A Goodreads user asked this question about The Bear and the Dragon (John Clark, #3; Jack Ryan Universe, #11):
This is going to be my first Tom Clancy novel I have read. From the reviews I see that the book isn't too good. Should I start Tom Clancy novels with another book?
Jonathan Nearly all the characters are recycled from previous books. He tries to cram 25 different featured characters together with virtually no character dev…moreNearly all the characters are recycled from previous books. He tries to cram 25 different featured characters together with virtually no character development. If you read it first you'll get the impression that Clancy is just a shallow writer who leans on lazy stereotypes and political tropes.

I'd definitely recommend "Hunt for Red October" as a first read, or "Red Storm Rising" if you prefer the large-scale war story. If you read Clancy's good books first then at least you'll have a more nuanced view of him as a writer before you get to the poorly written stuff.(less)
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