He Played Poor for 99 Rounds, I Won on the Last One Chapter 01

He Played Poor for 99 Rounds, I Won on the Last One Chapter 01

Dorian Blackridge had always loved testing me.

Fresh out of college, he tried to saddle me with a five-million-dollar mortgage. When I refused, he turned around and bought Vanessa Hale a luxury villa outright for eight million—no hesitation, no conditions.

Then he handed me the deed, like it was some grand reveal.

“Celia,” he said, almost amused, “I’ve always been wealthy. I just played broke to test you.”

“Unfortunately, you failed. I’m disappointed. We’re done.”

I smiled back, just as lightly, and walked away without a trace of regret.

Funny thing was, I had been playing broke too.

Because I was the heiress of the Viremont family.

Four years later, we met again at the Apex Capital Summit.

Dorian had just broken into the top fifty on the National Wealth Index. He walked in with Vanessa on his arm, all elegance and polished charm.

When he spotted me—dressed simply, no jewelry, holding a child—his expression shifted instantly.

“Celia,” he drawled, strolling over, “you really went all out just to see me again. Even tracked me down here.”

His gaze flicked over me, dismissive.

“Let me save you the trouble. I’m on the Wealth Index now. You’re babysitting for someone else. We’re not even in the same world anymore, so don’t kid yourself.”

I didn’t bother responding.

Instead, I silently cursed my father for dragging me here. I’d carved out exactly one free day to spend with Elliot, and now it was being wasted on this circus.

…

Dorian entered the private reception lounge with Vanessa draped on his arm, looking every inch the rising star of high finance. As they passed the side lounge, his eyes landed on me immediately.

Of course they did.

I was sitting in the corner, Elliot in my arms, deliberately keeping to myself.

The plan had been simple—show up, make a brief appearance, and leave. No one important had arrived yet anyway.

Because I was holding my son, I hadn’t worn any jewelry. No visible markers of wealth. No effort to impress.

To Dorian, that translated into one thing.

Failure.

He strode toward me, his expression sharpening with disdain.

“So this is where you ended up,” he said, voice edged with ridicule. “Reduced to being someone’s nanny. Without me, you’re nothing.”

“Too bad you didn’t pass my test back then. Otherwise, the one standing next to me now would’ve been you.”

He tightened his grip on Vanessa’s hand, and added, “But in the end, it worked out. If it weren’t for you, I wouldn’t have found someone who actually loves me.”

Vanessa smiled sweetly, her tone soft but cutting.

“She must regret it every day. Honestly, it’s her own fault for not knowing what she had.”

Her gaze slid over me, slow and deliberate.

“Then again, this suits her. She looks right at home playing nanny.”

She turned to the venue staff passing by, her voice instantly sharper.

“Do you people even check who you’re letting in? This is a high-level event. If something goes wrong, are you prepared to take responsibility?”

A slight pause, then a cold directive.

“Get her out.”

My outfit, though understated, was custom-made by one of Italy’s top ateliers.

In the past two years, I’d taken over Viremont Holdings entirely, which meant I rarely appeared in public.

They didn’t recognize me.

And in a place like this, appearances dictated truth.

The staff stepped forward, their tone polite but firm. “Ma’am, I’m sorry, but unauthorized individuals aren’t allowed in this area.”

I didn’t move.

“I’m here for the summit,” I said calmly. “I have every right to be here.”

They hesitated. People who carried themselves like I did weren’t easy to dismiss outright.

But Dorian laughed, loud and cutting.

“You?” he said, as if I’d just told a joke. “You needed scholarships just to get through college, and now you’re claiming you belong on the Wealth Index?”

He tilted his head, eyes narrowing.

“If you’re really here for the summit, your name’s on the guest list, right?”

It wasn’t.

The Viremont name was listed—my father’s. It would only transfer to me once he officially retired this year.

My silence was all the confirmation he needed.

Dorian turned back to the staff, his tone dripping with authority.

“Let me make this clear. She missed her chance because she failed my test. Could’ve been Mrs. Blackridge.”

A smirk.

“But people like her? They’re always the same. Obsessed with money, short-sighted, incapable of holding onto real opportunity even when it’s handed to them.”

I had arrived early. The real power players hadn’t shown up yet. Most of the people present hovered around the lower end of the rankings, eager to align themselves upward.

A few recognized Dorian and eagerly joined in.

“Then she really blew it,” one of them said with a laugh. “Losing a guy like Mr. Blackridge? I’d regret that for life.”

“Weren’t they together for four years in college?” another added. “And she still couldn’t lock it down? That’s almost impressive.”

Dorian’s expression flickered—just for a second.

Back in college, he had pursued me with relentless intensity. We’d both hidden our backgrounds, living like ordinary students, falling into what felt like a real relationship.

For four years.

I went through ninety-eight of his so-called tests. Juggling part-time jobs, pushing my body past its limits, cutting ties, enduring injury, giving up opportunities that actually mattered.

All of it staged.

All of it deliberate.

And while I was struggling through the obstacles he designed, he was showering Vanessa with gifts—cars, properties, anything she wanted.

When I found out the truth, something in me went cold.

I refused the ninety-ninth test.

And I walked away.

No one noticed the shift in his expression. The room was still filled with laughter, still feeding on the spectacle.

Until his voice cut through it, suddenly sharp.

“That’s enough.”

“Get her out. I don’t want to see her.”