Billionaire Cashback System: I Can't Go Broke!-Chapter 53: Ridgemont

The course was in Westchester, forty minutes out of the city on a Saturday morning that had decided to be grey about it — overcast, cool, light that made everything look slightly underexposed.

Ryan had taken a car up. He arrived at Ridgemont at ten to eight and immediately understood that this was not the kind of golf club you knew about from the road.

The entrance was a break in a tree line, a long private drive, and then a clubhouse that looked like someone had taken an old English manor and moved it to New York without explaining why.

Stone facade, dark trim, a parking area with cars that made no noise about what they cost.

He checked in at the front desk and was pointed toward the pro shop, where Richard had apparently arranged for equipment rental and a caddie, as promised.

The caddie was a kid named Marcus, maybe twenty-two. He assessed Ryan once — the rental clubs, the shoes that were correct but new — and said nothing about any of it, which Ryan appreciated.

Richard was on the putting green with two other men when Ryan came out. He introduced them as Carver — the same compact man from the dinner — and a taller, looser man named Holt who had the handshake of a man who didn’t think handshakes required effort.

"Ryan," Richard said. "Good. You’re early."

"You said eight."

"Few interpret that as eight-fifteen." He looked Ryan over. "You get clubs sorted?"

"They set me up inside."

"Marcus is good," Richard said. "He’ll keep you out of serious trouble." He said it with easy tone from the dinner — less hostile, just consistently positioned from slightly above. He turned back to Carver and resumed something they’d been in the middle of.

Ryan stood at the edge of the green and watched Holt line up a putt and miss it by three inches.

---

The first hole was a par four, moderate length, straightforward by the standards of everyone present except Ryan.

Richard went first. His swing was practiced and unhurried, the ball going straight and long, landing in the fairway with room to spare. Carver and Holt were similar — not professionals, but men who had spent enough Saturday mornings on courses to have the mechanics settled in their bodies.

Marcus handed Ryan a driver and stood beside him.

"First time?" he said, low enough that it wasn’t for anyone else.

"Roughly."

Marcus looked at the fairway, then back at Ryan. He spent thirty seconds explaining the grip, the stance, the one thing Ryan needed to focus on which was keeping his head down through contact. Then he stepped back.

Ryan stepped up.

He thought about what Marcus had said, decided not to think about it too hard, and swung.

The ball went right. Not catastrophically right, not into the trees, but right enough that it was off the fairway and sitting in the first cut of rough.

"Not bad," Marcus said with neutrality, he had seen worse.

Richard glanced back. "We’ll get you there," he said. Friendly. Generous. Particular generosity that enjoys having something to be generous about.

Ryan picked up his bag and walked.

---

By the fourth hole Ryan had found something close to a rhythm.

Not a good one necessarily — his drives were inconsistent and his short game was largely theoretical — but he was making contact cleanly most of the time and Marcus had a way of positioning him before each shot so that even the imperfect swings ended up somewhere manageable.

The conversation between Richard, Carver, and Holt moved how conversation moves on golf courses — loose, topic-jumping, occasionally landing on business but not staying there.

Richard told a story about a deal that had gone sideways in a way that was funny now and hadn’t been at the time. Carver said something about a board meeting that made Holt laugh.

Ryan contributed enough to exist in the group without performing membership in it.

He was watching Carver line up a shot on the fifth tee when he heard a cart on the path behind them.

He turned.

There were two carts. The one in front had two women in it he didn’t recognize.

The one behind it had Diana.

She was in the passenger seat, her caddie driving. She wore slim white trousers and a polo in a deep navy, fitted through the shoulders, and she had sunglasses pushed up into her hair and a golf glove on her left hand.

The outfit was the right outfit for the setting in every technical sense and it was also not doing a particularly thorough job at its secondary function, which apparently was to keep Ryan’s attention where it belonged.

He turned back toward the fairway.

"Diana plays on Saturdays when the schedule allows," Richard said beside him, with awareness, he had noticed Ryan notice. "She’s better than I am. I don’t advertise that."

"Smart," Ryan said.

Richard smiled, tight and real this time, and looked at his wife’s cart as it pulled past. Something moved across his face — complicated, quick — and then it was gone and he was watching Carver’s shot.

---

They crossed paths with Diana’s group at the seventh hole, where the paths converged near a water feature and both groups paused for the cart traffic.

She walked over.

"How’s he doing," she said to Marcus, who was standing near Ryan.

"Improving," Marcus said.

"High praise," Ryan said.

Diana looked at him over the top of her sunglasses. "Richard giving you a hard time?"

"Just enough."

Richard appeared at Diana’s shoulder. Something in his posture shifted when he stood next to her — not affectionate exactly, more territorial in the absent, habitual way. He said something to her about the back nine, she responded, they had a brief exchange that was entirely functional, and then her group was moving again and Diana was stepping away. 𝘧𝘳𝘦ℯ𝓌𝘦𝒷𝘯𝑜𝑣𝘦𝓁.𝒸𝘰𝓂

She glanced back once at Ryan — brief, direct — and then she was in the cart and they were gone down the adjacent path.

Ryan watched the cart for half a second longer than was necessary.

Then Marcus handed him a seven-iron and pointed at the green.

They finished the front nine at half past ten and stopped at the halfway house for coffee and whatever the club was offering for food.

Richard and Holt got into a detailed conversation about a rezoning issue that required maps on a phone and both of their full attention. Carver had gone to use the facilities.

Ryan poured coffee and stood at the rail looking out over the back nine, which disappeared into the tree line about four hundred yards out.

"You’re better than you were on the first hole."

He turned.

Diana was there, alone, her own coffee in hand, her group apparently occupied elsewhere. She had pushed the sunglasses up into her hair again and looked at the same stretch of fairway he’d been looking at.

"Marcus is good," Ryan said.

"He is." She took a sip of her coffee. A beat passed. "Last night."

Ryan looked at her.

"I was — I’d had a few drinks by the end." She said it practically, like she was accounting for something. "Under the table. That was — I don’t want you to read into that."

"I didn’t," Ryan said.

She looked at him. "Good."

"The bathroom was nothing either," he said.

"It was nothing," she agreed.

"Circumstances," he said.

"Exactly."

Another beat. She was looking at the fairway again. He was looking at the fairway too.

"You handled Richard well last night," she said.

"He’s fine."

"He’s a lot of things. Fine is one of them." She turned her coffee in her hands. "He thinks the investment is too early."

"You told me."

"He told you, at dinner."

"He did."

"He’s not wrong that it’s high risk," she said. "He’s just wrong about the team." She said it with finality, the way she said most things, like the sentence was a door closing. "Iralis alone is worth the exposure."

"I’ll tell her you said that."

"Don’t. She’ll use it in a salary renegotiation." The corner of her mouth moved. Close to a smile — a concession in the direction of one.

Ryan looked at her — the line of her profile, the way the grey morning light sat on her face, the particular stillness she carried that made rooms quiet around her.

She turned and caught him looking.

Neither of them said anything.

He could still remember vividly, the warmth of her pressed back against him and the silence afterward and the way she had said ’that’s up to you’ like she was leaving a door open and then walking away from it.

She was standing close enough right now that there were three inches of air between their arms on the railing.

"I meant what I said," she said. Her voice was even. "Don’t read into things."

"I’m not reading into anything," Ryan said. "I’m just standing here drinking my coffee."

She looked at him for a moment.

"Good," she said.

Exactly how she’d said it before, and it landed the same way — like the word was doing two jobs at once, and she was aware of both of them, and she wasn’t going to address either one directly.

She straightened up from the railing.

"Back nine," she said, and walked back toward her group.

Ryan watched her go.

He took a long sip of his coffee, stared at the tree line, and said nothing to anyone.