What began in 2023 as a fun Q&A with ChatGPT 3.5 has become an annual exercise that keeps up with the accelerating pace of AI development and evolving expectations for how the technology fits into journalism, community identity and the public’s understanding of Milwaukee itself.
The series now functions as an unintentional reference. Each interview captures a distinct moment in the trajectory of modern AI, while also revealing the evolution of the technology and assumptions surrounding its use.
The “ChatGPT” interviews were not conducted as in-person conversations with a physical machine. Each year’s Q&A was generated through a structured digital exchange, in which Milwaukee Independent provided written prompts and AI produced text responses in a controlled environment.
The process reflected a traditional interview format, but each response came from a predictive language model running on a remote server rather than a humanoid device. Evolutionary outcomes reflected the capabilities of successive AI systems, not a change in physical form or presence.
This approach allowed journalists to document the technology’s evolving voice, consistency, and interpretive style over time, while making it clear to readers that the “interview” was an editorial experiment conducted entirely through text.
In 2023, the questions presented by the Milwaukee Independent were largely used to introduce readers to new generative technology. By 2024, the interview tested how AI could interpret cultural and civic life in Milwaukee. In 2025, the format allowed the ChatGPT model to generate its own questions, an editorial decision that reflected how far AI had already advanced in its capabilities.
None of the interviews were intended as predictions. Instead, they asked simple questions each year, based on what you would ask a human.
What inspires you or gives you purpose? What kind of work brings you joy? What gives you hope for the future?
The responses detailed how the tone, structure, and capabilities of mainstream AI have transformed in a short period of time.
The original 2023 interview with ChatGPT 3.5 showed a cautious and constrained model. His responses relied heavily on disclaimers, repeatedly clarifying that he lacked emotion, personal conviction or lived experience.
The answers tended to be literal, sure and general. When asked about Milwaukee, the model draws on familiar tourist landmarks or broad social issues. His language reflected a generation of technology designed to prevent mistakes more than to provide a voice.
In contrast, the 2024 interview using GPT-4.0 demonstrated a shift toward mastery of interpretation. The model provided broader context about Milwaukee’s political history, economic disparities and cultural identity. He responded with metaphors, thematic framing, and structured reasoning that resembled editorial analysis.
Rather than simply naming attractions, it explains how different parts of the city interact with each other and how issues such as segregation or infrastructure shape daily life. The interview questions remained the same to maintain a consistent baseline to 2023. The responses showed a model capable of joining an editorial conversation rather than deflecting it.
The 2025 tranche marked a second major transformation. Using GPT-4.5, Milwaukee Independent allowed the AI to not only answer but also design its own questions. This approach revealed a shift in the technology’s ability to simulate perspective.
The model generated questions about memory, emotional interpretation, and the role of AI in understanding civic identity. His answers relied on techniques of imagery, symbolism and storytelling that would have been inaccessible to earlier versions.
The result was a conversation that feels less like a software demonstration and more like an interview with a conceptual thinker, though still constrained by the limitations of automatically generated text.
Over the course of three years, the “Milwaukee Independent” framed each interview within the same civic context, allowing readers to gauge changes from year to year. The articles also highlighted how quickly AI has become widely used, moving from an online novelty to a structural element of communication tools, work systems and creative workflows.
As AI capabilities advanced, the tone of interviews also reflected a broader cultural shift. In the first part, the model’s responses reinforced the perception that AI was fundamentally a machine with limited usefulness beyond information retrieval.
This prospect is clear because in 2023, the “Milwaukee Independent” treated it as an object of curiosity, using the April Fool’s Day format to soften the public’s skepticism about interacting with an unfamiliar technology that was not supported by its flood of hype.
By 2024, however, AI had become commonplace in Milwaukee workplaces, classrooms, and personal devices, and the interview gauged how people were beginning to use it for interpretation rather than just facts.
The 2025 interview represented something different. AI was no longer a novelty. Instead, the questions and format pointed to a new editorial concern: not what AI can do, but what its presence means for a community shaped by economic inequality, political tensions and questions about local identity.
The model’s self-generated prompts, while not evidence of action, demonstrated the ability to synthesize social themes. He responded with comments about Milwaukee’s cultural structures, its historical contradictions, and its ongoing efforts to define itself across neighborhoods and generations.
This shift reflects broader national trends. As artificial intelligence has become more prevalent in civic decision-making, consumer products, and media production, public attention has shifted away from whether AI is dangerous or useful and toward how it should be integrated responsibly.
The “Milwaukee Independent” interviews captured this shift at the grassroots level, showing how AI has begun to participate — even artificially — in conversations about place, culture and sense of community.
The consistency of Milwaukee as a focal point also provided a stable benchmark for evaluating LLM models. For 2026, ChatGPT 5.1 was asked to review the last three years of interviews. He found that each version of the AI revealed its understanding of context, depth and nuance.
The first template offered brief descriptions of museums, sports teams, and generic urban challenges. The following model has extended to political history and social realities. The next version focuses on Milwaukee as a metaphor, depicting the city as a representation of broader American tensions.
The series illustrates how local journalism can document emerging technologies without taking a promotional or adversarial stance. The goal of what has become an annual series has neither warned readers about AI nor celebrated it.
Instead, he used the interview format to observe technology evolve, year after year, under controlled editorial conditions. In doing so, it has created a record of change that is unusually visible compared to most reporting on AI advances.
The interviews also raise questions about the media’s role in public understanding of artificial intelligence. As the line between human and machine-generated language becomes less clear, the responsibility placed on newsrooms increases.
The Milwaukee Independent series shows how a news publication can maintain clarity by emphasizing transparency, consistency and context over novelty.
In retrospect, the three April Fools interviews form a narrative about acceleration. They trace the transition from mechanical responses to interpretive fluidity, from novelty to ubiquity, and from external observation to integrated commentary.
What began as a humorous experiment is now a longitudinal snapshot of how quickly AI has entered public life and how one local newsroom has chosen to report on this change.
The series does not pretend that AI becomes human. Instead, it shows how language generation tools have changed the texture of public discourse. For the Milwaukee Independent, the annual interview remains a means of assessing this evolution, using the city itself as a constant through which technological change is measured.
At a time when competing artificial intelligences are advancing like a Cold War-era arms race, this editorial work serves as both an observation and a reminder. Progress is not only documented in tech labs or company announcements, but also in the constant accumulation of conversations between a city and the technology that now helps describe it.