Grand Admiral Thrawn vs Star Trek

[Shai-Hulud]

Grand Admiral Thrawn vs a council of five consisting of Kirk, Sisko, Picard, Solok (DS9), and Khan (TOS).

Each side gets a fleet of equivalent ships and crew.

Strategy is planned out for a week, then fleets move into contested space at opposite ends.

[Shai-Hulud]

For specificity's sake, let's revise the OP a bit.

In addition to both sides getting equivalent ships and crew with which they are both equally familiar, let's fill in some blanks.

Let's say the ships and crew are a midway point between Starfleet and Imperial. So in all respects the difference is split, and both sides will find an equal number of things familiar and different.

Let's also say that both sides get a full six months of prep. This includes both holodeck simulations and actual, physical drills.

So, equivalent ships and crew with which they are both equally familiar.

[The MunchKING]

Assuming Zahn Thrawn, there are 2 answers:

Joke answer: Star trek Humans' complete lack of Pop-culture since the 1920s saves the day, as they have no art for Thrawn to study and understand!

More-Serious answer: All five of the Captains had fairly straightforward personality archetypes. Most of them would be pretty easy to predict, and Star Trek tactics in general weren't great... So Thrawn probably has an advantage.

[master of read]

they all go down to thrawn smooth, sexy voice.