You met on a dating site called "Sugar Daddy."
You're giving her money.
Up to $20,000 in four months?
You're here because you didn't pay him back 600 bucks.
Dude, you can really do better than trying to buy a woman's affections.
I'm just expecting to, uh, get my money back.
-Do you think this woman loves anybody? -[James] No, Your Honor.
You gonna like, try to buy her dinner tonight?
Yeah. [chuckles]
He's like, yes.
Was that a "yes"?
Ooph, all right.
[narrator] Now, on Tribunal Justice...
[theme music playing]
[narrator] Today's case was filed in Pensacola, Florida.
Your Honor, this is Case #3091, Pritchard versus Ashcraft.
All parties have been sworn in.
-Thank you, Cassandra. -You're welcome.
You may be seated.
Mr. Pritchard and Ms. Ashcraft,
you met on a dating site called "Sugar Daddy."
[James chuckles]
You, sir, after spending, oh, you say between $10,000 and $20,000
on her in a period of four months,
you actually loaned her $600 to pay her rent.
And you say she promised to repay you. She hasn't.
You spent so much money on her, so really,
this was you giving her money and her promising to repay,
and that's what was different about this.
Ma'am, what you say is that you don't owe him anything
because this $600 was no different than the $10,000 or $20,000
that he spent on you to support your "Sugar Baby" lifestyle,
that he's just doing this to see you again. You owe nothing.
So, let's go through your situation.
You guys meet on this Sugar Daddy website in June of 2024, sir?
Yes, Your Honor.
[DiMango] And what do you do? You start texting each other?
Yes, Your Honor.
[DiMango] Do you talk, as well, on the phone?
Sometimes, over the phone,
uh, before she finally became comfortable
with us moving forward
with going out on dates, um, events...
You go to dinner, you pay. She goes...
You go once in a while. She pays, she'll buy you a gift.
Right? Did that ever happen with you?
It was always me paying for everything,
and always me giving 100%.
-Well, you were a Sugar Daddy. -[James] Yes, Your Honor.
So, during this time now, you finally meet in person when? September?
-No, in June, Your Honor. Yeah. -In June. You meet in June.
Does it carry through into a romantic relationship?
It was on and off.
[DiMango] What do you mean "on and off"?
[James] What would happen was we would make plans.
And we would come up with a time that I would come pick her up
for us to go out. And almost to her place,
and she's still not awake 'cause she's been...
How many times would this happen?
Between June and, uh, September,
I'd say somewhere around eight to ten times.
[DiMango] How many times did you need it to happen to you?
Being stood up?
It was a vicious circle. We would...
[DiMango] No, it wasn't vicious. It was what you were doing to yourself.
Let me move on before I get too agitated.
So now, apparently, you tried this romantic relationship.
So, let me move over to you.
How do you define a romantic relationship?
Going on dates and spending time together.
Really? And do you share anything in these dates?
Gifts, or dinners, or money?
No, because that's not what you're in this for. Correct?
[Isabella] I did.
[DiMango] What did you give him?
He actually said, "Hey, we're past Christmas, it's January.
Where's my Christmas gift?"
You didn't even give him a Christmas present.
So now, we're in November.
You're putting her up in an apartment, right?
-You're paying for an apartment for her. -Yes, Your Honor.
But he's not allowed to come in the apartment.
Would I be correct about that?
-He... -[DiMango] Yes, I am.
What are you taking time to think about?
I could just pull up your text messages
where you say to your cousin who lives with you, don't let him in.
He's paying for your apartment.
He's not allowed in. He doesn't have a key.
-Who's paying for her car? -I bought the car.
[DiMango] You bought the car. What kind of car did you buy her?
Uh, it was a Audi.
[DiMango] You buy her an Audi.
I mean, there's gotta be some kind of level of criminal stupidity
that you live in because it's beyond what somebody would do.
By the way, what's your educational background?
Uh, so, I graduated high school.
I worked after high school. I worked, uh, logging.
I ran a cutter. And then in 1999...
Didn't you go into the service?
I joined the Marine Corps. Eight years military policeman.
Uh, 14 years army infantry.
So, you like being told what to do and beaten up.
Because she tells you she can't stand you, she doesn't want to be with you.
You can't come into the apartment. Please give me money.
She says to you, my mother needs $450
because I pay my mother rent.
This is where you don't give her the money, right?
On that day, February fourth, which is the day after I sent her money.
Um, I deal with severe depression and anxiety
that I'm being seen through the VA. I'm 100% VA disabled.
[DiMango] Yeah, yeah. And you're letting this...
You're letting her take advantage of you.
Instead of helping yourself get better.
Instead of using your money to do things
to make you happy, to do things for you.
You're giving it to this...
You're just giving her money! Up to $20,000 in four months.
I'm depressed just reading the case.
[dramatic music playing]
[narrator] Coming up on Tribunal Justice...
Not that he came to see you, but I think you came to show him you,
and that he will continue to give you money.
-No. -[DiMango] Yeah. You know what?
-This is you, right? -[Isabella] Yes, it is.
And what are you doing here?
[theme music playing]
[narrator] James Pritchard is suing ex-sugar baby Isabella Ashcraft
for a $600 loan she used to pay rent.
He says he's tired of Isabella's deceitful behavior
and now wants to teach her a lesson.
Isabella says James showered her with gifts and a car,
but his constant harassment ended their relationship,
and he's only suing to see her again.
Here, this is her. "I don't know what I'm going to do.
Mom said she needs the rent money today.
I literally only have $100."
You, trying to take a position,
"I'm sorry you're going through this."
"Just wish I could get some help."
She plays you like a fiddle. That's how she plays you.
And you go, "Well, Izzie, you've made it clear
that I'm not worth your time or effort." This is what she's done.
I mean, how much could a person be depressed and feel low,
then another person who's just a user and a taker and a loser
says to you, you're not good enough for me to even steal your money from you.
You want to see her, that's all about you want to see her.
You want to talk to her.
Oh, heh, I love this.
You say to him, "I have no money for a... Uber.
I can't fix my... car because you're," meaning him,
"you're so... worried about your dumb ass money."
You say, "I'm in Orlando. I had to take a vacation.
I'll talk to you when I get back."
And you know what you say?
"Had to take a vacation, huh?
When you're worried about the money I owe you?"
-Yes. -[DiMango] You thought it was unfair
-that he took a vacation? -No.
Yes, you did. Well, what does that mean?
Just felt like he just wanted to see me here.
That's... it's $600.
When he could've tried for anything else, he tried for $600.
I think you came here, not that he came to see you,
well, I think he did too,
but I think you came to show him you.
And that he will continue to give you money.
-No. -[DiMango] Yeah. You know what?
-This is you, right? -[Isabella] Yes, it is.
And what are you doing here? Putting yourself out there.
"Someone who can take care of me if needed.
Someone who can maintain my car."
Who are you talking to there?
I actually had somebody ask me what I was looking for in a man.
[DiMango] Just money.
There's something on page 19 in one of the messages
that kinda sums things up.
You saying to her, "You always come back for more money.
Did you ever love me?"
Now, I'm gonna just ask you that question.
Do you think this woman loves anybody?
No, Your Honor.
And you know what you say? "I just wanna move forward in life."
And then, he says to you,
"That's what I thought. It was just about money for you."
And you know what I wrote at the end of those text messages?
"Hallelujah."
When you see this again, you gotta run away.
That's not a relationship. Judge Levy.
Ooph, all right. Well...
It's funny how we can see things differently.
Listen, no one put a gun to your head.
You're an adult. You were looking for someone
that was putting themselves out there on a website,
that you know was looking for a relationship
where you would provide things and they would accept those things.
-Right? -Yes, Your Honor.
But then, there came a time
when you were hoping to develop into something more exclusive.
More real.
Yes, Your Honor. And that was...
-It started about the first of September. -[Levy] September.
Uh, when we basically became more of a couple.
I get... Well, in your mind's eye,
-you became more of a couple. -Yeah.
-That's what you were led to believe. -Yes, Your Honor.
So, when you set up the Defendant into this townhouse,
at a time when you think something's developing,
and she won't allow you to have a key to the place,
you know, you're kind of "bells are going off."
But you were still hopeful.
Yes, Your Honor, I was.
I know, from the messages. Now, Ms. Ashcraft,
-how old are you? -I'm 20.
[Levy] Yeah, you're a baby.
But you're starting off on the wrong foot.
You said to Judge DiMango that you're only here
because he wants to see you again.
Yes. I feel as if that's what it is.
Let me drop somethin' on ya.
The reason that you're here is because you didn't pay him back 600 bucks.
You knew you were gonna come in here,
and the chance of you getting a tongue-lashing from someone
-were pretty good. -[Isabella] Yeah.
[Levy] You think that was a good choice?
-No. -[Levy] No.
What you say online, the photographs you put online,
-all that stuff is forever. -[Isabella] Yeah.
[Levy] But you're 20, and you're not looking forever.
You're not looking how it's gonna affect you.
You were just lucky that the person that you had here
that you were dealing with was, you know, was an honorable man.
Honorably discharged after 22 years?
-Yes, Your Honor. -[Levy] Yeah.
There are some people out there on these websites,
while maybe you haven't come across them,
they don't do nice things to women that they find on these websites.
Yeah, I know.
[Levy] What do you like to do?
What do you think you're good at? Where do you see yourself in ten years?
[dramatic music playing]
[narrator] Coming up on Tribunal Justice...
Sir, when was the last time you sent her money?
February 3rd. That was the $600.
-[Acker] That was the $600 transaction. -Yes. Yes, Your Honor.
When was the last time he sent you money?
-This morning. -[Acker] This morning?
[theme music playing]
[narrator] James Pritchard wants Isabella Ashcraft
to pay back $600 he loaned her for rent.
He says, after spending thousands on her,
she took advantage of him.
But Isabella says, James agreed to be her Sugar Daddy.
Then, his harassing behavior was too much, so she moved on.
And James is only suing because he wants to see her again.
What do you like to do? What do you think you're good at?
Where do you see yourself in ten years?
I want to...
I want to have some kind of office job.
[Levy] You want to have an office job. Okay.
What could you do now that could make that more likely for you?
-You gotta think about those things. -I know.
Because if not, you're gonna look in a mirror in 30 years
and you are not gonna be happy with what you see.
I'm only giving you this sort of lecture right now
because to me, there's not much of a case here.
Because as Judge DiMango indicated,
you spent upwards of $20,000 on cars and rent, and all that stuff.
My bad. You know it. That was all on you.
No expectation of getting paid. But on February 2nd,
ma'am, you made it very clear. This is your text;
"Can I please borrow $600 from you
and I pay you back as soon as I get paid.
I promise to pay you back."
-That was your text. -Yes.
[Levy] And that's what changes everything.
And you could've avoided all of this by just paying him $600.
So, why didn't you?
When I got paid, I had to pay my, um, power bill.
It was off. I didn't have any money left over.
[Levy] And Mom couldn't help out?
-[Isabella] No. -[Levy] Sell the car?
I'd have no way to work.
I get it. But this website and others that you may or may not be involved in,
is no place that you're gonna want to be 30 years from now.
-No, it's not. -[Levy] Get on a right path.
Thank you. Judge Acker.
Are you in school?
I'm not. I work full time at a restaurant.
[Acker] You know, you have to do something else.
There are people who go to night school.
-Yeah. -They have online schools.
You know. So, just make better choices going forward.
You're just too young. You don't need to be stuck in this kind of rut.
No, I don't.
I had a really similar reaction to Judge Levy.
Because it doesn't strike me that you really have a defense here.
I mean, in your answer, you said some things
about him becoming threatening and the like,
but I didn't really see that in the text messages.
Were there any incidents that took place?
That caused you to feel negatively toward him?
I looked out my roommate's window one night at 12:00,
just randomly, I see him walking away from the door.
Like back to his truck.
[Acker] He was checking on you.
No, he told me he was sleeping at 8:00.
Four hours later, he was trying to come into the house.
With just me there.
[Acker] Sir, when was the last time you sent her money?
Uh, that would be February 3rd.
After the $600 transaction?
No, that was the $600.
-[Acker] That was the $600 transaction. -Yes. Yes, Your Honor.
When was the last time he sent you money?
This morning.
[Acker] This morning?
-Can I show you the text? -[Acker] Sure.
Please tell me no.
It's just that top page.
From the Plaintiff,
"Put all this stuff going on aside.
Have you eaten since getting here? I know it's expensive."
-You sent her that this morning? -Yes, Your Honor.
Before you showed up in court?
-Yes, Your Honor. -[Acker] And her response was, "Barely."
And then, you said to her again, "Go get breakfast
and tell me how much to send you."
And you said, "Okay." So you sent her money for breakfast?
Yes, Your Honor.
Dude, you can really do better than trying to buy a woman's affections.
You really can.
You have to make better choices too.
Yes, Your Honor.
Are you gonna like, try to buy her dinner tonight?
-He's like, yes. Okay. -Yeah.
-Was that a yes? -[James] Yes, Your Honor.
Oh, my God. We're not done with therapy yet.
-We're not done with... -[laughter]
[DiMango] The rest of this here. She tells you...
You say, "Get breakfast, tell me how much to send you." "Okay."
"Get some extra to take to the room for lunch." "Okay."
"I spent over a hundred last night at a steak house.
Great steak, but not for that price."
"Thank you." "You're welcome."
"No strings attached. I will take you later."
"You should at least be able to enjoy your first trip."
You know, what bothers me is
that I really, really, really thought that there was hope for you.
Yes, Your Honor.
[DiMango] But you know what, there isn't.
What are you expecting to happen here now?
I'm just expecting to get my money back and move forward.
[DiMango] Move forward? But you're gonna take her to dinner.
Where are you moving forward to? She's not your friend.
You think this woman's your friend? Look at the expression on her.
She's got a smirk on her face. This woman is not your friend.
-I understand. Yes, Your Honor. -No, you don't. No, you don't.
I've gotta get off the bench.
If my colleagues have questions, I'll stay. I don't wanna be here with you.
Just hold on. Don't get up so fast. Wait a second. Give me a minute.
I'm giving you the time, I just don't want to be here.
You know, Ms. Ashcraft, you seemed pretty happy
when Judge Acker asked you when the last time he gave you money was
that you were just real happy to say this morning.
But that was right after you almost got into tears
because of an incident in which you described yourself as feeling unsafe
-and threatened. You know where I'm going. -That part.
I prosecuted domestic violence cases. Cases in which women
were murdered viciously, violently because they made bad choices
and put themselves in positions that they knew were unsafe.
I'd never give someone a right to put their hands on you.
But you just told Judge Acker that there was something about him
and the way he felt about you that made you feel unsafe.
-Right? -Right.
-[Levy] You're not gonna smile right now. -Right.
-[Levy] You just answer my questions. -Yes, Your Honor.
And in your answer, you wrote about stuff where you said
that he was gettin' kinda aggressive
'cause he felt hurt, betrayed, taken advantage of. Right?
-Right. -[Levy] And he left you some messages,
some voice mail messages that really got you worried in October.
-And you were scared, right? -Right.
Mind you, I'm not saying that you were an ax-murderer.
-Yes, Your Honor. -[Levy] That's not the point of this.
The point of it is, your gut was telling you that you were unsafe,
and that you had to get someplace safe.
-Right. -[Levy] And for a $20 breakfast,
you're prepared to put yourself right back in that same situation.
-Stop. -I'm not.
-[Levy] Stop. Yeah. -I'm not putting myself in that position.
-I hope not, Ms. Ashcraft. -I'm not.
If you've seen photographs of crime scenes like I've seen
with women just your age...
Mm-mm, it would keep you up at night.
-You gotta do better. -I am.
[Levy] All right.
We're gonna retire to deliberate. Thank you both.
Court is now in recess. Parties will be recalled.
[dramatic music playing]
Some people are hopeless.
I could be one of them because I keep trying to convince people
that what they're doing is people are taking advantage of them.
Listen, no matter what she did before, this was clearly, can I borrow $600?
I promise to pay you back. You know, like I always say,
when Wimpy said to Popeye,
I'll gladly pay you Tuesday for a hamburger today.
I mean, this is what it is. She owes him the $600.
And he really should take it and go directly to intensive counseling.
They're both very troubled people to live this kind of life
where one just takes and takes and the other just gives
without any regard for his own self.
And he keeps telling her in the texts if you recall,
I'm gonna help you find Jesus, I'll help you find God,
I'll help you find this. And all she did was find her way back to him, so.
And him back to her.
Yeah. I mean, he wanted to be here to see her,
and she wanted to be here to get lunch and dinner.
Yeah. Listen, I agree. I said everything I had to outside.
I hope that she changes because that road ahead for her
does not look pretty. Again, she was lucky with him.
And I just hope that she realizes that
and finds something else to do with her time.
I think that there's a real sadness to both of them.
I think that she sees her options as more limited than they may be.
You know, she's young enough to have a new path.
And I feel bad that he doesn't feel that he can do better than this
and that he had to keep getting wound up in this situation.
There's something very sad about the whole case,
but the legal issues couldn't be clearer.
I know. All right, so, we're unanimous.
He's gonna get the $600 back.
[dramatic music playing]
Court is back in session.
Both parties are reminded that you're still under oath.
-[DiMango] Thank you. -[Britt] You're welcome.
[DiMango] Well, we've reached a unanimous decision.
There was a promise to repay a debt. It was a loan. You said it was.
You promised to repay repeatedly. And she owes you the $600.
Where the three of us really were somewhat different was
on our views of both of you.
But I think we all came down to one point,
which is that both of you are troubled.
Both of you need some sort of help.
Both of you keep shaking your head yes to everything
because you're both pathological on some level.
That's my view; they didn't say that.
And it's very sad. I mean, it's very sad that you're gonna get $600,
and you're gonna walk out this door, and you're gonna buy her dinner
and take her shopping.
The rest of that text was I'd love to take you shopping.
The part that angers me in all of this is how you could think so little of yourself
that you would go through all of this, only to do it again.
So, when you do that, and you take that 600
and you give it all back in some way,
she's right, this was all about coming in here to see her.
And though my colleagues each feel a sense of hope
that there's something that's gonna make you both better,
honestly, I don't feel any chance that you're gonna get any better,
and you're gonna do anything better with your life.
But as I said, we all agree
that you're entitled to the $600 unanimously.
And I should've walked off the bench before.
That's how I felt because you're just gonna spend it on her.
-[gavel bangs] -[chuckles]
This case has concluded. All parties are excused.
[triumphant music playing]
He wants $600 but just sent me money this morning.
All she has to do is hit block.
I... I don't know.
You can't treat somebody like I was treated.
He bought my car because I didn't talk to him for a month.
And he told me that I needed a car.
And I made a lot of mistakes. And I admitted to her all my mistakes.
I don't think I should have dinner with him, but I'm not sure.
No dinner reservations. Probably not.
Maybe.
I want to enjoy being single.
Probably not.
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[theme music playing]