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He Bet on My Love, Then Lost Everything
He Bet on My Love, Then Lost Everything
Author: Winter

Chapter 1

Author: Winter
I set the frosting-smeared napkin on a silver tray and unpinned the enamel badge on my dress that read FUTURE MRS. CALLOWAY.

Sabrina was still laughing. She leaned against Luca and asked, “Elena’s really mad this time. Who’s volunteering to talk her down?”

Luca raised his whiskey toward Adrian. “Her fiancé, obviously. They’re getting married at St. Patrick’s next Saturday. Might as well get used to it now.”

Adrian didn’t come to me right away. He stared at the buttercream on his fingers as if the sight had finally caught up with him. Phones were still pointed in our direction, though, and he’d never lower his head with an audience watching. He cleaned his hand with a monogrammed handkerchief before approaching me. “All right, sweetheart. That’s enough.”

He said it as if I’d caused the scene.

“What’s enough?” I asked. “Your game, or my reaction to it?”

His expression flickered, but Luca stepped in before he could answer. “Don’t turn this into something it isn’t. Would Adrian have spent six months planning a wedding if he didn’t love you?”

“Exactly.” Sabrina rested her cheek against Luca’s shoulder, all polished sweetness. “Sure, Adrian approached you because of a bet, but then he fell in love with you. You got the happy ending. Why obsess over how it started?”

The emerald on her left hand flashed under the chandeliers. Four years earlier, Luca had asked her to help him set up his proposal to me. When I opened his bedroom door, I found them under the same blanket. Sabrina had been holding a camera, while Luca pulled a ring box from beneath the pillow and told me they’d wanted to capture how “cute” I looked when I got jealous.

I ended ten years of loving him that night.

Afterward, Sabrina told everyone I’d never learned to take a joke and that Luca had only fallen for her after I pushed him away. It wasn’t the first time she’d made me the punch line. In college, she told me a charity ball had a Roaring Twenties theme. I walked into a strict black-tie fundraiser in a beaded flapper dress while everyone else wore evening gowns. She filmed me freezing in the doorway and sent the clip to our alumni chat. When I told her to delete it, she teared up and said she’d mixed up the dress code. By the end of the night, everyone was asking me not to embarrass her.

Every one of her jokes ended the same way. Sabrina created the spectacle. I got hurt. Luca and Adrian explained that I was the one ruining the mood.

“Do you honestly believe saying you didn’t mean it erases what you did?” I asked her.

Her smile dimmed. “I’ve always treated you like family. How can you think I’m that awful?”

Luca’s face hardened at once. “She’s trying to explain, and you’re putting her on trial in front of everyone.”

Adrian frowned. “Elena, don’t turn our engagement party into a circus.”

I almost laughed. Ten minutes ago, he’d turned me into the evening’s entertainment. Now the circus was my fault.

Around us, the people who had toasted our future suddenly found their glasses fascinating. These were bankers, heirs, political donors, and old family friends. A few looked uncomfortable. None of them put down their phones.

That was the ugliest part. Adrian’s love hadn’t been entirely fake. He knew I hated sleeping with the closet door open. He’d flown to Milan on six hours’ notice when my father died, and he still carried the worn Saint Christopher medal my grandmother had pressed into his palm. But the second Luca questioned his pride, Adrian chose the approval of the room over the woman he claimed to love.

I removed the diamond clip that had caught frosting near my ear and slipped it into my clutch. When I headed for the exit, Adrian caught my elbow, then released me the moment I looked down at his hand.

“Where are you going?”

“Home.”

He lowered his voice. “Fine. Go cool off. The wedding isn’t canceled, though. My driver will pick you up Saturday morning.” After a pause, he added, “I’m still marrying you. What more do you want from me?”

[He thinks marriage is a blank check. As long as he signs it, I’m supposed to be grateful.]

I had been raised to believe marriage wasn’t a prize a man handed to a woman. It was an alliance built on mutual loyalty. Without respect, an alliance was just a contract waiting to be torn up.

Adrian knew almost nothing about the family I had left behind in Milan. He certainly didn’t know that some of the money and connections that had helped his company grow had quietly come through me.

Outside the hotel, rain glossed the Manhattan streets. The doorman put me in a black town car, and I finally checked my mother’s reply.

[If you leave him, the resources our family put behind Calloway Harbor won’t stay with the company. Are you sure this is what you want?]

I typed back without hesitating.

[I’m sure. I’m leaving.]
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  • He Bet on My Love, Then Lost Everything   Chapter 9

    One year later, the Genoa waterfront project opened to the public. The century-old brick walls of the warehouses had been preserved, while the seaward side had been replaced with sheets of glass. Harbor lights came alive along the coast as the press filmed me cutting the ribbon.My mother stood behind the crowd and raised her glass from a distance. She had never needed a stage to remind anyone who held the room.The project outperformed our first-year projections, and the board voted to place me in charge of Vitale Holdings’ next round of North American investments. When I returned to New York, it wasn’t for any man.At the opening press conference, a reporter asked whether the scandal surrounding my canceled wedding had inspired the project’s focus on public space. A year earlier, I would have smiled and changed the subject to protect everyone else.“No,” I said. “The project existed before the engagement ended. I’m simply done shelving my work for people who treat my loyalty like an

  • He Bet on My Love, Then Lost Everything   Chapter 8

    After the board suspended him, Adrian moved out of his West Village townhouse. The company-owned property, cars, and club memberships went into the restructuring. By the time he left, everything he still owned fit into a few boxes.While packing, he found a navy leather portfolio. Inside was the first European route plan I’d prepared for him and a pair of silver cuff links engraved with our wedding date.The inscription on the back read:[Wherever we go, we’re on the same team.]He sat on the floor for a long time. My messages to him used to be paragraphs: storm warnings, client preferences, board schedules, reminders about his mother’s medical appointments. Over the years, they had gotten shorter.The last one had arrived before the engagement party.[If they make me the joke again tonight, will you stand with me?]He’d been drinking with Luca and sent back one line.[Don’t create a problem before anything happens.]Adrian closed his eyes. I hadn’t denied him a chance. I had told him

  • He Bet on My Love, Then Lost Everything   Chapter 7

    When the lawsuit reached discovery, investigators recovered the group chat in full. From the college fundraiser video to the bedroom proposal stunt and the engagement cake, every joke had left a trail.Sabrina came up with the ideas. Luca turned them into games their entire circle could join. Adrian stayed quiet—or joined in—whenever he had the power to stop them.The messages from the night of our engagement party were especially clear.[Sabrina: What if she loses it in front of everyone?][Luca: She won’t risk the wedding.][Adrian: Don’t take it too far. She’s been under a lot of pressure.]Five minutes later, Luca had needled him.[Luca: Don’t tell me she’s already got you whipped.]Adrian had replied with a thumbs-down emoji.There were hundreds more. Sabrina had once posted a photo of me sitting alone at dinner after Adrian missed our anniversary.[Sabrina: Five minutes until she starts crying. Any bets?][Luca: Three.][Adrian: Knock it off.]Two minutes later, when Luca sent a

  • He Bet on My Love, Then Lost Everything   Chapter 6

    A week later, Calloway Harbor Group held an emergency board meeting. Bank representatives, investors, and independent directors filled both sides of the table. No one made small talk, and no one saved the head chair for Adrian.Marcus Reed, the board’s longest-serving director, pushed a file toward him.“Six years ago, this company was weeks from liquidation. Vitale Holdings guaranteed the first rescue facility.”Adrian looked up sharply.“Vitale Holdings?”Marcus stared at him. “You really didn’t know?”Adrian said nothing.Marcus pushed a second file across the table.“Four years ago, when the European routes were hemorrhaging money, Elena gave you the Vitale family’s priority berths in Genoa.”The third document was a client list. Marcus tapped it with one finger. “Seventeen of your twenty largest accounts came through her introductions. What exactly made you believe the business would keep running after she left?”Adrian’s hand tightened on the arm of his chair. “I never asked her

  • He Bet on My Love, Then Lost Everything   Chapter 5

    Mamma took me straight to the airport. By the time Adrian realized I wasn’t going back to the penthouse, my flight to Milan had already taken off.Adrian arrived at the airport anyway. He called me dozens of times...Adrian waited outside the airport until sunrise. He called me dozens of times and had his assistant contact private aviation companies to track my itinerary. He only stopped after Valentina warned him that continued surveillance could be treated as harassment.By the time he returned to Tribeca, the penthouse’s electronic lock had been changed. The building manager handed him a cardboard box. “Ms. Vitale revoked your guest access. These are the personal effects she left for you.”Inside were his shaving kit, several shirts, a spare car key, and the unfinished book of wedding vows.He stood in the hallway without moving. The first time he’d stayed over three years earlier, I’d cleared half the closet for him. He’d joked that he didn’t own enough to justify all that space. B

  • He Bet on My Love, Then Lost Everything   Chapter 4

    Luca looked down at me.“Two hours should be enough to teach you a lesson. Apologize to Sabrina, and we’ll call it even.”My lips were still numb from the cold, and my teeth chattered when I tried to answer.Sabrina stepped forward and slipped her arm through mine.“Luca, Adrian, stop. Elena didn’t mean any of this.”Then she turned to me with a soft smile.“We’re still best friends, right?”Before I could pull away, Sabrina slipped one arm around me and deliberately pressed her fingers into the fresh burn beneath my blouse.I cried out and shoved her away on instinct.Sabrina cried out and stumbled backward. Her eyes filled at once.“Elena, you still can’t forgive me?”Luca’s face hardened.“What the hell is wrong with you?”“She pressed on my burn.”“I didn’t,” Sabrina said quickly. “I was trying to help her.”Luca shoved me back.“Elena, how long are you going to keep this up?”My lower back hit the wall, right where the burn had already blistered. My breath caught, and my knees nea

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