Between these, the Speedmaster Professional would get my vote. It is known for its rock solid movement, where the Monaco leaves something to be desired in that category. The obvious Rolex to include here is the Submariner. However, I think the Explorer, Datejust, and GMT all would be equally meritorious.
What the heck is the 10-0 countdown on the yachtmaster dial/bezel used for?
Also, of those 3 the only one I'd consider is the Speedy. The Monaco would be a distant second, and the yachtmaster is not one I'd wear unless my wife gave it to me as a surprise and told me it was her favorite watch ever and I had to wear it to prove my undying love for her. And even then I wouldn't wear it out in public.
Rolex has many iconic watches, such as the Submariner, Explorer I/II, and GMT, but I suspect the flagship is their SkyDweller (previously the President Day-Date).
Flag ship normally means what the brand is most known for and sells the most of, is it not? I know Sierra Nevada Pale Ale is their "flag ship" though certainly not their best or more impressive beer. Other than teh Omega I'd be flabbergasted to see either of those other two meet either criteria.
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