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User blog comment:Blackout S1E7/Most Experienced Assassin?/@comment-27020644-20151212220817
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Firstly, Haytham Kenway wasn't an Assassin.
Secondly, I think it's hard to decide. As you said some are stronger while some are stealthier.
Another big factor would be their equipment. For example, Altair only had one hidden blade while later Assassins had two. Edward, Connor, and Shay had ships. Ezio had a parachute. Connor, Edward, Shay, Aveline, and Ezio had flintlock pistols while Jacob and Evie had revolvers.
It really depends on what definition you are using for skilled.
The most skilled could be Altair as he didn't rely on much technology for his missions, or it could be Edward who fought on land and sea.
Also, is the most skilled the one that can kill the most or the one that kills the least?