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 ago). 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)