The next two weeks were some of the loneliest I’d ever known. I forced myself to stay gone a week longer with no contact just to give an impression. The bluff worked. When I landed in Boston, her driver was waiting on me at the airport. He stood next to his limo. “Mr. Finn?”

The window behind him rolled down slightly and Amanda’s emerald-green eyes smiled at me. We didn’t leave each other’s side for nearly a week.

A month later, she invited me to have dinner with her folks, private plane, helicopter, yacht, the Hamptons, all in a casual effort to meet the family. I was no dummy. Mr. Pickering had a file on me six inches thick. I was pretty certain he knew my grades in grammar school, how many pizzas I’d delivered, that I’d had my wisdom teeth pulled my senior year of high school, and he could recite my college transcripts from memory. He was either allowing me to come to dinner to publicly undress me in front of his daughter and show her the fraud I really was, or he was raising an eyebrow and wanting to know what I was made of. His future son-in-law might marry into this family, but he’d earn every penny of her money.

After kissing his daughter, he extended his hand and put his arm around me. “Charlie. Welcome. Come in. We’ve heard so much about you.” He could not have been warmer. My first thought was, This guy is good. Remind me to never play poker with him.

Too late. We were already playing.

I chose my words at dinner, speaking only when spoken to, responding to Amanda’s mom, who fired off most of the questions. These people had made up their minds long before I walked in that door, so I enjoyed my meal and answered honestly and casually. I figured that by not trying to impress her folks, I was actually doing a better job of impressing them—if that was possible. When asked, I gave the short details of my life—which I was pretty sure they already knew. Dad drove a cab but killed himself when he wrapped it around a concrete barrier with a blood alcohol of about .3. Mom worked two to four jobs to support us but followed Dad my junior year of high school. Three questions shy of acing the SAT. Harvard full ride. 4.0 GPA. Four-minute, seven-second mile. Would graduate a semester early.

Her mother raised a finger. “Following the death of your mother, who raised you? Supported you?”

“I did.”

“How did you survive? Buy food? Pay the power bill?”

“I delivered pizza and sold drugs.”

While she laughed at the joke, thinking I was making one, he sat back and smiled smugly—telling me he knew I was not.

Amanda’s dad poured wine for everyone at the table and saw it as his personal mission to stoop to the level of a butler and make sure everyone was sufficiently happy with his “house” wine, which, Amanda whispered, wholesaled at $200 a bottle. I didn’t touch it and every time he offered I declined.

He noticed my lack of consumption before we ate our salads and watched with curiosity as my wine sat untouched all night. When they lit the bananas Foster, he asked almost with disappointment, “Could we get you something else?”

This was it. His first push and I knew it. He was raising me. I shook my head and answered only what I was asked. “No thank you.”

Another push. A raise. “You don’t like my wine?”

I met his raise and raised again. “Don’t know. Haven’t tried it.”

He waited, eyeing the cards in his hand.

Amanda sipped and smiled. More amusement. She tapped my foot below the table.

A single shake of my head. “Don’t drink.”

He knew this, but rather than admit that, he raised his glass and toasted me and then his daughter and finally his wife and their Persian dog. I wouldn’t say that I won that hand as much as I had succeeded in earning myself a seat at the invite-only table.

Following dinner, we “retired” to his porch, looking out across the water. He offered me a cigar. Again, I refused. He rolled his around his mouth, lit it, and then sucked on it until the end glowed like a hot iron. Oddly, the color matched his eyes. Drawing several times on the Cuban, he exhaled and filled the air around us with a haze of smoke. “You don’t appear to have any vices, Charlie.”

I was in way over my head. Any idiot sitting in my chair knew that. This guy ate guys like me for breakfast and picked his teeth with what remained of our backbones. Somewhere around the third course, his stiffening body language told me that I’d be seeing less of Amanda following dinner. Little I could say or do would change that. He wanted someone strong but not someone who would so willingly challenge him—which is what I’d been doing all night. And he knew that. And he knew that I knew that.

Given that I could read the cards I’d been dealt, I again decided on the honest approach. I can’t really tell you why other than I had a pretty good feeling that this guy could read my bluffs far better than I could make them. Besides, I’d never had dinner with a man worth almost a billion.

Halfway through his cigar, he said, “Amanda tells me you’re a bit of a poker player.”

“I’ve played some.”

He pointed to a felt-covered table. An innocent fatherly face. “Shall we?”

I folded my legs and rested my hands in my lap. “No need.”

He studied his cigar, drawing deeply. I think he was starting to get irritated. “Really?”

“I made money by playing trust fund kids who viewed poker as entertainment. And I sincerely doubt you brought me here to entertain you.”

He chuckled, admiring the red tip. “You preyed on gullible people.”

“I provided a service to kids who were burning through Daddy’s money and should know better.”

“And you know better?”

“I saw an opportunity.”

He nodded. “And seized on it. I like that.” The innocence drained out. “I pay a lot of money for people who can read other people.”

“Mr. Pickering, I have the feeling you can read me a lot better than I can read you.”

He smiled and grabbed his imaginary chips off the table. “Touché.” He may not have liked me, but he admired me for folding my hand when faced with someone who held better cards. He glanced at me. The smoke exited his throat like a chimney. “Marshall. Call me Marshall.”

*  *  *

With her parents’ apparent approval, Amanda and I “dated” through our senior year. Harvard seemed impressed enough with my undergraduate record that they offered to take me in the MBA program, and while I didn’t know for sure, I was pretty well convinced that Marshall had more than just a little to do with it. After the first week of classes, Marshall called me into his office and made me a job offer I couldn’t refuse. I decided to play another hand and accepted.

Marshall ran money. His and others’. He also owned companies around the world. The more I got to know him, the more I came to realize that the story about his net worth being a billion was off by about $2 billion. There was a lot at stake. He had three billion reasons to choose wisely. Knowing this, he’d staffed his “firm” with young guys like me under the guise of training us. Mentoring us. Showing us the ropes out of the goodwill of his heart. In truth, he meant to run us through the wringer and see what we were made of. Owners of horses do the same thing. Fill their stable with the cream and see which Secretariat rises to the surface. Butchers also do this with meat they are about to tenderize. Pickering and Sons was a highly successful hedge fund in an era when most were folding up shop. It was also Marshall’s own private joke on the world. He had no sons. His entire life’s goal after becoming otherworldly wealthy was finding the one thing he couldn’t buy.

Someone to guard what he valued in his prolonged absence—i.e., his death.

He showed me around his office, introduced me to the guys, and then casually showed me my cubicle. Gone was the tender father from dinner, pouring wine and lighting cigars. “I have several hundred résumés, many better than yours, sitting on my desk. Each detailing why and how some young man is chomping at the bit to sit in this chair.” He spun the chair around. “Why don’t you take a turn?”