I'm always taken by the story of Flora MacDonald who aided Bonnie Prince Charlie escape on the famous Skye Boat after the Battle of Culloden in 1746. While Charles Edward Stuart (disguised as a maid) made it back to France, Flora herself did a stint in the Tower of London for her pains.
30 years later, however, during the War of American Independence Flora was an ardent loyalist (this time for the Hanoverians) in North Carolina where her husband Allan (also from the Hebrides) was a British army officer. She and Allan returned to Scotland when that cause too was lost.
MacDonald maintained that her giving help to Charles Stuart was motivated by humanitarian concerns rather than ideological ones. That could have been a case of telling the victors what they wanted to hear but either way hers is a remarkable tale of having been loyal to the losing side on both occasions and yet emerging with dignity intact.
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