Who do you think is the "riskiest" champion to rework, in the sense that it needs a rework but the playerbase is so much attracted to the live representation that might not like many changes? I think it is Kayle: her E is nice early-mid game but then becomes a dumb E spam but people like her ranged

Enrico Boccardi
I think Fiora recently was an example of a risky rework. Gameplay-wise I think she really needed the work and I think the end result was really solid (despite her being OP on post-hotfix release) but the difficulty comes more in communicating the priority rather than the result. While the work was nowhere near in scope to similar appearing larger-scale reworks, I think it's a tough sell to many players why the team prioritized her over a number of other champions.
I feel the riskiness of reworks are less about players being attached to the current version and more about does this champion make sense to rework before some of the longstanding ones that also need help (Poppy, Yorick etc).
As for Kayle specifically using this mindset she doesn't really tip my radar as being risky. While not visually offensive, her visuals are really out of date by today's standards. Creatively I think she needs a small hook other than "Angel?" and gameplay-wise she's okay but certainly not as cool as she could be.

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