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Raising Independent Children

from How Not to Screw Up Your Kids

39m 48s

Raising Independent Children

This episode of Legally Brunette examines the death of Jenny Lupton, a 50-year-old Southwest Airlines flight attendant found dead outside the Hilton Hawaiian Village in Waikiki on August 20. Authorities initially suggested she jumped from her 24th-floor balcony, but her family and friends strongly dispute that conclusion. Jenny had spent nearly three decades as a flight attendant and was a devoted mother to her 15-year-old son, Caleb, whom she called her whole world. Friends Angela and Jen describe her as someone who always showed up, loved being the life of the party, and was open about her struggles, yet was in a positive place before the trip. They say she had been dancing and getting a tattoo only hours earlier. The family has received little information from investigators, including no key card records, no 911 details, no autopsy results, and no findings from her devices. The hotel tower reportedly lacks security cameras on guest floors, and anyone can access upper floors without a key card. Jenny was a Cherokee Nation member, and her family hopes the Savannah's Act and tribal involvement will force a more thorough investigation. Friends suspect foul play and believe public attention may help uncover what really happened.

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Speaker 1Hi, guys. Welcome to Legally Brunette. I will be your host today, Emily Simpson and. Shane. All right. Today, we are going to talk about a case that we talked about previously, which was about a Southwest Airlines flight attendant who was found dead outside of one of the biggest resorts in Waikiki. This happened back on the morning. It was the morning of August 20th. Do you remember this conversation? It had very suspicious circumstances as far as her death. Yes. Okay. She was on a layover in Honolulu, and she was just 50 years old. By the way, I would just like to reiterate how young 50 is, just for everyone out there. Just very young.
Speaker 6I think more for yourself.
Speaker 1She had spent nearly three decades as a flight attendant, had a teenage son back home in Oklahoma, who she called her whole world, and only hours earlier had been out dancing with a friend and also was getting a new tattoo. Her name was Jenny Lupton. Authorities have said that Jenny jumped from the balcony of her 24th floor room at the Hilton Hawaiian Village. Her family does not accept that as the whole story. They've said publicly that they don't believe that Jenny would have harmed herself and that the timeline does not add up. And they've asked Oklahoma's attorney general to help push for a thorough investigation. In Honolulu, police say their homicide detectives are investigating and they've reached no conclusion about how she died. You've probably seen the headlines, but headlines can't tell you who Jenny truly was, what her life looked like in the days and weeks before that trip, or which questions her loved ones are still waiting on. Today on Legally Brunette, we have two of Jenny's closest friends. Their names are Angela and Jen, and they are going to join the podcast. They knew her long before her name was named, and they're here to talk about the Jenny that they knew, what they've learned since that morning, and the parts of this story that just are not making it into the media coverage. This is an open investigation, so it's ongoing, and we'll be careful to separate what's confirmed from what is still unknown. But we are going to welcome her friends, Angela and Jen, onto the podcast today. Hi, Angela. Hi, Jen. How are you guys? Good. How are you? I'm good. Thank you so much for being on Legally Brunette. Just to let you know, we covered this case a few weeks ago because it was in the media, and it was interesting, and obviously we do true crime, so we were talking about it. And I'm excited to have you guys on here today because, first of all, before we ever get into crime and talk about the investigation or facts or whatever, I think it's really important to talk about who Jenny was, and you guys were two of her closest friends. Do you want to just remind everyone about Jenny, who she was, what she was about? Just give us some details about her.
Speaker 7Yeah, Jenny was, gosh, we've both been friends with her since high school, and she was somebody that always showed up. No matter what it was, what you were celebrating, big or small, she was there. And you also always knew whatever you were doing, it was going to be fun. And she was an amazing mom to her son, Caleb, who is 15 years old. She loved being a flight attendant, and she was always the life of the party and just so full of life and energy.
Speaker 8All that. Answered the phone on the first ring, like literally someone that would always pick up.
Speaker 1That's nice. How has, now I know she worked for Southwest for 30 years, which is really commendable. People don't really work for companies, the same companies, for that long of a period of time, which is a testament to her work ethic and her integrity. And things like that. How has Southwest been involved at all? Have they reached out to the family? Do they reach out to her son? What have they done?
Speaker 7Yeah, so they were really helpful getting Jenny home and were really great to the family. They celebrated her from the moment she left Honolulu to, you know, when the family arrived in Phoenix and they changed planes. And then there was a tarmac full of people here in Oklahoma City, when she arrived home, they've, you know, they paid for several family members to go and bring her home and they've checked in. And, you know, they've been, they've been good. They've been good to the family. And they've been, it was nice seeing so, like seeing so many of her colleagues that she, you know, had an impact on show up for her, not only in Oklahoma City, but some of them came to Phoenix as well to celebrate her when she was there. So. So it's, and then the funeral, so many, they all turned out in their uniforms. It was really great. So they've been good to the family and, you know, stayed in touch and are helping with what they can, but, you know, there's only so much they can do too.
Speaker 1Right. Now, I believe the police are claiming that this was a suicide, even though the investigation is ongoing. I believe that's their initial takeaway, their initial thoughts that this is a suicide. Were you having conversations with her around this time? Do you recall her state of mind or, or anything that would, that would indicate that she was depressed or upset or was having a hard time during this time period? None of that.
Speaker 7Yeah, none of that. She was, you know, I mean, I think both Jennifer and I have seen Jenny in some pretty dark places over the years, you know, I mean, she's had, you know, trials and tribulations like we all have, but this was not one of those times. She was doing great. Caleb was doing great. You know, work was going well. Um, everything was on the up and I just, you'll never get me to believe that this was self-inflicted.
Speaker 8She just had so much that she was looking forward to. Like Caleb was playing football on the same team as her nephew for the first time. And high school football in Oklahoma is a very big deal. And she was looking forward to all of it. It just, it just doesn't add up at all.
Speaker 6You had mentioned that she had a challenging times. Does that mean she opened up? Did she open up to you when she, when times were difficult?
Speaker 8She's an open book. Like she would always tell you everything, even if you didn't want to know, Jenny was going to tell you the good, the bad, the ugly. Um, and she just wasn't in that place in her life at all.
Speaker 6Which makes it a little bit more concerning that it was self-inflicted or that's claimed to be self-inflicted if she was such an open book to you. Right. So it was a surprise.
Speaker 7Yeah. We've learned nothing that, you know, since. She's passed that not, you know, a handful of us, you know, already knew about. I mean, she was somebody that I always admired it about her because she was always so vocal about her struggles and everything she was going through. She never, she always felt like everything was going to work out, you know, and she never let anything make her feel shame or, you know, she never really internalized it. She always, she was very good about talking it out, reaching out for help.
Speaker 1Now, I just have to ask this. I know she has one child. She has a 15 year old son. Um, I have two sons. And I'm extremely close with them. And I feel like they're the light of my life. So I can't fathom that someone, even let's say hypothetically, she did decide to, to take her life for some reason that night. Don't you feel as if there would have been some type of, of, of reach out to her son, some type of text, some type of letter, something that she would have communicated with him if that were the case?
Speaker 7I, I do. I personally do. I think that, um, I mean, she would just never leave him. I mean, she just never would. I mean, I also have boys, I have twin boys. And, you know, especially like being a single mom, I mean, you just would never, I mean, they're your whole world, you know, and you don't, you would never want to do anything to leave them, you know, and that's actually one of my biggest fears is to, you know, leave them. And I know she felt the same way. And, but I really do feel like, I mean, Jenny was always very big on her correspondence. I feel like if there was anything like that going on, you know, she would have somehow found a way to communicate it to somebody. But I honestly just don't, that would just never be the answer for her.
Speaker 8I mean, the thought of her leaving a note or has never even crossed my mind, because in my mind, there's no way she would have done this.
Speaker 1So you can't even go there. So your mind doesn't even go to, I can't believe she wouldn't even leave a note or communicate something because you're saying there's just no way that this was self-inflicted.
Speaker 8No way. Not at all.
Speaker 1Do you, either one of you, can you explain? Um, the layout of the hotel, I do believe she had stayed there numerous times. Is that somewhere where flight attendants stay when they're flying in and out of that hub? Is that, you know, where pilots and flight attendants go to stay and what, what is the layout like as far as the dumpster, the way she landed? What is your takeaway from that?
Speaker 7So the Hilton Hawaiian village, it's, you know, basically there's various towers you can stay in and I've never been there, but I've seen the pictures and the family. Described it to me, but, um, she was in and, you know, and I always thought of it cause they call it a resort. I always thought of it as being like, you know, you go into gates and here's all these towers and you, you know, you're just restricted to the people that are staying on the resort, but that's not how it is. It's more of like just kind of disjointed hotels, you know, it almost was like separate hotels. And so the hotel, the tower she was staying in was the Kalia and it's, you know, sort of tall, narrow with inserts on the side and the side where her room was on is where the dumpster was below, but it's almost, and I, you know, it's, when you look at it in pictures, it is very hard to determine or understand or comprehend that she could have fallen in the way that they said she fell, um, just the placement of a room, um, the, you know, just the trajectory that they're trying to say that it happened, or at least that they were initially saying it happened. And the way she would have had to, you know, the little tiny opening she would have had to have fallen through to land into a dumpster. It just, none of it really makes sense to me. Um, and you know, I, yeah, I, it's a very, and another thing that's very concerning too is, you know, anybody can get up into that tower. You don't need a key card. I mean, you can get up into those floors without a key card. You, when you go up and the family was on her floor, there's no cameras. Um, the only cameras they found were in the main elevator, um, like the main elevator bank in the lobby. So, you know, I don't, I don't really, I mean, to me, that is very concerning, you know, because it feels like in that area, you should probably have a little bit more security in
Speaker 1cameras. Yeah. So that was one of my questions I was going to ask you as far as the investigation was concerned. I was going to ask, is there surveillance video of, of her floor or the elevators on her floor? So you're saying that there's none of that, that the only way. They're the only place that there's surveillance video is on the lobby floor.
Speaker 7Wow. Yeah. So for what the family could tell and, you know, and we obviously had, you know, people on socials commenting and saying, you know, we've stayed there. There's no cameras on that floor. There's no cameras on that elevator, you know, in that tower, it's kind of like one of the older towers, you know, so it's not as updated as some of the others, which I think probably have a little bit more security. Um, but yeah, so they, you know, so when the family went, they specifically, you know, went into that tower without, you know, they were in a different tower anyways, but they went there, um, and we're able to go up without a key card and then walked along the hallway and we're videoing, you know, to see if they could see any cameras and they didn't see any at all. Um, and then, and you had mentioned, uh, you had asked earlier about the flight attendants. They Southwest usually puts them there, the Hilton wine village or the. So there's two different hotels. They usually stay out in that area.
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Speaker 1What about as far as the investigation is? I'm just thinking because I've done so much true crime. Obviously, there's the forensics of. Her cell phone. There's I don't know if she wore an Apple watch, but you can always tell if someone went upstairs or went downstairs if their heart rate goes up or their heart rate goes down. Do you know anything about that as far as if she was communicating with anyone that night? Was she meeting someone? Do you know anything? Or is that hush-hush on this investigation?
Speaker 7It's apparently hush-hush. They still have her devices. And I know when the family went to Hawaii. To bring Jenny home, they met with the detectives and the detectives still at that point had not gone through her phone or any of her devices. So they were hoping that's been done now, but they won't even like let the family know if it's been done or anything about it. So we're hopeful that they because she had an iPad and an Apple watch and also her phone.
Speaker 1So we're hopeful that there's something on there that will give them a clue as to who she was communicating with. If there was anyone, if she was meeting anyone, obviously we would know from the cell phone. But you're saying there's no. There's been nothing divulged as far as what's been found on her phone from that evening. Correct. Yeah. Are you a little suspicious of the hotel as far as not having security footage? Do you think they're trying to protect themselves or what's your thoughts on that?
Speaker 7You know, I don't it's hard to to say because, you know, it's because we've been given such little information. But I do know that. You know, whatever surveillance footage there was, was not handed over freely that had to be retrieved, you know, that had to be subpoenaed by HPD to get it. And I don't know if that's standard, you know, if that's typical, typical process. But it did really feel like initially, at least to the family that, you know, the Hilton Wine Village was kind of driving the narrative and the investigation. And that could have been, you know, one of two reasons, because the day that they found out was also. Hawaii Day. It's like state the state day or something. So a lot of the offices were closed. You know, the state offices were closed. And so they initially spoke to the head of security at the Hilton Wine Village. And so it really felt like that's where they got a bunch of information from that really, you know, gave him the impression that this was being considered or treated like a suicide. Now, who found her?
Speaker 1Who initially found her body?
Speaker 7So from what we've seen, were told it was one of it was it was like a grounds worker. It was basically somebody that was working in that area. That dumpster that she fell into, it's not like a normal trash dumpster. It's for like, foliage and leaves. And you know, when they're doing cleanup around. And so somebody that was in that area is the one that discovered her.
Speaker 1You know, there's been another mysterious death on that same island. So there was 51 year old Shannon Bartholomew was also found in a canal was found in a canal. And you've been in contact with her family. Do you believe that there's similarities between the two deaths? What has it been like to speak to that family?
Speaker 7So it's actually Elizabeth Nolan's family that we were she was another one to you. There's been several.
Speaker 1So there's more besides the Shannon Bartholomew. There's an Elizabeth Nolan. Is that what you said?
Speaker 7And another named Brianna Charlie to that. Okay, her family, but Elizabeth Nolan, she was the most recent. So she her. She died in 2025. Similar situation found in a trash, like a dumpster, but it was for, you know, through a trash chute, basically. And the family felt like, or at least hoped that law enforcement was going to be doing their job and, you know, investigating this properly, that come to find out, there wasn't really much of an investigation done once they got the police reports and had, you know, they identified the cause of death, the death certificate was updated, or the autopsy report was updated by 8am the next day saying it was suicide. And prior to doing any kind of investigative work.
Speaker 1Wow. I do I read here that so Jenny's family did ask for a full autopsy and a rape kit to be done, but there was pushback. See, that makes no sense to me. I feel like that would be standard in any investigation that when you find someone in a dumpster, that those would be standard type of investigating that you would do immediately to figure out if there's any foul play, if there had been some type of sexual activity, if there was a rape that occurred, but that do you know, if those are have happened, or they're just pushing back on that?
Speaker 7They did do them, but it did take quite a bit of asking and demanding from the family. But I guess that's all I mean, nothing, they've given us no, you know, results of her autopsy at all. And said the toxicology obviously takes, you know, can take like, four to eight weeks or something. So that, but honestly, you know, we're not even sure how much information we'll get from that, you know, if they're keeping the rest of the investigation, you know, hush hush. So I don't know.
Speaker 1So do you know, so there were you don't know if there was any results from a rape kit as well. So nothing, the family doesn't have any information on that, as well. No. Angela, you've mentioned that Jenny was part of Cherokee Nation and Savannah's Act as a bipartisan effort to improve the federal response to missing or murdered indigenous persons. How are you hoping this act helps your effort and investigating Jenny's death properly? Have they, have they gotten involved in this investigation at all?
Speaker 7And so Teresa has reached out, Jenny's sister has reached out to the tribe and, you know, filed the appropriate paperwork and is, has been talking to them. And what we're hopeful is that, you know, the Cherokee Nation will, they're either attorney general or, you know, their investigative team will then be able to, you know, have some sort of open communication because of this law with the Honolulu PD, you know, to ensure that it's being properly handled. And, you know, initially, we really felt like they were treating this as a suicide. And quite honestly, until our, our attorney general called and, you know, let them know that he had eyes on this as well. Our attorney general here in Oklahoma called their attorney general. And I don't, I don't know that they were going to treat it any other way. So it really took that. And we feel like that if there's not more involvement and more eyes on the investigation as it goes, then, you know, it could end up being the same throughout.
Speaker 1Now, what do you think actually happened that night? Do you think that she actually did fall from the balcony and land in the dumpster or do you think something happened to her and then she was placed into the dumpster?
Speaker 7You know, I go back and forth. I mean, I feel like, you know, sometimes I look at the pictures and I think, goodness, you know, it really appears to me like somebody did this to her, maybe threw her in from a, from the pool deck or, you know, there's just so many other areas that looks like it would be easier or more logical that she was laying in that dumpster. Um, but then, you know, I, I go back to, to the fact that she was also found in the same clothes that she had on the night before. Um, I mean, you know, we get back, we're back to our room for the night. We're changing clothes. We're not keeping on our uncomfortable jean shorts and our tight
Speaker 1shirt. You know what I mean? Like, Right. That's exactly when you said that, that's what I was thinking. The minute I walked through the door, I'm like the bra is unhooked. The, you know, the dress is off, the heels are off.
Speaker 7Absolutely. First thing we do. Mm-hmm. And, you know, so she was, she had that same outfit on because she was either leaving again or someone was coming to her room, you know, that's, and so there's so many different possibilities. Um, one thing that they did tell the family is that the furniture on the balcony, um, was in the place when they went to her room, you know, and, and investigated the furniture on the balcony was in the place where it always is. It was not moved. So to me, that is an indication right there that this can be self-inflicted. I mean, she was five, two, how is she doing this? You know, if she's not got something pushed up against that railing to climb over. Um, but you know, they, they also said that it appeared to them that her bed was not slept in. So, or I, the words they used were, was untouched. So what is she doing in there? If they didn't find her until 5:30 in the morning and that's around the time they think it happened, she wasn't just standing in her room for, you know, enough.
Speaker 1Yeah, you're right. That doesn't make any sense. She obviously wasn't just dancing around in her, you know, in her room all night, you would have laid down on the bed. You would have thrown the pillows off at least, or, or put the covers over you.
Speaker 8And the chances would actually land in the dumpster, whether somebody threw you or you John are so small. I mean, like it's almost impossible that that would happen from the 24th floor.
Speaker 1Yeah. I was thinking that too, that the likelihood of her going over and landing in it is crazy, virtually impossible. So then do you believe that it happened somewhere else and that not from her room? Like she was something happened to her while she was out and then she was put into the dumpster.
Speaker 8In my mind, I visualize that. That's why I would love to see footage of her getting, did she get on the elevator to go up to her room ever? Did she make it to her room that night at all? Did, did anyone use the key card to go in, you know, any of that, but we don't have any of that data, right?
Speaker 1Because we, we've talked about several cases, even on like the cruise ships where they know who goes in and out, because you have a key card that lets you in and out, they have a whole log as to the exact times that people enter and exit. So has that information not even been given to the family as far as when her key card was used to go in and out?
Speaker 7Yeah, no, they've given us absolutely nothing. Um, and you know, and we're not sure if that's the standard, you know, or if that is, um, something that, you know, we should at least be giving, be given a high level, you know, of information, like just a, they don't even know, you know, we were talking the other day about what time was 911 called, you know, what, what was that called? What was said? What time did, you know, first responders arrive? What time did the medical examiner arrive? And they, they wouldn't give them any of that either. That seems like pretty basic information, you know? Um, I don't know personally how that would impede an investigation if it were told. So it just feels very, um, you know, they did her autopsy on August 25th. So, um, I believe that, yeah, it was the Tuesday, the following week. And during that autopsy, they gave the Honolulu PD their, um, Jenny's code to her phone cause her son had it. And the family was not there until, um, let's see, we, she came back to Oklahoma city on the 10th. So it was the ninth when they met with Honolulu PD, the detectives, and they still hadn't been in, in her phone, but they had her passcode that entire time. Like to me, I don't know, I'm, you know, not law enforcement, but I feel like that's one of the places you start, you know, especially when somebody is alone or it's an unattended death, whatever that means, you know, but it, um, it just didn't give me a whole lot of reassurance that this is being handled properly. :
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Speaker 9Gain confidence. I'm Hamza. And I'm Martin. It's a podcast. I know there's a lot of them going around. But why should you listen to ours? Well, we're only the best podcast in the entire world. And we talk about pretty much everything under the sun. For example, music we're listening to. Underground music. Trending music. Drama in music worlds. Yes, sometimes we even talk about just everyday mundane situations in our lives. Like the cool Uber driver we just had. Or the food we just ate that was surprisingly delicious. Or we'll talk about the Met Gala and the looks that they wore. Are they awesome? Are they trendy? Come find out. Because our opinion matters. And so does yours. And this is a place where all of our minds can come together and connect. So what are you waiting for? Come connect with us. On the iHeartRadio app, Apple Pods, or wherever you get your podcasts.
Speaker 5So as far as her autopsy, was the final report from
Speaker 1the medical examiner, does it say officially suicide? Or is there just no determination at this point?
Speaker 7It says pending.
Speaker 1Pending. Okay. Well, the question is, is there really an investigation going on? And I don't know. My takeaway from the conversation with you and the little bit that we talked about before when we talked about this case previously is, is this a problem? Like, because we're talking about a high tourist area, we're talking about a hotel, we're talking about Hawaii.
Speaker 6That was going to be my question, was just like the movie Jaws. You know, they didn't want to alarm anyone that Jaws was around, right? Because it's the Fourth of July weekend. They don't want to disrupt the tour. This is a big, important thing for our island. I didn't know if Hawaii kind of has the same thing. Hey, we don't want to run around and say that people are getting thrown off buildings or murdered or whatever. And then they stop coming.
Speaker 1Right. I mean, that would be my takeaway is that a lot of this information isn't given and isn't out there publicly. And just because they want to downplay that there's anything going on wrong in this area, they want the tourists to continue to come. And if you hear about. A death of a young woman, a single mom.
Speaker 6Possibly repeated deaths.
Speaker 1Repeated deaths, then you're not going to want to go to this destination.
Speaker 7Correct. Yeah. I've had that feeling as well, just based on some of these other cases we've heard about that, you know, I mean, for instance, you know, the one that I mentioned a second ago, Elizabeth Nolan, you know, she, 72 years old, found nude in a dumpster that she would have had to have crawled up into a trash chute, sent herself down. The trash chute to then end her life in this dumpster. Completely nude. So she would have had to walk down the condo hallway, you know.
Speaker 1And this was ruled a suicide?
Speaker 7Suicide. And she was there. She would. And she had just, you know, purchased a very expensive, like, Hermes dress that her daughters were telling us about that she, you know, planned to go to this birthday party, like, in a few days. And she would stay in. She was from Canada, but she would stay in Hawaii for, like, six months out of the year. It was, like, her favorite place. And she was there with her fiancé. He wasn't investigated, according to her daughters. He was just. His word was taken, you know, and they moved along. Isn't that the first place you look? I mean, isn't that very suspicious that, you know, you're there with a fiancé that, you know, was the last person to see you live, but he just gets to tell you the narrative and you believe it? To me, it just doesn't feel.
Speaker 1Well, none of that makes sense. I don't know. I mean, I don't know a lot about suicide statistics, but I don't really feel like people get naked. I don't even get in dumpsters when they commit suicide.
Speaker 8No, not. I mean, no. Me either. I'm like, that doesn't even seem
Speaker 1like a sure way to do it. Like, who would do that? I don't know. That just seems like. That just screams foul play to me. And why there wasn't more of an investigation doesn't make any sense at all. So, it's so common that online sleuths solve crimes or at least find information that others may have missed. Do you guys have hope that just talking about it and putting this information out there can help bring light to your case and help solve your case? Of this alleged crime?
Speaker 8Yeah. Of course. I mean, it seems like somebody would have maybe seen something, you know? I mean, Jenny had a very recognizable face, like, always smiling, big dimples. Like, she was a memorable person. It just seems like somebody would have had to see something or hear something. I mean, even if she did fall into the dumpster, I'm sure it made some noise, you know? So, just hopefully, we can get just as many people, like, thinking about it. And not forgetting that this is a single mom who is no longer here and was very loved. And just, there's no way she would have done this. We need to figure out what happened.
Speaker 1Exactly. All right. Well, thank you guys so much for joining us today and for talking about Jenny. Obviously, our listeners out there, if anybody's in Hawaii or is familiar with this hotel or knows anyone or has any information about Jenny, please let us know. If you have any information, we would love for you guys to come forward and send me a message on Instagram so that we can help get Jenny's case out there and get the information that the family needs in order to get to the bottom of what really happened to Jenny Lupton. So, thank you both for being her friends and also for joining us today on Legally Brunette. We really appreciate it. Thank you so much for having me. Thank you. Thank you. All right. What are your thoughts on this case? To me, this case just screams foul play.
Speaker 6It doesn't feel like law enforcement is going to do much.
Speaker 1I know. It almost feels like there's just some good old boy standard in Hawaii that it's like when there's something suspicious that happens, we don't want to mess with the tourists and we don't want to mess with the tourist money coming in. So, we can't put out there that there's women getting harmed.
Speaker 6Right. You don't want it to be there's a serial killer on the loose.
Speaker 1Or there's women being harmed.
Speaker 6Right. Like every month, there's a new murder in a hotel of all places, right, where tourists go. Right. So. I don't know.
Speaker 1It just seems to me when you find a woman. In a dumpster. That's suspicious in and of itself. Yeah. Yeah. I mean, even if she did jump, the chances of her landing in the dumpster.
Speaker 6And he said it was 24 stories.
Speaker 1Yes. And are there no witnesses? Did no one see this woman? Did anyone? I mean, people are out and about all times of the night. People are on their balconies. This is a huge hotel. I mean, anytime we just went to the Bahamas and anytime I was out on the balcony, you could see lots of other people on the balcony. There's people below. There's people in the pool. Even if it's late night or early morning, there's always activity and things going on. There's always people around. There's always maintenance and workers and all the things. So I don't understand how something like that. Let's say, for example, for just hypothetically, she did go over the balcony and then she did land in the dumpster. Can you imagine the noise that would have made? I mean, she flew 24.
Speaker 6And then the autopsy report should show a significant amount of body damage.
Speaker 1Right. And it shouldn't just be blunt force trauma to the head. No. It shouldn't be damage.
Speaker 6It should be damage to all the limbs, the torso.
Speaker 1So what is that? What does the autopsy report look like? What does the rape kit look like? Was she did she meet someone? What is that?
Speaker 6You could go up to the 24th floor and chuck a basketball off of there, baseball and still not get it in there.
Speaker 1Probably not. And why is this so much time has gone by and the family doesn't have any answers as far as the medical examination? Where are the injuries? Was it just to the head? Was it to the full body? What is the result of a rape kit? Who was she? Was she meeting that night? There's got to be video surveillance from the bars that she went to. Do we know who she was talking to? Did she talk to some man in the bar? What about the key card going in and out of that
Speaker 6matters if you're trying to sweep it under the rug?
Speaker 1I know, but I want to investigate this crime. I want to take a legally brunette field trip. We can put together an investigative team. Anyone out there interested, we can take a trip to Hawaii. We're going to stay in this hotel. We're going to get the key card in and out entry. I'm going to I'm going to follow around the hotel manager until I get the information that I want. We're going to look at the dumpster. We're going to look at the balcony. We're going to figure it out. All right. We're going to solve this crime. Let me know. All right, guys. Thank you so much for listening to legally brunette. If you know anything about this case, you live in Hawaii, you've heard about it, you've seen anything. Please find me on Instagram and let me know. Jenny Lupton deserves to have a full, thorough investigation as to what happened to her. Her family and her son deserve that. So thank you guys for listening. If you have any information, let me know. As always, please follow Legally Brunette wherever you listen to podcasts. And if you have any other recommendations of cases you would like us to investigate or talk about, please let me know on Instagram. Thank you guys so much for listening. We appreciate you. Guaranteed human.

Podcast Summary

Key Points:

  1. Southwest Airlines flight attendant Jenny Lupton, 50, was found dead outside the Hilton Hawaiian Village in Waikiki on August 20 after reportedly falling from her 24th-floor room.
  2. Honolulu police initially treated the death as a suicide, but the family rejects that conclusion and says the timeline does not add up.
  3. Friends Angela and Jen describe Jenny as a devoted mother to her 15-year-old son Caleb, a 30-year flight attendant, and an open person who was in a positive place before the trip.
  4. The hotel tower where Jenny stayed reportedly has no security cameras on guest floors or elevators, and anyone can access upper floors without a key card.
  5. The family says they have received almost no information from investigators, including key card records, 911 call details, autopsy results, or findings from her phone, iPad, and Apple Watch.
  6. Jenny was a member of the Cherokee Nation, and her family hopes the Savannah's Act and tribal involvement will push for a more thorough investigation.
  7. Similar suspicious deaths of women in Hawaii, including Elizabeth Nolan, were quickly ruled suicides despite what families consider questionable circumstances.
  8. Friends believe the case may involve foul play and hope public attention will surface new information.

Summary:

This episode of Legally Brunette examines the death of Jenny Lupton, a 50-year-old Southwest Airlines flight attendant found dead outside the Hilton Hawaiian Village in Waikiki on August 20. Authorities initially suggested she jumped from her 24th-floor balcony, but her family and friends strongly dispute that conclusion. Jenny had spent nearly three decades as a flight attendant and was a devoted mother to her 15-year-old son, Caleb, whom she called her whole world.

Friends Angela and Jen describe her as someone who always showed up, loved being the life of the party, and was open about her struggles, yet was in a positive place before the trip. They say she had been dancing and getting a tattoo only hours earlier. The family has received little information from investigators, including no key card records, no 911 details, no autopsy results, and no findings from her devices.

The hotel tower reportedly lacks security cameras on guest floors, and anyone can access upper floors without a key card. Jenny was a Cherokee Nation member, and her family hopes the Savannah's Act and tribal involvement will force a more thorough investigation. Friends suspect foul play and believe public attention may help uncover what really happened.

FAQs

Jenny Lupton was a 50-year-old Southwest Airlines flight attendant for nearly three decades and a single mother to her 15-year-old son, Caleb. Friends described her as the life of the party, an open book, and someone who always showed up for the people she loved.

Authorities said Jenny jumped from the balcony of her 24th-floor room at the Hilton Hawaiian Village in Waikiki on the morning of August 20. She was found in a dumpster below, and Honolulu police have not reached a conclusion about how she died.

They say Jenny was in a good place in her life, was excited about her son's upcoming football season, and was always open about her struggles rather than internalizing them. They also point out that she would never have left her son without some form of communication.

Friends said anyone can access the upper floors of the Kalia tower without a key card, and there are no cameras on her floor or its elevator. The only surveillance footage was reportedly in the main lobby elevator bank, and it had to be subpoenaed by police.

The investigation remains open, and the medical examiner's final report is still pending. Police reportedly have not shared autopsy results, rape kit findings, or phone data with the family, and her devices were still not examined when the family met with detectives.

Southwest helped bring Jenny home, paid for several family members to travel, and coordinated a tribute when her body arrived in Phoenix and Oklahoma City. Many colleagues attended her funeral in uniform.

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