The recent comic has me 99% convinced that Reaper joined Talon in order to take them down from the inside.
The amount of anger Gabriel has toward Talon, his willingness and conviction to do whatever it takes to see them pay for daring to hurt his organization, the Reaper foreshadowing on the last panel while he says ‘I don’t play by those rules either’.
Not to mention the symbolism of Reaper dressing as the Red death in a previous comic. His reluctance to kill Jack and Ana when he’s had the chance.
His lines about getting vengeance (and who’s hurt him and the people he cares about more than Talon has).