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If Church tradition, or other explicit sources, are silent, the underlying thought behind the question can surprisingly be answered mathematically. Paul, like everyone, had 2 parents, 4 grandparents, 8 great grandparents etc. A thousand years before his time he would have had around a billion ancestors, far more than the population of the whole world. This means that if Jonathan's line had not died out completely, then he would have been an ancestor, many times over, of every Jew then living.
Either no first century Jew was descended from Jonathan, or every first century Jew was descended from Jonathan. If this is so, then the direct saving of Paul, in particular, cannot have been a particular fulfilment of David and Jonathan's covenant, appealing as the idea seems.
This article from National Geographic looking at the European population over the 2nd millennium AD, rather than the much smaller Jewish population in the first millennium BC, concludes:
The most recent common ancestor of every European today (except for recent immigrants to the Continent) was someone who lived in Europe in the surprisingly recent pastβonly about 600 years ago. In other words, all Europeans alive today have among their ancestors the same man or woman who lived around 1400. Before that date, according to Changβs model, the number of ancestors common to all Europeans today increased, until, about a thousand years ago, a peculiar situation prevailed: 20 per cent of the adult Europeans alive in 1000 would turn out to be the ancestors of no one living today (that is, they had no children or all their descendants eventually died childless); each of the remaining 80 per cent would turn out to be a direct ancestor of every European living today.
To misquote2 Corinthians 11 22; if Paul was descended from Jonathan so was everyone else.
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I'm not sure if this question has arisen in Christendom. As, most of Christendom is fascinated by Moses, King David, Jesus, Peter, and Paul. I'd say it's 'unlikely' but...there are billions who have gone before us. :) I'm sure it's come up before but I'm not sure that the question has been documented.
As to the question itself. My current understanding is no jew desired to keep a detailed tally of their heritage, with exception to the descendants of David (Luke 2:4) since they were ancient jews, it was their conviction that the Messiah would come through the line of David (2 Samuel 7:12-16). The only identification they, all Israelites, used are two fold. Whom was their parent and what tribe did they come from? As you can see this thread throughout scripture.
If you want a lot of these examples, go here.
In conclusion, someone throughout the ages could've asked this same question but I haven't seen it yet. Also, the jews simply wouldn't ask this question because they were focused on the Davidic line to find the Messiah.