eight-figure deficits … more money for Weiss. Reserves being depleted … more money for Weiss. A $115 million referendum rejected … another contract. Another possible referendum … another year of job security.

The School Board approved Weiss (D)’s newest contract Aug. 25, 2026. It begins July 1, 2026, runs through June 30, 2028 and can be extended further. Most remarkably, the contract specifically says Weiss’s salary in subsequent contract years “shall not be less than” the $240,261 he receives for 2026-27.

That clause may be the perfect metaphor for KUSD right now. Almost everything else is allowed to go down. Jeff Weiss (D)’s pay is contractually protected from doing the same.

Taxpayers Are Being Asked To Sacrifice. Where Is His Sacrifice?

KUSD’s message to the public is increasingly about sacrifice. Employees may have to sacrifice … teachers may have to sacrifice … students may have to sacrifice … parents may have to sacrifice … taxpayers may again be asked to sacrifice by sending KUSD more money. Yet at the very top of the organization, taxpayers are paying Weiss (D) $240,261 in salary, another $21,000 into a tax-sheltered annuity, retirement contributions, extensive insurance benefits, paid vacation, sick leave, holidays and still more benefits.

This is not an argument that the superintendent of a large Wisconsin school district should be poorly paid. The job is important, and its compensation should reflect that. A superintendent who produces strong academic outcomes, stabilizes district finances, attracts families, maintains enrollment and restores public confidence can make a persuasive argument for substantial compensation. But compensation should have some relationship to results, particularly when the same taxpayers funding that compensation are repeatedly being told the district itself does not have enough money.

And consider the cumulative picture. Weiss (D) has been sitting in the superintendent’s chair for less than four years, and a reasonable estimate based on the salary and fringe benefits laid out in his contracts puts his taxpayer-funded compensation at around $1.1 million already. By the end of his newest contract, taxpayers could easily have spent well over $1.5 million on Weiss between salary, annuity contributions, retirement, insurance and other contractual benefits. That is a tremendous public investment in one administrator. Taxpayers have every right to ask what kind of return they are receiving on it.

KUSD faces enormous financial problems … enrollment has fallen … schools have closed … staffing has been reduced … spending has been cut … voters rejected a $115 million referendum … and district leadership is again contemplating asking taxpayers for more money. Through all of it, Jeff Weiss (D) keeps getting raises, richer benefits and longer contracts.

There is a very simple lesson being taught inside Kenosha Unified School District: when KUSD’s numbers go down, Jeff Weiss (D)’s pay goes up.

That may be the one KUSD performance metric taxpayers can count on.