PC: Tudor penal colonies in New Word

Just as it says on the tin. I've heard varying statistics on how many people were executed on the orders of King Henry VIII, the highest being nearly 72,000, and I've been wondering: what would it take for Henry VIII to decide to exile those people to the New Word instead? Would it work? Might Henry VIII decide to commute the sentences of lesser criminals if they agree to go to the New Word?
 
Well, for starters Henry would have to comission a new world colony, and this would take funds away from his ultimate goal of mimicing Henry V and reclaiming the throne of France.

This might rely on Henry VII funding Columbus to get things off the bat.
 
Cost is one factor as in the fact that most of the people Henry VIII killed were people he wanted dead (i.e. rebels/anyone saying no to him) not just a long way away.
 
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