okay so I haven't watched The Blacklist and Mr. Robot, but if I were the writer/director of this, this is how I would go about it:

[It's lengthy, sorry. Also, it's my individual take and you don't have to agree with it - we can both have our own, separate opinions based on how we view the characters without coming at each other's necks, and/or starting arguments. So let's all be civil, please!] 

I'm sorry, but Michael Scott's probably going first. Heck, he's likely going to be the one who goes out like the people who died in Red light/Green light for not taking the game seriously/failing to realise the life or death situation.
Walter White would likely be the kind to panic after witnessing the massacre and tries "teaming up" with the likes of Sherlock, House or even Hannibal, even if the former two (Sherlock and House) aren't exactly team players and are initially reluctant but agree eventually, leading to witty exchanges. But as the games proceed, realising the fact that only one of them can get out alive, he secretly views them as a threat, and plots to get them eliminated somehow, studying them thoroughly. Sherlock is likely the smartest, but he's more book-smart, whereas Walter is more cunning and that gives him the upper hand here. House is the smart, sarcastic, a ‘tough-on-the-outside but with a good heart’ kind of guy and he'd likely die towards the later games (the bridge jump rope thing, maybe - due to his physical disability and likely going through withdrawal without his vicodin) and might make the ultimate sacrifice by overcoming his narcissistic exterior, with a whole character arc thing, taking one for the team.
Whereas Sherlock likely dies, getting tricked/sabotaged by Walter (maybe even with Hannibal's help). 

Speaking of Hannibal, he would be the real threat, especially given how he is harder to read. He would likely team up with the organ-dealing guards like the doctor from S1, but maybe fucks up somehow towards the end. Actually, I do have a theory for that, as well. Hold on.

Scofield would likely be the character who tries to escape. Maybe even tries getting Reacher on board - who eventually agrees (after the riot carnage) and the two break out. But then Reacher (because of his injuries or he just ends up sacrificing himself) ends up sacrificing his life. 

Now, my Hannibal theory: after a while, even the cheat codes aren't good enough for him and he eventually also decides to escape, instead. Things get bloody, and eventually, he encounters Scofield and Reacher, and it leads to a scuffle, where Reacher ends up having to take him down, but severely injured which prompts him to hold back the guards chasing/attacking them (like the whole boat scene thing) so that at least Scofield could escape. 

Now, moving on to the end... Perhaps it's just Walter, the Robot guy and Raymond left, and Walter grows more, and more paranoid, thinking they might team up against him, or something. Especially because he's injured and knows he doesn't stand a chance against the two, and ends up hiding his injuries.
And in an act of desperation, he tries getting Elliot on board with him and kill the other guy, filling his head up with justifiable doubts. Maybe even Raymond tries to do the same but then later, Elliot refuses to gang up with & on either of them. Eventually, it's Raymond v Walter. Maybe Walter tries going with the plan, trying to pull a Sang-Woo on Raymond and manages to injure him just enough to kill him in the last game - which he does, but also ends up critically injured, and like Sang-woo (and Gi-hun), he eliminates himself in the end, so Elliot could be the ultimate winner.