Well before Thrawn’s career within the Imperial Navy in the Galactic Empire, the Chiss came
across the Republic General Anakin Skywalker during the final year of the Clone Wars.
Their paths intertwined when they both found themselves on the far edged, Outer rim planet
named Batuu; where they both helped one another to recon and eliminate the threat of a secret
Separatist project for their separate, respective missions.
During this time, Thrawn and Anakin came to highly respect each other for their unique
skill sets.
Anakin was the first Jedi Thrawn had ever met in person, having only heard about the
magical force wielding knights in rumors and tales.
He also came to value the Jedi’s courage and fighting prowse, so much so that Thrawn
went out of his way to help Anakin even after he had already completed his own mission for
the Chiss people.
On the other hand, Anakin came to have high regards to Thrawn for his tactical mind and
nearly unnatural ability to analyse situations.
He was so impressed with the Chiss’ talents that Anakin actually mentioned and praised
him to Chancellor Palpatine after he returned back to Coruscant.
Many years later, Thrawn used this interaction between the two and Anakin’s earlier praise
of him as a means to gain Emperor Palpatine’s trust.
However during this same meeting Thrawn was informed that Anakin was killed during the
Clone Wars, a statement the Chiss seemed to be skeptical of.
It wouldn’t be until much later in his career, finally at the rank of Grand Admiral, that
Thrawn would get the chance to work alongside Darth Vader.
Palpatine had felt a disturbance in the force that came from the planet Batuu, in which
he decided to send his Chiss Grand Admiral and Sith apprentice to go investigate.
During their trip, Thrawn on multiple occasions tested, and in some ways, trolled Darth Vader
on the fact that he was the very same Anakin Skywalker he had worked alongside with many
years earlier during the clone wars, and ironically they were heading back to the very same planet
they originally met on.
As we all know Vader regarded Anakin to be a separate person from himself, someone who
had died the moment he became a true Sith Lord.
Any memories of his past brought about him tremendous emotional pain, and it was so bad
for him that he literally killed all those who discovered his true past identity.
And Thrawn’s trolling or tests almost ended up getting him force choked, especially as
they got gradually more irritating for the Sith Lord.
At first during their journey to Batuu, Thrawn often brought up Anakin and his adventures
with the Jedi Knight whenever talking about what he knew about the planet they were about
to visit.
Each time Anakin was brought up, Vader always made it clear that he was dead and of no importance,
to which Thrawn always responded with “so I have been told”, never fully acknowledging
the Sith Lord’s statement to be true.
When this first happened, Vader wasn’t fully sure if Thrawn was mocking him or if that
was just how he went about himself.
Each time he checked the Grand Admiral’s emotions through the force to see if that
was the case, only to find that Thrawn was always fully neutral whenever he indirectly
dismissed Vader’s claims that Anakin was dead.
As they arrived to Batuu and began to explore it, Thrawn began to talk about the planet
with Vader as if the Sith Lord had been there with him on it long ago, even once using the
word “we” when talking about how he discovered vital intel on it.
When this happened, Vader actually had to take a moment to stop himself before correcting
the Grand Admiral that no one else on the Star Destroyer had ever visited that planet.
Thrawn apologized, stating that it was true that only he himself ever visited the planet,
and that he made an error by saying “we” when referring to how he discovered the information
during his visit at the time of the clone wars.
Just like last time, Vader checked Thrawn’s emotions through the force only to again find
that they were neutral just as they were the last confrontation.
Though perhaps the biggest troll move from Thrawn was what came next.
The so called disturbance that Palpatine felt came from a small group of Chiss children
who had been kidnapped by a violent alien species that came from the Unknown Regions.
These Chiss children were in fact force sensitive, and Thrawn’s people used their connection
to the force as a means to navigate through the dangerous portions of the Unknown Regions,
as the children could use the force to show them safe passages through hyperspace.
They also used a special machine to better help them see the paths through the force
and submit them to the ship they were on.
During their search of another kidnapped group of force sensitive Chiss children, Thrawn
suggested Vader to use this machine and the force to better locate the kidnappers that
were within deep space of the Unknown Regions.
Vader reluctantly agreed to this and entered the machine.
Once inside, Thrawn asked if he wanted to know what his people called those who used
the force to navigate space travel?
Vader didn’t seem to care, but Thrawn continued on, first saying the name in his native language,
before translating it to Galactic Standard, which translated to Skywalkers.
This of course grabbed Vader’s attention, in that Thrawn purposely asked him to enter
this machine and later go out of his way to inform him that those who used it were called
Skywalkers.
Again through the force Vader checked Thrawn’s feelings, and once more they were neutral.
This only frustrated the Sith Lord, which only piled on Vader’s dislike toward the
Grand Admiral as he had suspicions of Thrawn’s true loyalty to the Empire throughout their
time working together.
There would be one more time after that where Thrawn hinted he knew Vader was Anakin right
in front of him, by stating that he felt he owed Vader a favor because many years ago
Anakin had helped him while they were on Batuu.
And that he wanted to balance that out among the two of them.
At a point where he was almost shouting, Vader stated he did not care whatsoever about any
favors that Thrawn believed he owed and that Anakin was dead, that he did not matter.
That Thrawn’s only concern should be serving to Empire, and not to any other man or purpose.
Not out of fear, but perhaps out of realization that Vader was truly not the same man as Anakin.
Not in a literal sense, but in a mental one.
And that the Jedi Knight he served with and befriended many years ago was never going
to return.
As for the very first time, Thrawn acknowledged in front of Vader that Anakin was indeed dead,
and that he made a mistake of ever assuming that wasn’t the case.
After that, Thrawn made no mention of Anakin or any means to try to bring the Jedi back
from Vader’s mental imprisonment.