Worst Trek novel by far is "The Laertian Gamble". "Before Dishonor" is way better than LG.
At least The Laertian Gamble is still Star Trek. For pretty much every other published Star Trek novel, at least you can't deny that they are science fiction novels featuring the characters, settings, set pieces, and/or themes of the Star Trek universe to some relevant degree. The worst Trek novel I've ever read has to be
Shadow Lord, because it had nothing at all to do with Star Trek in any way that mattered narratively or thematically.
Also its cover has one of the worst representations of Sulu I've ever seen.
Laertian Gamble took plot line of the episode
Rivals, dealing with the good luck/bad luck neutrino machine changer, and just turned it into a really odd and stupid thing (as I recall in the end of LG, the characters were even adding a kitchen sink to the device they were trying to make). At least with
Rivals it was confined to the station, and seemed to have had some thought put into the device.
Laertian Gambit went from being science-fiction to a pure fantasy novel at the end.
Not to mention, but with 72 Chapters within a 280-300 page book, the chapters barely managed to get anything going. Some chapters were only half-a-page in length! It would be like:
Chapter 20
Odo stepped out of the turbolift and started walking down the corridor.
Chapter 21
Some deputies were struggling with one of the merchants.
Chapter 22
"What's going on here", Odo asked.
The editing of the book was really terrible, and really needed a lot more work.
As far as
Shadow Lord goes, I've never read it. As far as characters on covers, I always thought that the artist of
Chrysalis did a fairly poor job of Harry Kim's face.