It's hard to tell, because your tree is marked private and we cannot see it. But my guess is, considering how far back in time James Winslow lived, that you are at the limit of how far autosomal DNA will propagate in Wikitree. Your test will only show up on profiles for people within 8 degrees of separation (your parents are 1 degree from you, grandparents are 2 degrees from you, etc.) Is James then your 6-great-grandfather? Your DNA test would then propagate to him, but no farther. This is reasonable, as it is very, very rare that autosomal DNA can be used carefully to gain a confident confirmation of a 7-great-grandparent.