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I'll start by saying I've never held a Duke because I didn't get my OG Xbox until 2004, but it looks awkward and I'm not surprised that Xbox replaced it mid-gen with the OG Xbox S controller. I remember really liking the ergonomics of the OG Xbox S controller, but I haven't held one in over a decade and the black and white buttons are clearly inferior to the left and right bumpers that replaced them on the Xbox 360 controller and have stayed ever since. 360 had pretty good ergonomics but was held back by the exterior battery pack causing finger cramping during longer gaming sessions due to your fingers being smooshed up against it. Xbox One fixed the battery pack issue from the 360 and overall improved the ergonomics, but had issues with stick drift and right and left bumpers that were too hard to push, pretty major issues imo (both fixed on the mid-gen refresh XB1 controller). Lastly we have the Xbox Series controller, which has the best ergonomics of any controller currently in my possession to hold and compare, an improved d-pad, easy to push shoulder buttons, and a share button, easy win for Series imo.

Xbox Series > XB1 refresh > 360 > OG Xbox S > XB1 launch