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Following is the speculation from the footnotes of the NAB.

I would hesitate to place too literalistic an emphasis on the word 'all'. Don't we also read that 'all' Jerusalem came out to be baptized by John the Baptist? Did 'all' include every single person in Jerusalem?

5 [17] Matthew is concerned with fourteen generations, probably because fourteen is the numerical value of the Hebrew letters forming the name of David. In the second section of the genealogy (Matthew 1:6b-11), three kings of Judah, Ahaziah, Joash, and Amaziah, have been omitted (see 1 Chron 3:11-12), so that there are fourteen generations in that section. Yet the third (Matthew 1:12-16) apparently has only thirteen. Since Matthew here emphasizes that each section has fourteen, it is unlikely that the thirteen of the last was due to his oversight. Some scholars suggest that Jesus who is called the Messiah (Matthew 1:16b) doubles the final member of the chain: Jesus, born within the family of David, opens up the new age as Messiah, so that in fact there are fourteen generations in the third section. This is perhaps too subtle, and the hypothesis of a slip not on the part of Matthew but of a later scribe seems likely.