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This is funny because I have the poor mans version of each. A standard 1861 and now the Tudor GMT lol.
So If I had to choose to upgrade one of them???......
I hate to say it but probably the Rolex - if this was like, my only watch to wear every day.
But hypothetically, if I were to still keep the Tudor, I would upgrade the Speedy.
I need some more context to make a real decision here hah.
Both are the current models.
Assuming you mean "an opportunity to purchase at MSRP," and given the number of absolutely bonkers people on earth right now who will pay 2X or 3X MSRP for an OK steel sports watch because it's a flex piece... I'd take the Rolex and shortly thereafter somebody's money.
Edit: If you mean supply is no longer an issue and the market is not still insane, the 321.