Flipping the Circle: A Political Thriller

By Michael Leppert

“People don’t often think of corruption or white-collar crap having an actual crime scene, but the Winner’s Circle was the scene of this one.”

Will O’Courtney is the ultimate insider. Having worked as an experienced contract lobbyist in Indianapolis for over a decade, he knows all the ins and outs of back-room deals and trading information. Shortly after his divorce is finalized, Will resolves to turn his life around, and just when he starts to think of leaving the winning course, he lands a contract with a national tobacco company that would change his life forever. 

But when he discovers a scheme involving potential legislation for the monopoly of e-liquid tobacco products in the state, he finds out that malfeasance reaches the highest levels of government. Choosing to expose the seedy corruption behind closed doors in the Indiana Statehouse, Will becomes a whistleblower disguised as a lobbyist. 

As he deals with suspect colleagues, wondering who he can and cannot trust, Will finds himself falling in love with a sprightly and spiritual young woman, who ultimately leads him to see and uncover the deep cracks along the Winner’s Circle and leave it for good.

Set against the backdrop of contemporary events, Michael Leppert's intelligent and chilling thriller will leave you wanting more. 

Michael lives in a historic neighborhood in downtown Indianapolis with his wife, Amy Levander, and their rescue dog, Birdie. Flipping the Circle is his debut novel.

• Language: English
• Publisher: Greenleaf Book Group
• Release date: Nov 2, 2021
• ISBN: 9781632994387

Book preview

1

Offtrack betting parlors are dreadful places. They are often smoke-filled, dirty, and depressing. If the smokiness or filth doesn’t bring you down, the fact that almost everyone in the room is losing money will.

The Winner’s Circle was a little bit different than the standard OTB, though. It was new, and it was clean. Okay, it was clean looking. The smoke filtration system was better than those of the old days, when most gamblers just didn’t give a shit that they smelled like the bottom of a dirty ashtray. There was an actual menu with actual food on it. Expensive wine and scotch were available, presumably for the big spenders or big winners, not that many visited very often.

With its downtown Indianapolis location, the overhead was high. The gaming available didn’t attract crowds the way a craps or a blackjack table or even poker room might. Most of the food spoiled before anyone bought it. And anyway, the regulars preferred a hot dog with their cheap Smirnoff vodka or Miller Lite.

After a year or two, the casual observer might wonder how the generic place stayed in business. But there was a reason it remained. A few reasons, really, and only a few people knew what those reasons were.

To passersby, it’s just a bar like any other bar. It’s on a city street like any other city street. Anonymous, really, and all by design.

It was the scene of the crime. People don’t often think of corruption or white-collar crap having an actual crime scene, but the Winner’s Circle was the scene of such a crime. If I had to point to the spot, this would be it.

The bar was a playground, a place for the executive of the gaming company who owned it to hang out and get drunk and entertain his buddies. He stocked the bar with his favorite snobby wine and kept it on the shelf to impress people. Every staff member in the place, from the host at the front door to the after-hours cleaning crew, knew who their most important customers were. There weren’t too many to remember.

I never actually met Karl Satterfield. I was around him dozens of times, but we didn’t shake hands once. Everyone considered him one of the guys even though he was also thought to be the owner of the gaming company that owned the Winner’s Circle as well as the two casinos that were strategically located about an hour outside of Indy in different directions.

He wasn’t either. Karl was a grifter of sorts, a quick-buck artist from the suit-wearing crowd. His colleagues back at the gaming company wore tailored suits and an ensemble of accessories. They used a bit too much aftershave, and they wore a gold bracelet on one wrist and some expensive Rolex-type watch on the other. They owned casinos, but they were venture capitalists and Wall Street types who only bet on sure things. They were not the stereotypical wise guys of Rat Pack Vegas lore.

Karl’s job was to find, create, and—most of all—protect those sure things for his bosses. Sometimes he might find or create one for himself along the way, and why shouldn’t he? This was America, after all.

In Indy, he was a big deal. He acted like he owned the gaming company and people rarely asked if he did or not. I’m sure when they did, Karl lied about his status, but I don’t imagine he had to very often. He was surrounded by people who wanted to believe that he was a big deal.

The Winner’s Circle had a VIP section like every other casino does. This was Karl’s wing of the joint. He would wine and dine people there when he was bored or when a boss from the mothership told him to. But mainly, the VIP section was ground zero, the control center, home base of all of his evil little schemes that were the next great sure thing.

One Thursday night in January of 2012, long before anything inside seemed unusual to anyone, six or seven youngish white guys in cheap suits—for the most part—were sitting at a table in the VIP section. Their ties were loosened and their beers and cocktails were on the table as they watched college basketball on an oversize flat screen. This was Indiana, after all.

These guys were all members of the Indiana House of Representatives. They came over from the Indiana Statehouse, five blocks away. Across town, they were referred to as Representative Smith or Representative Jones. Maybe even Mr. Chairman or Your Honor. But at the Winner’s Circle, they were just Joe or Bob.

Karl and his chief lobbyist, Pauly James, and two other suits, lawyers from one of the firms in town, were sitting at the table behind them. There really is only one extremely important thing that we must have for this thing to get done, Karl said. We have to make sure there is no legitimate lobbyist in the Statehouse who is available and willing to fight us on it.

Pauly James jumped in. We have to find a way to clear the field, but it has to be cheap. We can’t go hiring every contractor to stand down. We have to give them a reason to stand down on their own. That’s why we want them all to buy into the business.

The first suit spoke up: What the hell do you mean, ‘buy into the business?’

Just what it sounds like, Pauly said. We’re going to sell shares in the business that will only exist if the law we want these guys to pass actually passes. And we are only going to sell these exclusive shares to the people we need out of the way.

The second suit interrupted: Sell these so-called shares for what?

Karl leaned back in his chair in a huff. Who gives a fuck? They’ll be paying us! We’ll offer a hundred shares of Company X for sale. We’ll say the shares are worth $1,000 each, maybe $10,000. And when this million-dollar company is worth a hundred million, these guys will feel like they hit the jackpot. But most of all, they’ll stay out of our way in the Statehouse while we get the bill passed.

So what do you need from us? the first suit chimed in again. Just the organizing structure, shareholder rights, all of that?

Yes, Pauly said. And the details on how we define the security firm but presented in such a way that no one can understand it.

That’s a piece of cake, suit two said. Convincing the entire Statehouse lobbying corps to buy into this shit will be the hard part.

Really? You overestimate these guys, Pauly said. They’ll line up to get in on this before I’m done. Keeping it secret is the real work.

No shit, Karl added. Secrets are the keys to the kingdom. As usual, I guess. Lawyers are supposed to specialize in this crap. I expect your work to help. With that, he got up and joined his young legislator guests at the basketball viewing party, one table over.

That was how it started. It was the first meaningful meeting. Without the meetings that followed, it would have been harmless. If someone along the way had given any of these grifters a compelling reason to stop, they probably would have. Looking back, it’s hard to believe no one did.

But any advice to stop was likely only given in an attempt to keep them out of trouble, or jail. Not because what they were trying to do was just wrong.

Right and wrong. Often the difference between the two is simply a matter of perspective. These crimes were like games to those committing them. To everyone else, not so much. Too often, nothing defines the difference so that it is clear to everyone.

Especially in my world.

2

On the far west side of town, on that same Thursday night, in the basement of a large Christian church, a dozen metal folding chairs were arranged in a circle. Seven or eight of the chairs were taken by a range of some pretty simple, average folks.

It’s a church basement like any other church basement. And it’s in a suburban neighborhood like any other suburban neighborhood.

Through the entrance of the door, a timid, good-looking, fortyish-year-old man appeared, seemingly uncertain if he was in the right place.

I was that man.

Okay, good-looking was a bit of a stretch. Reasonably presentable might have been more accurate. And fortyish was code for forty-three. I was legitimately in good health, though. The daily workouts and no-junk-food diet were the main causes of that.

The commoners in the chairs stopped their banter and looked up at me. A woman who appeared to be about seventy-five years old spoke up: Come on in, honey. You must be Will.

How did you—

Greg told us you might show up, she said. Enough about that, it’s time to get started. Find a seat.

Some might say that I was going through life changes at the time. They might cheer the things I did. Plenty of others would scorn the choices I made. But most people don’t know—or worse, remember—that any of it happened, even those it happened in front of.

During my decade and a half as a consultant (which is a code word for contract lobbyist), I had a business partner or two, and I hung up my name plate in a law firm or two. But in the game of lobbying, clients don’t hire firms or partnerships so much as they hire people. After a decade in the hallway, my reputation—and therefore my value—was pretty much set in stone.

My name is Will O’Courtney, short for William, like my dad, and his dad, although both of them went by Bill. You may have noticed by the names that I am Irish American. I stayed that course when I named my older son William, so we could call him Liam, and instead of naming my younger son Thomas, we named him Tomas.

But we aren’t just Irish, we are also Irish-Catholic. Mainly American and Irish, but sort of Catholic.

I never thought much of church. It might be because of my dad’s falling out with Catholicism when I was ten years old. For some reason, Dad seemed to blame the church for his life not turning out as he thought it should.

Church is a funny thing in America. Even for a guy like me, who had come to believe that religion in general was all just a bunch of nonsense, the God thing can be hard to avoid sometimes. It is all around us in the heartland.

There are two small towns where I spent—and now blame for— my youth. The first one is deep in the heart of Appalachia with a Baptist church every mile or so. The evangelical element of the culture never sat well with my transplant parents for the ten years we lived there. Dad used to say, Show me a born-again Christian, and I’ll show you a liar.

I came to learn that Dad was not always right and that some of his hostility toward the South had more to do with his own, self-generated unhappiness than any flaw in others. But as a child, I took his words literally, and I believed him.

When my teenage years started, we relocated from the Shenandoah Valley to Indiana and lived in a small town that was almost exclusively Catholic. Dad had already left the church, but Mom was still going. My older sisters and I became part-timers with her. All our new friends were there anyway. I grew from an awkward thirteen-year-old to a wannabe-cool kid at sixteen, and Saturday evening mass became a gathering spot for planning that evening’s debauchery. Jesus really didn’t have anything to do with it.

Of course, that was the scene where I found my first wife. People married young in small Indiana towns. It happened so often that it didn’t seem odd. And like so many of us from that small town, odds were that of every new young couple teaming up for that first life mistake, at least one of them would be Catholic. That’s how the church survived: inertia. I grew to believe that most of us knew the whole thing was bullshit.

But my first wife was a believer. Still is. Because of that, we raised our two sons in the church. I didn’t have a counterargument to make on that front, except for a godless one, which wasn’t all that compelling. The boys went to Catholic school. I mostly played along like a bunch of other sheep disguised as grown men. I coached youth sports and went to all of the church festivals. We hung around with other parents from school, who by definition were also Catholic. The groove was perfect for the wife because it was her choice. It was imperfect for me, though the people we spent time with were as fine a group as any other.

While I was somewhat Irish and sort of Catholic, I was excruciatingly Midwestern. After college at Indiana University, we were dug in on the west side of the big city. At the time, the big city was Indianapolis. I giggle when I think about how big I thought this town was. The skyline had a couple dozen buildings with more than ten floors, a half-dozen with more than twenty, and three with more than thirty.

Indy has an NFL team. And in the young, white, Catholic culture of the early ‘90s, the NFL might as well have been its own religion. As that character in the old Albert Brooks movie said about the league, They own a day of the week. It used to belong to God. Now it’s theirs.

That’s what the Colts were for me. Success in my life was having a man cave, which was decorated with Colts gear signed by all the greats, mainly from the Peyton Manning era. I had a great collection of otherwise worthless shit that made me feel like I was more a part of the team than my friends were. Of course, these friends were exactly equal to me in our complete lack of influence on the game.

When I walked into that Christian church basement on the west side of town, the divorce from my first wife was final. I’d recycled all my business partners and ended up at what I vowed would be my last firm. I’d quit smoking and drinking. I was exercising every day and eating healthy food. Hell, I’d even lost interest in gambling. I was starting a new way forward with all of the aforementioned virtues. The only thing left in my life that might have been in conflict with what I referred to as my soul was my profession.

I wasn’t convinced I could keep doing it. If I kept at it, I wasn’t sure what kind of clients I could continue to take—or would take me. But I had gotten used to my income, and my kids were getting ready to go to college, and well, you know how this part of the story goes.

Lobbying wasn’t fun for me like it used to be. Maybe I was getting old, or maybe I was growing up.

At lunch one day with Greg Bryant, one of my old friends from the west side, I told him how I didn’t know if I could stay the course professionally. Greg didn’t know the first thing about politics or government or lobbying.

You need to quit bitching and whining about your rotten lot in life, Greg said sarcastically. You’ve got it so fucking bad; I don’t know how you get out of bed in the morning.

A horrifying-looking man, Greg Bryant stood six feet four, was bald-headed and beard-faced, and both of his arms were covered in ink. He was one of the Catholic mafia whose kids went to school with mine. He was the one friend who survived my divorce, but only because he was getting dumped at the same time. For the better part of a solid bad year, we really didn’t have anyone but each other.

We got together once a week or so. It was a routine that started as a chance for us to bitch about our ex-wives, but that got old pretty fast, so we used the time to bitch about anything and everything else.

Greg told me he knew about a support group or a Bible study group—I can’t even remember what he called it that day. A group of people working on their spiritual journey met in the basement of Grace Memorial Episcopal Church.

He’d attended a few meetings the year before, but his shift at work changed, and he wasn’t able to continue so he fell out of the routine. He thought it was a group of otherwise sane people who got together once a week to talk about God, and how to improve their contact with him … or her … or it.

It wasn’t just for Christians. Even one of the group leaders was Jewish. Weird.

The folks at Grace Memorial will come up with some great ways to teach you how to shut the fuck up, he said.

That’s just what I’m looking for, a group of people to run their mouths at me, I said with a dismissive huff. I get freed from the one person I couldn’t listen to anymore, and your genius advice is to replace her with ten strangers?

He laughed at me and said, Don’t be such a pussy. Trust me. Just sit there and listen for a meeting or two. How exactly do you plan to find your soul on your own when you don’t even know where to look?

All right, smartass. Next week. Two weeks tops. I’m an expert at bullshit, you know. I won’t need any more than that to decide if it’s worth a third. You, on the other hand, are so damn dumb you wouldn’t know the difference between BS and the gospel, I uttered with a defeated tone of agreement. I just show up?

I’ll let them know you’re coming, and yes, just show up. That will be a miracle all by itself. I’ll see you in a couple of weeks.

And that’s how I ended up in the doorway of that church basement. I looked lost because I was. I needed career advice, but there I was at a church support group. Someone worse off than me sent me there, and by the looks of it, the people gathered there were as bad or worse than he was.

The good news was that at first glance, the group looked almost perfectly diverse. There were a couple old folks, a couple of young women, a couple of black people.

The old lady who told me to come in said, We’re gonna pick up where we left off last week. Will, we were talking about how people are born with a concept of God. That concept may change a lot over time, and it may change for a lot of reasons, but for most people, some concept of God is always there.

Oh my God! That was my immediate thought. But I was already in a chair.

Then a young lady started talking. She was maybe twenty-five, wearing faded blue jeans and an oversize hoodie that she probably hadn’t washed in the last ten wears. She could be pretty, but she wasn’t trying. It looked like she had combed her shoulder-length hair straight down right after a shower and let it dry. No makeup. Her fingernails were elaborately painted, each a different color. And I couldn’t take my eyes off her flip-flops.

It was cold outside. Why flip-flops? I then started to notice everyone’s footwear. There were work boots, New Balance tennis shoes, some overshined Italian leather shoes that belonged with a tuxedo. I wondered why I was suddenly looking at people’s shoes.

I was hanging my head when I was supposed to be pretending to listen. Weird. That wasn’t me. I needed to get it together. I had to consciously get my head up and focus on what the young lady was saying.

I don’t think the God my parents wanted me to worship was the one who belonged to me, she said.

What the hell did she say? Why was everyone nodding at that? I became curious in a frustrated, angry kind of way, but curious all the same.

The longer she talked the more I listened. The longer I listened, the more mature and pretty she seemed to become. Whatever she was saying had quickly turned into hypnotic noise, as if there weren’t any actual words coming out of her mouth. There was something about the way she spoke. It was slow and deliberate but not tense or anxious. Easy is the best word for it. She spoke with an easy gait. Until she ended with, And I’ve gotten into the habit of thinking about my God immediately, whenever I’m faced with a disturbance of any kind.

In about ninety seconds, she transformed from my first impression of might be pretty into an expanse of overwhelming curiosity. I wish she hadn’t stopped talking. And I wasn’t even listening to her words.

This young woman was reason enough for me to come back next week.

3

After college, I didn’t have a long list of job opportunities, but I ended up working for the State of Indiana. With a base salary of $15,000, that job was enough at the time. I had no five- or ten-year plan on the career front, but looking back, showing up and giving a shit coupled with above-average intelligence was a pretty potent combination for success in government service.

By the time I was thirty, I was running a state agency and rubbing elbows with the most important people in government. I had not arrived on that scene through politics, which was an advantage and a handicap at the same time. It was an advantage in that people assumed I had gotten the job because I was smart, not through connections. But the main reason I had risen was because I possessed the most valuable skill: communication. Being able to speak publicly or write coherently are things few people do well. I didn’t know that at the time.

My lack of a political connection was a handicap in many ways. For one, the upper echelon of the Democrat party never really trusted me. I wasn’t one of them. I hadn’t worked on campaigns. I didn’t come from money. I was never targeted as a campaign contributor, and so the money I now spent was new money. New money is less politically reliable than old money. And I had one major flaw: sometimes I disagreed with a partisan stance if I thought it was a stupid idea. That, specifically, was a dangerous thing for someone who had no built-in protection from having their ass fired for popping off in the wrong room at the wrong time.

That Democrats even controlled the governor’s office seems crazy now, a dozen years later.

Getting canned for speaking up was always a possibility for me, and there were a couple of times that I know of when that very discussion took place among the lower-level staff in the governor’s office. But let’s face it, most politicians are punks. Firing someone who might be smarter than they are takes balls, and most of them don’t have balls.

I’m a big believer in firing people who step out of line. So is the entire private sector. But bureaucrats are just weak souls usually. Which was another reason a guy like me could rise so quickly.

Ten years into my government career, I was making $75,000 a year, and I had gone as far as I could. The governor was two years away from retirement, and whoever replaced him would not keep me.

In 2002, I had a chance to become a consultant and finally make some real money. That’s how I ended up in the hallway, as we referred to it. Some people called it the lobby, but in the Indiana Statehouse, it was the hallway.

In the hallway, I often was the guy who would come up with a client’s or a campaign’s story. Why would a company need a tax break? Between you and me, it was so they could make, keep, or save money. But the story was always more along the lines of so we can reinvest in the community or so we can train more workers so their families can improve their incomes or because there are safety and security needs that cost money, and we want to protect the public.

You get the point. There was always some reason why a company or an industry needed a law tweaked. If I couldn’t come up with some believable BS spin for why I was asking the Indiana General Assembly to change a law, then I was worthless.

Or, heaven forbid, the idea was just that bad.

The story had to be short so it could be repeated and repeated and repeated. The stories were much like slogans or marketing pitches. Make America Great Again or It’s the economy, stupid are good examples of political slogans that became pitches. But in our world, they were lobbying stories. The more often they were repeated, the more believable they became.

Guys like Karl Satterfield tended to be the idea men. They were also almost never seen in the Statehouse. He was the type that would come up with the brainchild of new laws and regulations to make himself and his partners rich—or richer.

Coming up with the story was a strategy older than I was, but it turned out I was pretty good. But Pauly James was the best in the business.

Pauly specialized in sins—literally. He made his fortune in the contract lobbying business by advocating for alcohol and gaming interests. And he had grown into looking the part over the years. Spending one’s days in support of more booze and betting usually leads to a transformation of one’s soul and one’s appearance. He could lose fifty pounds and still be round. If he wore a three-piece suit, he might look like a casino boss—or Boss Hogg.

Without the suit, he looked more like Tommy Boy. He was everything the average American thought of when the word lobbyist was used. He looked like a Bubba. As stereotypes go, as a young man he was the guy in the fraternity house winning the beer bong contests and thumbing his nose at campus rules. He was the guy supervising the all-night poker parties before poker was cool. He was the guy who only lost money so he could make the rest of the patsies at the table think the game was legit.

As a grown-up, he was still a partier. But he’d started making a fortune as one, so life was grand.

In addition to representing Karl Satterfield, Pauly also represented the liquor distributors. That business has always been as predictable as the sunrise. Drinkers drink. They drink in a good economy and a bad one. They drink in celebration and in sorrow. Again, those outside of the business miss something here: when there is a monopoly on who can sell the liquor to the liquor stores, bars, taverns, and restaurants, the only important part of the business is protecting the monopoly. That may sound easy, and it is easier than competing every day like in a true market, but Pauly and his clients did work at it. That work would look pretty sleazy to people on the street, though.

In Indiana, there are no limits on what a lobbyist can give a legislator—no matter if it’s a case of scotch to take home or a $500 bottle of wine at a Tuesday-night steak dinner. There are reporting requirements if the value of any gift or entertainment goes over a certain amount, but complying with those rules really didn’t matter much in Pauly’s world.

The reporting requirements were part of a self-reporting framework established by the legislature years before Pauly appeared on the scene. Self-reporting is very much like asking the fox to report to the chicken farmer how many hens he ate last night, and then having the farmer believe it. It’s a lot like those college poker games Pauly used to host. Guys like him reported just enough of their entertaining and gift-giving to make it seem like they were reporting everything. But of course they weren’t. Why would