This is mainly meant as an explanation for why I think the footage of Masky in Extraction was recorded at some point prior to January 2011.

April 2010

Masky's leg is broken shortly after 21st April 2010 (Entry #35). We don't see him immediately after this but I think it's safe to assume that he wasn't doing much walking right afterwards.

July 2010

The next time we see him is "Approximately three months after [Jay found Alex]" - which means it's three months after April - in Entry #45. In this one Hoody lures Alex all the way from his house into Rosswood Park so Masky can attack him there (which is actually so sweet of him <3). The video is very blurry but it seems like he has some serious trouble putting weight on the leg, which makes sense:


However, he does tackle Alex to the ground right before this so I would say his leg is healed to the point where he can do short sprints, but not walk for long periods of time.

October / November 2010

Next comes Entry #50 and #52. It's unclear when exactly Jay and Alex's trip into Rosswood from Entry #38 and #50 takes place but it can't be too long before #52 and that takes place on the day before #27 so 22nd November 2010. In Entry #50, Masky is hanging out in Rosswood Park (as he does) and starts running when Jay spots him, leading him to the tunnel. The video is too shaky to see how he's moving but what's notable is that once they reach the tunnel he actually manages to *outrun* Jay.

So six to seven months after the Leg Break he can already walk and run pretty well again.

January 2011

On the fated night of Entry #33 and #76 - the 12th of January 2011 - nine months after the Leg Break - Masky famously does the following things:
  - walk all the way from Rosswood Park to the hotel
  - carry a grown woman down two flights of stairs and into Rosswood Park
  - walk all the way back to the hotel AGAIN
  - chase Jay out of his hotel room
  - walk back into Rosswood Park. again.

And he is still limping here:

Slightly. But given that he does *gestures upwards* all of that, it can't be a huge inconvenience anymore at this point. Also since Hoody went through the trouble of bringing Alex to him in Entry #45 when he REALLY couldn't walk, I don't think he would have let him walk around this much if he hadn't been able to handle it.

September and November 2011

On 27th September 2011, Extraction was uploaded. This one famously features a shot of Masky walking towards the camera:


The Leg Break happened ~17 months (one year and five months) ago and as described above, his leg had already healed to the point were he could run and walk around months before this (in January - eight months prior). Here he seems to be walking with more difficulty.

Only two months later - in November - Jay spots Tim in Rosswood Town:


He isn't limping at all anymore. If the footage from Extraction had been from September (or around that time) there is no way that his leg would have healed this well in that short amount of time.

Le Epic Conclusion

So in conclusion I'd say the footage is definitely older than September 2011 and more likely from between July and November 2010.

List of events that happened on the dates shown in enttry #37 (and which fit the death/disaster theme):

1900-06-03 - 8:23 PM

- Adventurer Mary Kingsley, who had written two bestsellers about the various peoples of West Africa, died of typhoid fever at the age of 37 in South Africa. (link)
- An outbreak of the bubonic plague in Sydney Australia leaves two dead. (from the wiki page, credited to "CrimsonGhost713")
- A cholera outbreak in India kills five thousand in less than four days, the dead lie unburied in the streets for days. (from the wiki page, credited to "CrimsonGhost713")

1999-07-10 - 6:03 AM

- Train Kills Pedestrian At Crossing; Witnesses Tell Police She Knelt and Waited (link)
- Andy Wallis goes overboard on a cruise ship, Walter R. Evans dies. (link)
- Cultists kill 5 students at Obafemi Awolowo University in Nigeria. (link)

1891-08-30 - 1:00 PM

- A child goes missing at a Wichita train station (link)
- Glenni William Scofield, Republican member of the U.S. House of Representatives, dies. (from the wiki page)

1988-05-17 - 9:00 AM

- Joseph Lee Saldana died of a single gunshot wound to the head minutes after the accident occurred at his father's apartment (from the wiki page)
- [OOG]: Troy's IRL birthday apparently

1991-09-04 - 10:48 AM

- Worries about Africanized killer bees/hornets and how many children they'd killed in Mexico/if they would move to America (link)
- Charlie Barnet dies of pneumonia at 77, Dottie West dies at 58 in a car, Margaret Ramsay dies (cause Unknown), Thomas Tryon dies at 65. (from the wiki page)

1992-01-01 - 12:00 AM

- An eighteen year old Canadian girl goes missing while in Halifax, Nova Scotia looking for work. She was later discovered to have been killed in a homicide. (from the wiki page)

1996-02-29 - 4:44 AM

- In Lumberton, North Carolina, Daniel Green is convicted of the murder of James Jordan, the father of basketball star Michael Jordan.
- A Boeing 737 flying for Faucett Airlines in route from Lima to Rodriguez Ballon airport crashes into a mountain near Arequipa; all 123 people on board are killed.
- At least 81 people drown when a boat capsizes 120 kilometres east of Kampala, Uganda. (link for all 3)
- Dennis Yau, a 5-year-old boy, was killed when a television set fell off a stand onto his head (from the wiki page, credited to "DJJK")

1999-12-31 - 11:58 PM

- Five hijackers, who had been holding 155 hostages on an Indian Airlines plane, leave the plane with two Islamic clerics that they had demanded be freed. (link)
- The Y2K panic (link)

1981-03-03 - 9:42 AM

- Mehmet Ali Ağca given the instruction to kill Pope John Paul II. (from the wiki page)

1993-11-12 - 12:34 AM

- H.R. Haldeman dies after refusing medication due to Christian beliefs. (link)

1944-06-06 - 9:99 AM

- WWII – Battle of Normandy: Operation Overlord, commonly known as D-Day, commences with the landing of 155,000 Allied troops on the beaches of Normandy in France. (link)

1991-04-04 - 6:03 PM

- Senator John Heinz of Pennsylvania and six others are killed when a helicopter collides with their plane (link)

The most common interpretation of the sequence of events shown in Entries #58, #60, #61 and the TTA videos Reference and observation is that Hoody somehow got wind of some kind of lie that Masky or Tim (depending on who you ask) told him and then gave the medical records to Jay to prove that somehow. And by "most common interpretation" I mean that in my 10+ years of being in this fandom I've never seen anyone even so much as question this. I don't consider myself very good at media analysis so I always assumed this was either a plot hole or that I was just missing something because this never made sense to me.

And then a few months ago I finally sat down and watched the Creators' Commentary for all three seasons of MH and when I got to the one for Entry #60 (the part where Jay finds the "He is a Liar - Follow Me" message) I almost fell out of my chair because Troy just casually confirms that I was right all along:





The medical records were not (originally) meant for Jay and they also weren't meant to reveal some dark secret Tim had been hiding. That way this whole situation actually makes sense, because Tim barely knows Jay at this point so him not telling him about his personal medical history isn't "lying" it's just. normal behaviour. Jay on the other hand is lying to Tim about wanting to finish Alex's movie. That's what the "He is a Liar" line is about. What Hoody wants to achieve at this point is for the two of them to work together so if he was warning Jay about Tim for whatever reason he would be shooting himself in the foot. He's trying to make Tim see that more is going on and that it's something related to his past. Basically if Tim and Jay had found the medical records together (and if they had read the message first) Jay would have been forced to tell Tim the truth right then and there.

So in this original plan Hoody was trying to orchestrate a situation where Tim would learn the truth in a way that probably would have freaked him out but would otherwise not have caused him any lasting harm. This was Hoody trying to be NICE. "But why would Hoody be nice when only 3.5 entries and 2 totheark videos later he's stealing Tim's pills to trigger a seizure?" you ask. And that's exactly the right question because this is where things get interesting:

Interesting and also awsome because I think this was one of the coolest ways in which the multiple media formats MH uses (TWO youtube channels and the twitter account) have been combined.

After Tim finds out about what Jay has been doing on his own (Entry #59) the only way to get the two of them together is by forcing them to be in the same space. That's why he tells Jay to get the medical records in "Reference". The full message in that video is "Truth with light - His lies in the dark". It's tempting to interpret the word "lies" as a plural noun and that of course seems to support the idea of Hoody accusing Tim of lying. But when it's read as a verb, it simply connects the phrase to the one that precedes it and the message becomes "Truth with light - His [truth] lies in the dark". Because the medical records (the catalyst for Tim learning the truth) are still in the (dark) tunnel.

In Hoody's original plan the medical records were simply meant to be a conversation starter. Now their purpose has shifted and they're actually meant to give some information to Jay - where Masky will go when he fronts. But because of the way this whole thing was presented this is difficult to understand for the audience. Like I actually think this is the only genuine mistake in the entire series and I wish they had spotted this while editing or reviewing or whataver but. Alas.

Anyways the next relevant thing that happens is Hoody hijacking the Twitter account from 30th July to 8th August 2012. During this time he posts multiple tweets referencing storms as well as a screenshot and the link to the video "observation". On the surface, that might seem like typical Hoody behaviour since rain and water are common motifs in totheark videos and hacking accounts is also a thing he does but this time there's actually more to it than that.

Posting links to totheark videos on Twitter is normally a thing Jay does but it often takes him a few days to do so (e.g. he linked "Sidetone" four days after it was posted, "Reminder" three days) and sometimes he even forgets completely (e.g. "Messages", "Classified"). This is the only time a totheark video has been linked on Twitter by anyone other than Jay and the link was posted only a few hours after the video was uploaded AND it was preceded by a screenshot from the video as well. In other words Hoody wanted to make really really absolutely 100% sure Jay would see this one. Which is interesting because the video itself is so unremarkable. It doesn't contain any messages, the description is in cleartext and even the visuals themselves are just Tim in his house with the Masky mask briefly appearing over his face. But let's move on for now.

Next come the storm-themed tweets. The video Hoody posts of himself breaking into Tim's house opens with a shot of a storm and Jay points out in Entry #61 that "There was a storm earlier" which suggests that "[the] video was shot just a short while ago". So we can assume that the tweets were referencing that particular storm which most likely would have been on the weather forecast for days before all of this happened. In other words, they were a time indicator.

So what do we get when we put all of this together? I'll tell you: The Twitter hijack + "observation" were Hoody announcing what he was going to do to Tim several days in advance. Why would he do this? So that Jay would be prepared to act when he actually did the thing. He even states in "entry"/Entry #61 that "This is [Jay's] only chance". Because he doesn't actually want to hurt Tim but after his much nicer plan in Entry #58 didn't work out this was the only alternative he saw. And this is Jay's only chance because he knows (academically and/or from second hand experience since he knows both Tim and Masky personally) that triggering a seizure and forcing Masky to front is a terrible thing to do and he's not going to do that to them a second time. That's why he tried to make extra sure that everything would work out this time by preparing Jay: "Reference" telling him to get the medical records so he'll know where to find Masky, "observation" telling him what he's about to do and the storm-themed tweets telling him when he'll do it.

And that's it. No malice towards Tim involved. On the contrary, Hoody was actually so nice to him because he likes him. "But then why did he and Masky 'split up'?" you ask. Because Masky just stopped fronting after Entry #32/33/76. That's literally what we see happen on screen and it's supported by pretty much everything Tim says in Entry #59. Occam's Razor is satisfied and so am I.