It's canon status is: canon.
Wandering the streets of New York on his day off Drake stumbles upon a small library, with free wifi and a coffee stand, where he soon finds himself in the company of Lauren Frost though he doesn't know that until a bit later.
After a brief conversation Drake agrees to go to Equestria, though at the time he didn't truly believe she could send him there, and is then whisked away to the land of ponies. Waking up moments later he finds himself in Equestria, much to his joy and fear, and discovers that he is in the barracks of Canterlot Castle. Not wanting to be thrown in jail for breaking and entering he begins to leave only to discover that he has taken on the form of a Draconequus. Before his sudden transformation could register Philomena, Celestia's pet Phoenix, comes in and alerts the guards to his presence by smashing a vase.
The guards mistaking him for Discord alert the inhabitants that he has escaped and begins chasing after Drake. Drake, at the time, with no means of defending or negotiating with the guards decides to flee beginning an epic escape of random/silly events. Starting to scratch the surface of Chaos magic he is about to get away only to run into Luna who captures him and begins to question is very presence since Discord was still encased in stone. Thinking about the odd events that played before Drake tries to actively use it to his advantage, in hopes of escaping, though fails as Luna sends him face first into the side of the castle. A few moments later Drake finds himself within his own mind where he meets his other half Derange and his game master Lauren Frost. They spend a few minutes talking about what is going on and why Drake was brought to Equestria to begin with. Drake agreeing to do Lauren's bidding and restoring the scale of order and chaos soon finds himself being challenge for control by Derange. After the battle of spamming Drake finds himself victorious and awakens in the last place he wanted to be...in jail.
After a few moments of waiting in his cell block he is surprised to see a disheveled Celestia followed by Luna who ask if he is Celestia's son Disarray. Answering her truly she is sadden by the news, but quickly recovers as they discuss who, what and why he is here. Releasing him from his bindings they offer Drake a room for him to call his own and with nothing better to do both him and Luna go to get some breakfast though had to leave for a moment to finish some filing some paperwork. After some more shenanigans, involving a trollish hell spider, he returns to his room and begins thinking about who he could travel with in helping fix the scale only to be interrupted by an invitation from the Princesses wanting to discuss more in depth about his objective. Explaining the reasons and why they need him the Princesses reluctantly agree, but add a condition stating that someone they chose would accompany him. Agreeing to the conditions Drake returns to his room, after trying to get some information on the other pieces with little results, and hours later summon Derpy and Minuette to his room, but before he could fully explain who and why he brought them here is interrupted by Silver (aka there babysitter/chaperone). Finally explaining and persuading them to come with him they meet up later at the front of Canterlot Castle and head off towards the train station heading towards the 'source' or the beginning of the Chess Game.
A week pass as they arrive at Wethoof and separate for the day: Drake and Silver going to inspect the heart of the chaotic energy while Derange, Minutte, Derpy and Dinky relaxed in the village. Drake and Silver arrive at their destination as explore the surrounding area find some noting noteworthy. Going into a state of unconsciousness Drake finds himself in a void of images of the other chess pieces and their accomplishments so far only to run into an unimaginable creature causing him to be forced out of the visions, but to forget about the creature altogether. Regrouping back into town and resting for the night they soon head out towards the Volcanic Waste while on the way spreading order and chaos around.
A few days into traversing the waste Derpy spots some activity, curious as to what is going on Drake and the group make their way over towards it and find themselves face to face with a group of slavers.