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Lies That Chelsea Handler Told Me - Chelsea's Family, Friends [53]

By Root 626 0
Knowing that I was delivering nothing she wanted to hear, I decided I should probably build up as much goodwill as I could, so I let her do the honors.

“I lost ten thousand dollars,” she said.

Uh… what? I’m sorry, it sounded like you said you lost ten thousand dollars, but I know there’s no way that’s possible, because we don’t have ten thousand dollars for you to lose. I know some of you are thinking, “What do you mean you don’t have ten thousand dollars to lose? That’s nothing. You’re on TV and rich.” One of those is true. Let’s just say that with a lot of my checks, after I pay The Man, my agent, lawyer, and manager, I barely have enough left over to get drunk. But make no mistake: ten thousand dollars is a lot of fucking money.

“I don’t understand,” I said. “How did you lose ten thousand dollars?”

“Well, Chelsea and I bet on a basketball game last week and won.” What? They bet a basketball game last week? How did I not know about that? “We bet one more Monday and won.” What in the fuck is going on here? “So, I thought I would try one on my own, and I lost. I’m so sorry, baby. I don’t know what I was thinking. I was winning. It all seemed so easy, like I could never lose.”

Oh. My. God. This was not the conversation I thought I was going to have. Ten thousand dollars?

I called Chelsea. “Beth lost ten thousand dollars.”

Silence.

“Did you hear what I said?”

“I heard you,” she responded. “That’s not good.”

“No shit that’s not good. Why were you guys gambling?”

“Well, every fake bet I made I would have won, so I thought I’d try a couple of real ones,” she explained. “Beth kept calling and calling about when we were betting, so I let her bet with me. Ten thousand dollars. Wow. That’s a lot of money. I’ll call you back.”

Fifteen minutes later I got this text: It’s not $10K. It’s $15K. His name is Trent. 310-xxx-xxxx. I’m really sorry about this.”

Great. Fifteen thousand I didn’t have that I needed to shell over to a bookie. So I called him. I figured I could explain the situation and tell him that I’d pay it off in two installments. Now, I’ve been around enough bookies to know that normally there’s no way they would let that happen, but I figured I would drop Chelsea’s name and the guy would cut me some slack. I’ll cut right to the only quote you need to know from that conversation.

“I don’t care if you’re friends with the Pope. It’s fifteen K all at the same time.”

There was no getting out of this. Fifteen thousand dollars basically would wipe out my little cushion. But as much as we couldn’t afford to pay this guy, we had to pay this guy. Trent didn’t strike me as a dude who was going to let $15K just walk away. The next day, I set up a time to go over to his house and then went to the bank to get the money.

You ever write a check big enough for you not to want to let go of it? Imagine that… but with cash. I had fifteen thousand dollars in cash in my hand. I’d be lying if I told you the idea of driving to Mexico and seeing how long I could be drunk off $15K didn’t at least flash through my mind. And by flash, I mean I thought about it for about twenty-five minutes.

I drove up to Trent’s house in the Hollywood Hills; he buzzed me in at the gate and told me that he was in the back by the pool. As I was walking around the house all I could think was how I’d dug my own grave on this one. I never spoke up and because of that I was out $15K. I also decided that, to save my own ass, I would never tell Beth about the joke. Ever. That was the one good thing. She felt she had to make it up to me because she was the one who’d fucked up.

Nothing in the world could’ve prepared me for what I saw when I turned the corner and entered Trent’s backyard. It was Chelsea and Beth. Sitting on chairs by the pool.

“What’s up, asshole?” Chelsea said.

I was too stunned to speak.

They had set me up from the beginning. As soon as I had told Beth that Chelsea was a big-time gambler, Chelsea pulled the ol’ switcheroo. That tricky bitch.

Who knows? Maybe I am adopted.

Josh should be ashamed of himself. His wife is the sweetest

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