Milwaukee County’s highest-paid employee received $250,000 in student loan repayment assistance over the past two years, while County Executive David Crowley’s administration allocated millions in opioid settlement funds to the Medical Examiner’s Office, including money designated for student loan forgiveness.
According to a Milwaukee Journal Sentinel report published Monday, Dr. Joseph Calderaro, an assistant medical examiner hired in July 2023, was Milwaukee County’s highest-paid employee in both 2024 and 2025.
As part of his employment agreement, the county agreed to pay $250,000 toward Calderaro’s student loans, including $150,000 in 2024 and another $100,000 in 2025. Calderaro received more than $415,000 in total compensation in 2024, making him the county’s highest-paid employee by more than $50,000.
County Deputy Comptroller Jim Moon told the Journal Sentinel that Calderaro was the only county employee to receive more than $100,000 in educational supplements over the past decade.
The county defended the arrangement as a recruitment and retention incentive, citing a nationwide shortage of forensic pathologists and longstanding staffing challenges within the Medical Examiner’s Office.
Millions in Opioid Settlement Funds Directed to Medical Examiner’s Office
A September investigative report from the Institute for Reforming Government (IRG) found that Milwaukee County allocated approximately $2.29 million in opioid settlement funds to the Medical Examiner’s Office, including funding designated for student loan forgiveness for a forensic pathologist.
The report also identified approximately $192,000 for a portable body cooler and $19,000 for five autopsy carts, raising questions about whether equipment used for general medical examiner operations should qualify for funding intended to address the opioid epidemic.
While the Journal Sentinel documented Calderaro’s $250,000 in student loan assistance, the available reporting does not establish precisely how much of those payments came directly from opioid settlement funds rather than other county resources.
The settlement money comes from nationwide lawsuits against opioid manufacturers, distributors, and pharmacies accused of fueling America’s opioid epidemic. Wisconsin is expected to receive more than $874 million through 2038, with 70% distributed to local governments and 30% going to the state.
Although the settlement payments come from the companies involved in the litigation, the lawsuits were pursued by publicly funded government offices, including the Wisconsin Department of Justice, whose operations are supported by taxpayers.
Under Wisconsin law, the money must be spent on approved purposes related to addressing the opioid crisis, including prevention, treatment, and recovery services. However, IRG’s investigation found that no state agency is specifically tasked with directly monitoring and auditing how counties spend the funds, leaving local governments with considerable discretion over expenditures.
Crowley’s Budget Also Raises Medical Examiner Fees
The spending on student loan forgiveness comes as Crowley’s proposed 2027 county budget calls for a series of fee increases within the very same Medical Examiner’s Office.
As the Heartland Post previously reported, Crowley’s latest budget would increase the cost of a death certificate from $168 to $172, cremation permits from $393 to $402, and body transportation fees from $168 to $172. Fees for autopsies and external examinations performed for other counties would also increase by $300 per case.
The proposed increases, which critics have characterized as “death taxes,” come as Milwaukee County faces a projected $50 million budget shortfall.
Drug Kits for Illegals, Syringes, and Other Opioid Settlement Expenditures
Student loan forgiveness is not the only Milwaukee County expenditure drawing scrutiny.
As the Heartland Post previously reported, Crowley’s administration has used opioid settlement funds to support its Harm Reduction MKE initiative, which provides free drug-use supplies through vending machines and home delivery.
The program distributes supplies including syringes, fentanyl test strips, naloxone, and safer-use kits containing equipment used to inject drugs. Crowley has acknowledged that Milwaukee County does not verify immigration status when providing health and human services, meaning these programs are available regardless of immigration status.
IRG’s investigation identified $200,000 for syringe and test-strip services and another $200,000 for safer smoking or injecting kits. The organization also highlighted more than $1 million designated for overdose reduction efforts in Black and Brown communities and $200,000 for the Benedict Center to provide services to women involved in street-based sex work who are at risk of drug overdoses.
Milwaukee County maintains that its harm-reduction initiatives help prevent overdose deaths and reduce the spread of infectious diseases, while critics question whether the county’s spending priorities reflect the intended purpose of the opioid settlements.
The expenditures also leave an important question unanswered: How much of Calderaro’s $250,000 in student loan assistance was paid from opioid settlement funds, and what justification did county officials provide for using money recovered from the opioid industry to finance employee loan forgiveness?
