Well, He was easier on the Roman legionaries than on His own folks.
“Walking the extra mile” originally meant willingly accepted being ordered around by Romans.
The Romans seemed to be ok with Him; though the bad juju between them and Jews was thick enough to breathe, the centurion respected Him enough, despite his need, not to ask that He defile Himself by going to his home. This from a people who were legally entitled to order everybody around.
As I mentioned, there were no legionaries in Judaea or the Galilee in the 30s. Pilate’s soldiers were auxiliaries conscripted from the (non-Jewish) natives like Samaritans, and Herod Antipas had his own army - also mainly drawn from locals.
And as I said, the centurion/ was likely
not Roman, even though we assume that he is because of his title. It would have been a Herodian soldier working for Antipas. First, we know that Herod the Great copied the Roman military structure for his own army, and it’s likely his sons did so for their own armies. So it’s not unlikely that there would be a ‘centurion’ in the Herods’ army. Second, unless there was an emergency, Roman soldiers had no business being in the Galilee, which was under Antipas’ rule, much less in a small village like Capernaum. In fact, there would be no Roman presence in Capernaum until well after the time of Jesus. In His day it was just a small, rural Jewish village. It’s very telling IMO that John’s analogue to the story of the centurion is the story of the
basilikos, the “royal official.”
“Love your enemies” and “turning the other cheek” is commonly explained nowadays in terms of Roman soldiers, yes - love the Romans, turn the other cheek and walk the extra mile even when they bully you.
But as I’ve said in some other places, aside from the fact that the Romans would have actually more likely been invisible in the Galilee contrary to what some modern scholars like to think (they would have had certainly no presence in the rural areas, and Jesus was mainly addressing rural Galileans when He said these words!), we don’t really have that firm evidence that Roman soldiers actually did the stuff modern movies like to claim they did: roam the countryside and impose fear on the hearts of the Jewish natives by randomly crucifying them or setting fire to their houses or making them do forced labor.
In reality, they probably never did that, certainly not in Antipas’ tetrarchy (where they are absent) and not even in Judaea Province. The Romans governed Judaea Province via indirect rule: the Roman governor is nominally in charge, but in reality, local Jewish magistrates ran the government on his behalf. That’s actually pretty much why it was the chief priests and the Temple police that arrested Jesus. It was technically
their job to do so on behalf of the prefect. They would arrest Him, examine Him, then hand Him over to Pilate to be sentenced, since
he was the one that had the right to execute.
So my opinion is that unlike the modern assumption, Jesus or His original audience did not specifically have in mind Roman soldiers when He said “turn the other cheek” or “go two miles when told to go one mile.” Who knows? Maybe the ‘enemy’ was the village magistrate or that snobby rich guy in your area.
Personally, I’d point to these stuff more as Jesus being okay with Antipas’ guys (even though Antipas himself purportedly sought to kill Him once): I mean Chuza and his wife Joanna, Matthew (since he was a tax collector in the Galilee he would have been working for Antipas rather than the Roman governor), this centurion/royal official.
Even Pilate sought an excuse to let Him breathe, though lacking the courage to stand up to the masses.
I’ll admit, given what we know about Pilate from the extrabiblical sources (Philo and Josephus), I won’t say that he ‘lacked courage.’ I won’t go as far as those modern historians who say Pilate was a total monster who butchered Jews for the fun of it and the gospel accounts of Jesus’ trial before him is mostly fictional (because how can such a heartless villain be so indecisive?

), but I don’t really buy the weak, vacillating image of Pilate folks often glean from the gospels.
The gospels have their own reasons for portraying Pilate the way they do, just as Philo and Josephus have their own motives for portraying Pilate the way they do. The actual historical truth must be somewhere in between those. Instead of seeing the gospels’ Pilate as being weak-willed, I see him more as being shrewd. I mean, this was the guy who wrote ‘King of the Jews’ as Jesus’ crime, and the guy who lasted ten years as prefect of Judaea.
Personally,
I agree with this assessment (
and this) and think that there might have even been some kind of play-acting going on when Pilate was trying to ‘release’ Jesus.
For that place and time, I’d say He got on remarkably with the Romans (until everybody ganged up on Him).
Well, Jesus’ only verifiable actual contact with Romans was when He showed up before Pilate and was crucified. Maybe He might have perked up their ears when He was in Judaea for the festivals as is written in John, but for a good deal of His life, He might not have had any close contact with them. The Galilee was not occupied by the Romans, it’s extremely unlikely that he encountered Roman soldiers there, and even in Judaea the Romans did not always show up. They’re just a sort of invisible presence. Think something like Sauron in
The Lord of the Rings (the books); he’s nominally the big bad, but he doesn’t appear directly in the story.