A battle was fought in the Thrugii asteroid belt during the Clone Wars. During the battle, future Imperial Grand Admiral Thrawn met and fought alongside Jedi General Anakin Skywalker to know if the Galactic Republic would be a suitable ally for the Chiss Ascendancy. Though the battle ended with the victory for the Jedi and for the Republic, Thrawn concluded the Republic was a poor ally for the Chiss Ascendancy.
In face of a mysterious threat at the Unknown Regions, the Chiss Ascendancy desired to know if the Galactic Republic, located at the Outer Rim Territories, would be a suitable ally for them to fight against that threat. As such, they assigned the Chiss Thrawn to explore the Outer Rim of the galaxy.
Once at the Thrugii asteroid belt, Thrawn met the Jedi General Anakin Skywalker, who was fighting a battle there. Deciding to help, Thrawn joined Skywalker in the battle and fought alongside him. Ultimately, the battle ended with the victory for the Jedi and the Republic.
Thrawn found himself impressed with Skywalker's cunning and courage, while in the other hand, Skywalker became impressed with Thrawn, speaking highly of him to Supreme Chancellor Sheev Palpatine upon returning to Coruscant.
Unfortunately, Thrawn found himself unimpressed with the state of the Republic, however. As he decided to resume his travels, Thrawn had already decided that the Republic would be an unfit ally for the Chiss Ascendancy: Its democratic style of government, in his opinion, created a bogged down system where everyone had a voice but nothing was accomplished.