Officer Dibble
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How you describe it, it all fits in. Especially the fast walking in the heat. JMOIt's highly probable that a guy walking around thar area of Tenerife wearing a genuine Rolex is involved in some capacity with organised crime. The fact that the theft wasn't reported to the Police would support that. The watch could have been legitimately owned by the individual it was stolen from, but generally members of organised crime fraternities don't go to the Police when they've become the victim of a crime. They deal with it internally.
One of the two occupants of the AirBnB (who can't be named here due to forum rules, but has been named in MSM) has a criminal background, and if his Social Media history is anything to go by, is a bit of an arrogant loudmouth who fancies himself as a 'real gangster.
I suspect that the two AirBnB occupants were the ones orchestrating the watch theft. Bear in mind that Jay is only 19, suggestible (JMO but his pre-tenerife history paints him as a follower rather than a leader) and likely starstruck by the criminal backgrounds of these two men. It wouldn't take much to convince him to play a minor role in a watch theft, especially after a few drinks and the promise of a cut of the profits.
Watch gets stolen, and the two men hightail it along with Jay to their AirBnB.
Along the way, buzzing from the heist, Jay sends a Snapchat boasting about how they just robbed some foreign bloke of a £12K Rolex.
Back at the AirBnB, talk of the Rolex continues on Snapchat. Still drunk and buzzing from the theft, Jay mentions that the two men have passed out and that he could literally walk out the door with the Rolex and keep it for himself.
Somebody on his Snapchat thinks that's a great idea and dares him to do it.
Jay pockets the watch, leaves the AirBnB and meets Ofelia who tells him he'll need to wait for the next bus.
That's no good to Jay, who needs to be gone before the two men wake up and notice the Rolex (and Jay) are gone.
Jay figures he needs to get away from the Villa sharpish and decides that if they went looking for him, they'd head south back towards the Beach to his Hotel.
Jay decides heading North is the safest bet until he loses the heat.
Two guys wake up. No Jay. No watch.
They head outside and meet Ofelia who tells them that Jay went north.
They get in the car and head up into the hills to catch him.
Jay is on the phone to Brad, possibly buzzing about the fact that he actually stole the watch, at which point he sees the hire car making its way up the hill. Bollocks. Time to hide.
Tells Brad he needs to go and hangs up before moving off road into the brush.
After a few minutes of moving around staying well away from the road, the adrenaline wears off and he realises he doesn't know where he is.
Starting to panic about the fact that he's lost, dehydrated and being chased by two guys that (to him, at least) resemble Tony Montana and Whitey Bulger, he calls Lucy (who knows the island best) to ask for help.
He tells Lucy about what he's done with the watch. Lucy, who knows these guys as 'associates' immediately panics over what Jay has got himself into and after likely telling him to 'drop a pin before your battery runs out and stay there', gets off the phone and immediately calls the police to report him lost, hoping that they can get to him before Tony Montana and Whitey Bulger can.
The next part is anyone's guess. Tony and Whitey either catch up to Jay, or Jay gets further into the brush and ends up succumbing to shock/dehydration/heat.
After alerting the Police, Lucy gets in contact with Jay's social circle to find out what everyone knows, and advises Jay's mum of the situation - including the watch theft - prompting Jay's mum to assume that the two men have captured her son and pleading for him to be let go.
Lucy gets to the AirBnB. "WHAT HAVE YOU DONE TO JAY?!"
The two guys, suprised that she's appeared there, explain that Jay stole the watch, but swear to her that they were not able to find him.
The Police visit the AirBnB. The watch has not been reported missing, so the Police have no knowledge of any watch theft.
"Yes, Officer. Jay was here last night, but when we woke up in the morning he was gone. We went looking for him, but he was nowhere to be seen".
There's no suggestion of foul play, or of any crime at all having been committed. The men's statements are taken and they're free to leave.
The more I think about this, the more it makes perfect sense. Particularly Jay's decision to go North as opposed to South, and the fact that Ofelia remarked that he was 'walking fast'. Bearing in mind that according to his stepfather, he was not fond of walking at all. This isn't the kind of guy that goes on a hike because it's a nice day out. He had to have a reason for going that direction. I think the reason was losing the two men.