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That is, Henry Frederick, the ill fated son of James I...

The boy seemed to show a lot of promise, although he disagreed with his father on many matters and didn't get along with his younger son. Apperently their were talks regarding the prince marrying Catherine de Medici, a daughter of the Grand Duke Ferdinand who employed Robert Dudley's illegitimate son for some time. The marriage idea ultimately broke down because of the difference in religions, but I see it rather a small hurdle, given James designs later in his reign regarding a match with Spain.

What if the Prince of Wales married Catherine de Medici? In 1612 they are both a little old for the marriage game -- he's 18 and she is 19. Dudley's son was in correspond with the Prince and suggested the marriage in 1611. If Henry is surrounded by fewer radicals (he was a pretty deep Protestant), the marriage has more success. Let's say the Prince agrees but only if he meets the Tuscan Princess, going on a grandtime sometime in 1612 and lasting most of year, causing him to miss catching tuberculous and dying.

In Florence, Henry makes a great impression on the Grand Duke and his court, and although Catherine is unwilling to convert, she is willing to marry the Prince of Wales provided she can practice her faith in private. Henry returns to England esctatic and negations between Tuscany and France go off without a hitch, especially when a generous dowry of £600,000 is offered to pay the debts of James I and alleviate the difficult financial situation James I is facing. The treaty is agreed upon and Catherine arrives in England in the Spring of 1613, accompanied by Robert Dudley, the illegitimate son of the Earl of Leicester, who is possibly restored the Earldom of Leicester as well as that of Warwick? (Leicester seems likely especially if Robert redeems himself, but Warwick and it's castle, which belonged to his uncle Ambrose Dudley seems much less likely).

What happens next? I can see Parliament having some difficulties accepting the marriage, but will ultimately they can't really stop it, as Parliament didn't really interfere in matters concerning the royal family and the succession, at least not until the Act of Succession. They may become intransigent regarding future funding, even more so than OTL, but shouldn't be any huge issues, perhaps some small scale riots in London and other anti-Catholic hysteria, although certainly nothing like it was IOTL 1680s...

The 17th century Jacobean Parliament was starting to be more bold, but they still didn't interfere in matters of the royal family, including their marriages. The dowry will certainly aid James, much as the dowry of Marie de Medicis aided Henry IV with his own, a major plus. The only down side is it will most definitely sour James' relations with Parliament even more, and another hurdle being Henry's rather intense faith: he may find marrying a Catholic hard to stomach. But if he begins smitten, he nay be able to conveniently ignore that fact.
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