What Would Rita Crundwell Do?

Photo by Vadim Bogulov on Unsplash

On December 12, well before Biden commuted the sentences of 37 death row prisoners, he commuted those of 1,499 other people. Biden’s move that day was part of the largest single act of clemency in modern history. And on that notable day, one of the people whose sentences he commuted was Rita Crundwell.

I’d only learned about Crundwell recently, while listening to an episode of the Podcast Swindled, where the host told her story. Through the 1980s, 1990s, and into the 2000s, Crundwell was the treasurer and comptroller for the town of Dixon, Illinois, with a population of 15,144 in 1990.

In this role, on December 8, 1990, Crundwell opened a secret bank account called the Reserve Sewer Capital Development Account, making it appear to be a Dixon city account. Over the years, she used it to pay herself for bogus state invoices for non-existent projects. She stole from Dixon an average of $2.5 million per year, totaling a staggering $53.7 million by the time she was caught in 2012. Most of the money went to growing her Quarter Horse breeding operation, as well as to managing her extravagant lifestyle. That lifestyle included multiple cars, a second home, vast plots of land, and a mobile home worth more than $2 million.

I was thinking about Rita while I was checking out at the supermarket the other day. She somehow popped into my mind when I saw a gallon of milk I’d forgotten I’d tucked away on the bottom of my cart. I’d carefully placed it there a few minutes earlier so as not to crush the strangely soft sandwich bread I was purchasing for my kids. I dutifully took the milk out from under the cart and placed it on the belt to be scanned, wondering idly if the cashier would have noticed if I hadn’t.

As I was quietly congratulating myself for being such an upstanding and honest person, I had a strange thought. Would Rita Crundwell have taken the milk out to pay for it too?

Let’s not mince words here. The scale of Crundwell’s theft is difficult to comprehend. She systematically drained her small town's finances for decades, affecting services, infrastructure, and the lives of thousands of residents. She also lived among these same people, presumably interacting with them regularly at grocery stores, gas stations, and community events. She showed up to work, maintained relationships, and largely functioned as a regular member of society, all while orchestrating one of the largest municipal frauds in American history.

As I paid for my milk. I couldn’t help but wonder whether, over the three decades during which she was stealing money from Dixon’s residents, Rita ever found herself in a similar situation. As a matter of sheer probability, it seems likely that sometime over that time span, she did. Maybe it was the choice of whether to pay for milk or to sneak it past the cashier, or maybe she was walking behind someone one day and a ten-dollar bill fell out of the person’s pocket. Did she return it to the person?

The truth is, I don’t know. Rita might well have stolen the milk and kept the $10 bill. And if she did, that would align with what we know about her character as someone who knowingly and repeatedly violated both laws and trust. Yet the fact that we can’t know for sure suggests just how little we truly understand about human behavior.

History is full of examples of people whose actions defy easy categorization. Al Capone ran a soup kitchen, and the Japanese mafia, the Yakuza, helped with tsunami relief efforts in 2011. More simply, a business executive might be extraordinarily kind to their employees while orchestrating environmental disasters. A corrupt politician might champion and genuinely care about certain social causes while accepting bribes that harm some of their constituents. These contradictions don't excuse wrongdoing, but they challenge our tendency to view character as something fixed, absolute, and classifiable.

It’d be easy to walk away from this observation after acknowledging the important, but rather facile, point that people aren’t all good or all bad. But there’s a more complex question here too. That is, how much good does it take to make someone “good”? And how much bad does it take to make someone “bad”? And, especially for the not-so-religious among us, who decides?

When we encounter stories of fraud, corruption, betrayal, or worse we often rush to make sweeping judgments about the perpetrator's character. Maybe it’s the local bank manager who approves fraudulent loans but also organizes food drives and mentors troubled youth. Or maybe it’s the devoted parent who has an affair. Or maybe it’s the person who disagrees with you politically.

Even the legal system, in providing clear boundaries for criminal behavior, allows for some complexity. After all, presumably Biden didn’t commute Crundwell’s sentence thinking she’d go on to commit more crimes.

Let me be clear. I’m not suggesting the townsfolk of Dixon should welcome her back with open arms. I’m saying that the reality of human nature is far messier than our simple moral categories suggest. Moreover, I may have paid for the milk that day, but I’ve made my share of decisions that some probably wouldn’t see as praiseworthy. Perhaps the next time we find ourselves confidently judging someone's character, we might pause to consider the ethical choices in our own lives, and how much of another person's moral life remains forever outside our view.