His odds were very good - better than 50-50 for a straight 6, and outright failure had less than a 7% chance. Success+complication could have moved him to a more dangerous position, but given that he could resist most likely immediate harm (what would have been a success to keep the server quiet, but a complication that doesn't obliterate that success?), he likely would have been able to weasel out of the situation if he'd needed to.
But the truth is, that isn't really my point. My point is, roleplaying -- and especially roleplaying with strong narrative, like Blades in the Dark -- is always telling a story. And there's a decision, influenced by the system, the GM, the group, of what kind of story to be telling.
The stories being told in this episode weren't stories of risk-taking, even when risks were being taken. The focus, the emphasis, weren't really on "here's the dangers you're facing; here's how awesome you are for overcoming them." The risks were minor speedbumps on the way to getting to the scenes of execution. Playing out the execution -- the detail of the fates Aldo and Carriless had in mind for their victims; their own mindset when performing the kill -- that's where the focus was.
And don't get me wrong -- this isn't a criticism. It's an observation. It's not a criticism because,
(a) I think it's absolutely fine to decide that that's the kind of story you want to tell. It's got drama, it's got character, it's got disturbing darkness, and that makes for good stories (for a certain type of "good").
And because (b) it's not any one player pulling towards this type of story; we've seen plenty of other tones and styles in the series, and these particular scores and opportunities really lent themselves to this particular approach.
For myself, this ties into the one issue I do have with Rollplay Blades so far -- I'm waiting for them to tangle with some more determined opposition. So far, they've pretty much disposed of each enemy that's cropped up; haven't suffered any entanglements that were more than momentary setbacks; and haven't made any enemies inclined to take the initiative (at least as far as we've seen). It's not surprising that play style should drift into "murdering people who can't put up much in the way of a meaningful opposition," because so far a meaningful opposition just hasn't really been established. (I haven't seen Episode 10 yet, but it sounds like that's very likely to change -- with the fallout from Grace's death, plus taking on Skurlock and Sitara, who I expect will be capable as hell.)
I think it's fascinating how different crew types and play styles affect the game -- a crew of Shadows, for example, doesn't have nearly the same opportunity or ability that Assassins do to get rid of enemies. Shadows, as thieves and spies, are also forced much more into their enemies' strongholds -- vs. assassins, who, at least for incautious targets, have the option of drawing their foes out where they're unguarded (think of all the times victims didn't get the benefit of their Tier, because the crew cut them off from it. Or of how the toughest score was where they had to beard their target in his stronghold) . It makes for a very different game. Of course, as the crew progresses, makes enemies, rises in Tier, gains more assets they need to protect, that's likely to change as well