king: do you ever fear your own health? my own health? yeah, there are nuts in this country. no. the kennedys must think about it. how could they not think about? it's not something that it's sort of, like, walking around wondering if you're going to be struck by lightning. it's kind of -- it's just not something that you really keep in the forefront of your mind much. but it might affect decision-making, right, going into politics, right? right, but it doesn't. ♪ ♪ hey, everyone. welcome to "how it really happened." i'm hill harper. to many americans, he's simply known as john-john, a nickname created by the press and one that jackie kennedy once admitted he hated. he was the heir to his father's legacy. however, john f. kennedy jr. strove to be his own man, aware of the expectations but set on creating a life of his own making, but that life was tragically cut short at 38 years old. tonight, an investigation into his mysterious plane crash. what really happened to jfk jr.? man: the u. s. coast guard is conducting a search off of the coast of new york, extending now up to martha's vineyard for a private aircraft that, apparently, has now gone overdue. the coast guard is saying to cnn that onboard that plane was believed to be john f. kennedy jr. cuomo: the situation at the beginning was as devastating as it was simple. what we knew was the plane was gone. they cououldn't find it. it wasn't on radar anymore. the information that we had gotten was that john f. kennedy jr.. his wiwife, and her sister were on a flight from caldwell, new jersey, stopping at martha's vinineyar, then eventntually going to c cape cod. we really didn't have a good sense of what had happened or where they were. amanpourur: i remember when the news first trickled in about john's first disappearance. the internrnational dedesk, as a a courtesy,y, i think,, bebecause theyey knew we were frfriends, calalled m, and theyey said, "have you seen the news?" and, "we just want to keep you abreast of what little we know." bailey: there was a missing-airplane alert, and then in my mind it clicked, "that's jfk jr.'s piper saratoga." i went out to the living room of my friend patricia's house, anand she saidid "john kenenneds plane is missing," and i said, "what does that mean?" and she said, "they don't know." and we a all sort ofof had theos like maybe they ran out of gas and landed on an island somewhere. amananpour: maybe he'd got los. maybe he'd stopped somewhere with his wife and sister-in-law. maybe he was going to come back. berman: rosemarie, john's assistant, i think she said to me something like, "you know what, i bet you the weather was bad, and ththey landed,d, and theyey're at, likeke, at a a holiday i inn somewheh, anand he's goioing to be s o embabarrassed whwhen he wakeke, anand he sees,s, you know,, what's's going on n in the new" i just kept thinking he's going to kill me if this s gets out b because i w hehe's going t to be fine,, and they'r're going toto kill . they'r're going toto be like, "how did you let this get so out of control?" we can confirm that the faa cleared the airplane for takeoff, and the airplane did take off at 8:38 p.m. on friday, july 16th. that plane left our airspace without any problem. what happened after that remains a mystery. the flying community here at this airport hope for the best but fear the worst. did the plane go down in water? were they going toto find the wreckakage? had theyey done a crcrash-land? had d they crashsh-landed into thehe sea, and ththey'd swum m off into - thesese were allll the sortrts of queststions. man: a search i is activelyly undery off ththe coast ofof long isld extending all the way up to martha's vineyard. that saturday was the third anniversary of the twa 800 accident. i had planned to go up to long island. i wawas told thehe coast guauad initiated d a search a and res. we were woken up this morning to a call that a plane had been overdue, apparently jfk jr.'s airplane. hall: we hoped that their job would be successful in terms of rescue so that we would not have to do our job, which would be, obviously, a full investigation. woman: waiting and watching, frank. there's not a lot of news coming out of the family compound. we were the first people on the air with this mystery of, wherere is john n jr.? cuomo:o: there e are just c cameras trad onon the waterer off the v vin. ththere's shotots of the s sh, trying to o get informrmatio. in terms of a news story in my life, it r rarely got t bigger than whatat was startrting to unfn. it w was extraorordinary becee ofof the naturure of the s st, ththe person i involved, and e history of the kennedy family. cuomo: there was only one john kennedy jr. he meant something. he represented something. so the idedea of losining him was so wrorong onon so many d different l les for generarations of a america. [ projector whirring ] lonnstrom: yeah, he was born november 25, 1960. his father had just been elected presidenent of the u united statates a few w weeks befofore that. wewell, now mymy wife and d i pe for a nenew administstration and for a new baby. thank you. tuchman: john f. . kennedy, w when he s presidenent of the u united sta, had thisis amazinglyly beautitiful familyly, whether r you liked d him popolitically y or not. what's y your earliest memory? we had a dog who was named pushinka. we trained it to slide down this slide that we had in the back of the white house. but probably memories of your father are not great? they're great, but they're not plentiful. cuomo: from a young age, john was fascinated with aviation. you could see it in so many of the photos and films that had been taken. right away, there are photographs of young jfk jr. in air force one, holding g airplanes,s, on thehe presidentnt's helicopr inin the pilotot seat. jfk jr. . obviouslyy loved aiairplanes, loved playaying with a airplan, loved d being in a airplanes. lonnstrom: there's a picture of him being held back by his mother because he wanted to run because his fathther was gogonna take o off withoutu, and he thought that was awful. pierre salinger, the presidential press secretary, told me of the f famous imagas of j john runnining to g greet his f father. he would r run right p past hihis father t to that helelic, bebecause thatat's what he really y wanted was a a ride on t that choppeper. one coululd look at t it as a a foreshadodowing but an i inevitabilility, real. he h had to get t up into ththe, and hehe knew thisis beforere he could d even spea. [ camerara shutter c clicks ] thomas: there's nothing remarkable about a photograph of a little kid holding an airplane, but, of course, in retrospect, given how he died, there isis a kind ofof sadnes to thosese photograpaphs. i wouldn't say they're so much ominous as kind of they make you shake your head knowing where fate would take that little boy. andersen: jackie wanted them to have a normal life, as normal as humanly possible. of course, all of that ended on november 22, 1963, withth the assasassination of the p president.. ♪ thomas: when president kennedy was killed in 1963, the country, the world was riveted by the funeral, and the imagage of young john f. kekennedy jr.. salutingng his fatheher's cofn is the i image that t stuck for. that famous picture ththat you must've seen 7 zillion times, the little boy, do you remember that? i think that what happens is that you see an image so many times that you begin to believe, remember the image, but i'm not sure i really do. cuomo: i remember the image well because it became a metaphor, and from that point in his life, jojohn became e more than n a, momore than a a man. he became a moment. he became a message. he became a promise of potential. at this hour, here is what we know. there was no distress call, and there was no evidence that thehere had beeeen any sosort of planane crash. tuchchman: pepeople were stunned because everyone felt like they grew up with john f. kennedy jr. c'mon, we're right there. c'mon baby. it's the only we need. go, go, go, go! ah! touchdown baby! -touchdown! are your neighbors watching the same game? yeah, my 5g home internet delays the game a bit. but you get used to it. try these. they're noise cancelling earmuffs. i stole them from an airport. it's always something with you, man. great! solid! -greek salad? exactly! don't delay the game with verizon or t-mobile 5g home internet. catch it on the xfinity 10g network. kagan: at this hour, here is what we know. dozens of police officers and investigators have resumed their search on land, air. and water for john f. kennedy jr., his wife and sister-in-law. camerota: it was a mystery. there was no distress call, and there was no evidence that there had beeeen any sosort of planane crash. there wawas no wreckckage. i mean, , he had vananished. andersen: : what hampepered the search tremendously was that john never bothered to file a flight plan. now, you don't have to file a flight plan, but giveven the circrcumstanc, it w would've obobviously been thehe wise thining to d. larrabee: the initial search was over a huge area, and because we didn't have a flight plan, they had to go back and look at all that radar data, and so it took a while to do that. we worked at that point with the faa. they were able to determine the flight path of the airplane and determine that it was likely going to be someplace south of martha's vineyard, and we began to sort of focus, narrow down, if you will, the search area. i was just sitting by a television. i mean, as i said, every day, you know, i was,s, you know,, waiting,g, hopingng for the b best. tuchman: people were stunned, because everyone felt like they grew up with john f. kennedy jr. andersen: after the assassination, jackie was devastated, and she decided in 1964 that she h had to moveve back to new yorork city, wherere she basisically grewe. [ camera shutter clicks ] thomas: there's no way that john f. kennedy jr. could have a normal childhood, but his mother tried. my thanks to all of you, and now it's onto chicago, and let's win there. thomas: when bobby kennedy was assassinated in 1968, she said, "if they're killing kennedys, my children are the obvious target." andersen: she married the notorious shipping magnate, aristotle onassis, and instantly the world turned on jackie. they didn't think this was a fitting replacement for the martyred president, but she didn't care, because shshe said, "l"look, he's's got a 75-5-man securirite that can protect my children." [ camera shutter clicks ] thomas: she wanted to make them safe, and aristotle onassis had an island in greece that w was like a a fortress. it w was a safe e place. tuchman: people felt like john f. kennedy jr. was their little boy, and they watched him become a successful and nice young man. [ camera shuhutter clickcking] andersen: when it came time to choose a college, of course, the obvious assumption was that john would d be going t to harvard e ththe rest of f the kennededy, bubut john wasas smart enonoh to k know that the pressure would be unbearable for him, so he decided instead to go to brown univeversity. it's funny, you know, that he actually took a class at brown on his father's administration and got a "b"-plus. [ chchuckles ] amamanpour: i met john first at university. he was at brown university. i was at the universitity of rhohode island.d. we were e in rhode i island, and d we knew eaeach other through h mutual fririends anand struck u up a rereally good d friendship, and d i spent twtwo of my yeys atat universitity shararing a housuse with him. you knowow, he was a an incredi, chcharismatic guy. he was obviously the hot guy, the leader on campus. everybody wanted a bit of him. probably to this day probably nobody really believes ththat john kekennedy clcleaned his s own toilete. he did. i'm herere to tell y you, all ththe toilets s in the hou, whwhen it was s his turn.. the 40th national convention of the democratic party of the united states will come to order. 1988 was the perceived coming-out moment in pololitics for john kennedy jr. he appppears at ththe democrac national convention in atlanta to introduduce his uncncle ted. johnhn fitzgeralald kennedy j. andersen: somebody said that, you know, the air pressure in the entire convention hall, you know,went down dramatically just from the intake of gasps when he took the podium because here was this incredibly good-looking guy that we hadn't seen that much of while he was at brown and speaeaking, realally, for e firsrst time in n his adult vo. thank you very much. tuchman: i distinctly remember saying, "i'm looking forward to seeing michael dukakis, but i'm more looking forward to s seeing john f. kennededy . mamake his spepeech. over a quauarter centutury ag, my father stood before you to accept the nomination for the presidency of the united states. it made people wonder if this was going to be the first of many speeches that would propel him one day to alslso running g for the president t of the uninited sta. so manany of you c came into public s service bececause of . in a very real sense, because of you, he is with us still. and from that point on john the man was a superstar. cuomo: sexiest man, most beautiful man, most desired man, and that's just what i thought of him. jfk jr. was photographed all the time coming in n and out ofof bars with beaututiful womenen. whenen you thinknk of all ththes that he e went out with, it's kind of remarkable there aren't more memoirs of "mymy night witith john," but therere weren't,t, anand i think k that's becece hehe treated women w well. anandersen: hehe was datining e like madonna. he also dated sarah jessica parker. his real relationship, the important relationship began n in 1988 with dararyl hannah.h. it was the longest-lasting of his life. it lasted six years on a and of. woman: john kennedy jr. had arrived with his girlfriend, actress daryl hannah. the couple, apparently shaken by the onslaught, ran into the church. in 1989, he graduates from law school. pass the bar. [ laughter ] he finally had to take the bar exam, and he flunked it once and then twice. "the hunk flunks." these were the headlines. he was mortified. no, it's's absolutelely true. yeah, i i didn't pasass the b. i'm obviously very disappointed but... cuomo: that wound up being one of the biggest albatrosses around his neck. because john was dumb? no. john hadad a learnining disabil. john wouould have bebeen allod to havave the quesestions read to hihim, asas many do,, and he w wouldn't dodo that becaususe he thougught people would d think he w was cheati. [ applauause ] slow news day, i guess, huh? and when he finally, you know, squeaked by the third time, you know, he didn't bragag about t it then eieither. he was excxcellent at handlining the presess withth this kindnd of easasy charm. so is itit true ththat you pasassed the? apparently it's true. i got the official word not long ago, so it's true. how do you feel about it? i'm very pleased. woman: i'm sorry. rob, where are you? [ chuckles ] you know, it tastes pretty sweet at the moment. cuomo: the biggest celebrity today would get crushed like a bug under the amount of pressure that that man dealt with every day, and you'd never know it by looking at him. john was in the tabloids a lot. he knew to expect that. he was a k kennedy. but thenen john met t caroly. john didn't tell his family until like six months later. terenzio: i thinink carolyn n felt that once i it was out, she said, "it wasn't my treasure anymore. it wasn't mine anymore." man: we are closely following the search-and-rescue efforts underway to locate john f. kennedy jr., whose plane has gone missing. john f. kennedy, of course, not alone on that airplane. his wife, carolyn bessette-kennedy, was with him, as well. she, a doctor's daughter, having been raised in greenwich, connecticut. she was voted the ultimate beautiful person by her classmates. andersen: the fall of 1993, john walked into the calvin klein store in new york looking for a suit and met a young personal buyer there named carolyn bessette, this g gorgeous blblonde wiwith pale-blblue eyes, and, you know, he ended up buying three suits and a bunch of shirts and ties and getting her phone number in the process. soon she was a big part of his life. when i met carolyn, she was the head of pr at calvin klein. shshe was very fashionable, very effortlessly chic, clever, charming, funny, intelligent woman. cuomo: what made her special was her spirit. she did not need to be john kennedy's girlfriend, and he was acutely aware of that, and that made him want her even more. radziwill: she always thought that the relationships that you waited patiently for were the only ones worth having. terenzio: if she was your friend, she was your best friend, and she didn't come across that way, unfortunately, but, boy, did people miss out who didn't get to know her. [ camera s shutter clilicks ] berman: yeah, i think the public perception of carolyn was the opposite of what she was. you know, she didn't agree to do any intervieiews, so no one heard her voice, so you wououldn't know -- you u didn't reaeally get a sense e of who shehe was except foror what s she looked d like. andersrsen: we sawaw pictures of carolyn, you know, frowning or running away from cameras. i don't think most people understood the pressures that were on her. it was quite powerful to see them together. their chemistry was really palpable. cuomo: they were both very passionate people. that means you're going to have conflict. yoyou're goingng to be upsp. you'u're going t to have dowo. andersen: there was the famous squabble in the park in which they are shouting at each other and fighting over the dog, and it's really quite heated. terenzio: it was ridiculous. it was over and done with in, you know, an hour, and d they were e fine, bubut it was a all caught t on . bradley: we all felt bad for them because who hasn't had a blow-out fight with a partner? but you don't have it and have the whole world know about it. radziwill: she called me one day and she said, "you have to come down right away." she told me that they had gotten engaged. she told me then not to tell anyone because they just wanted it to be quiet for a while, and i don't think john -- jojohn didn't t tell his f fay until likeke six monthths lat. [ camera shutter clicks ] terenzio: i think carolyn felt that once it was out, it wasn't, you know, like she said, "it t wasn't my y treasure a an. it wasn't t mine anymomore." radziwiwill: they got married in september of 1996. we arrived on cumberland island, and there was not a single reporter, photographer, and not a single soul knew except foror the 40 ofof us whwho were invnvited. it was quite spectacular. terenzio: we all thought that once john was married, the paparazzi situation would subside. it was t the complete opposite. one e of the mosost eligible bachelelors in thehe u.s. is eligible no more. terenzio: people were a little pissed off that he got married. he was supposed to be the sexiest man alive and the most eligible bachelor for the rest of his life. it's a sad day if it's true for all the women out there. it's going to end. they'll get divorced. i wonder, who proposed? she was vilified for taking away the prince of camelot. andersen: john felt he had to actually hold kind of an impromptu press conference on the steps of his condominium in soho and, with her at his side, explain to the press this was all new to her, that he knew how to handle it because he had grown up with it, but this was something the press had to take into account and that they really had to back off and give her time to kind of adjust to o this new l life asas mrs. johnhn f. kennededy. of course, they didn't. as a matter of fact, it only got worse. cuomo: in 1999, john was facing some tough challenges. bradley: political consultants, mone