Catching a glimpse of a few of Jack's more recent videos - including the "Karen videos" that landed him on the show - he is your typical teenage YouTuber that will do anything to get himself attention. But his pranks and antics are not malicious. They are what they are just pranks.
Of course his mother is concerned about his school-work and academics. She's been featured in many of his videos expressing this very real concern. His father is worried too, but realizes that his is his son's lively-hood. It's the way he makes his money. And finally his older brother, Michael, has been pulled in to some of Jack's pranks - whether it's on his own accord or not remains to truly be known. So the entire family is supportive of Jack's YouTube career.
Now where he has pushed the envelope is with his more recent "Karen videos" which all started with him riding his motorized dirt bike behind with a friend behind an old church that had a hill. The neighbor did not like it and called the police. When Jack and his friend saw a cruiser drive by to patrol the neighbor, they left.
A few days later, Jack and his friends went back to the old church to ride their bikes and that's when all hell broke loose. A woman (Rachel, but nicknamed "Karen" by Jack) came walking across the church lawn to confront Jack. In a harsh tone she said "you can't be here; you're not allowed here this is private property."
Sure it was private property and Jack and his friends should not have been riding their bikes there, but it was not Rachel's job to walk across and confront him. If it was her property, it would be a different story. But she came across the street and verbally accosted him. Jack being only 17 years old did the only thing he knew, he hastily quipped back at her and that's when everything blew up.
Her parental instincts took over and demanded that she speak to his parents. He gave her his address and she showed up at his doorstep. At the moment his father wasn't home, but when Jack called him and said Rachel was at their house he knew he had to come home and speak with her.
Rachel expressed her concerns to his father - some were very real (i.e. not wearing a helmet), but the others appeared to be disguised as a her frustration of his "lack of respect" towards her. If she was able to disassociate and look at the scenario as an outsider, she may come to the realization that the way she approached him from the beginning was not respectful to him (i.e. marching across the front of the church and screaming at him).
She also began to take exception that he was using her as clickbait for his channel. Which, when she came to his house, he had every right to film her. He went the extra distance to blur out her face and have his lawyers oversee each video - which in billable hours, costs a pretty penny. Once his lawyers and manager deemed appropriate, he posted the video. But she kept coming back on two other occasions (confronting both his friend and mother) and harassed him to remove the videos.
Now here's where Jack went wrong. Seeing this was getting good content and his fans wanted to see him continue to push the limits, he drove his dirt bike past Rachel's house, forcing her to come outside and call his father. A few days later, he went further and decided to "ding dong ditch" her, making her come to his house again. These two instances, Jack clearly was in the wrong.
If he did not do these two things, things probably would have blown over. And if Rachel continued to come back to his house and forcing him to take down the videos, she would've been at fault for disturbing him. But Jack's only 17 years old so he wasn't thinking that way. (Not an excuse but a reason.)
On the Dr. Phil show, when they brought Rachel in via phone. She sounded pleasant and nice, but came across as though she was trying to parent Jack herself. Jack issues an apology to Rachel for antagonizing her, but she doesn't accept that apology. She responds that she "doesn't know he knows how to give a genuine" apology.
It's evident he doesn't know how to do that. He's only 17 years old, (again not an excuse), but it's not her job to make him realize that. She can't force him to understand that; he needs to come to that conclusion on his own. When it all boils down it's Rachel, the adult in this circumstance, stooping down to his level and trying to to teach him something when that's not her responsibility. She should've accepted his "apology" however it was worded even if she didn't wholeheartedly agree with it. It would've been water under the bridge and everyone would've moved on.
A good apology, according to the late Carnegie Mellon professor Randy Pausch, has three parts: 1. "I'm sorry;" 2. "It was my fault;" 3. "How do I make it right?" (Most people skip that third part.)
Jack was attempting the third part with his offer to come over and do what whatever she wanted, but she continued to educate him that's not how an apology works. Well, Rachel, that is how an apology works. He was trying to do the third part. He was trying to make it right. Rachel wanted it one specific way, her way, and wouldn't budge from that.
I feel bad for both of them. Neither deserved this, but Jack was being a picked on by someone who should know better and not worry about what her neighbors are doing. Because in the end, he's no different than her and she's no different than him. He earned the money he made. They are both humans.
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