On second thought, re the ask I just sent, maybe Katsura just likes to eat for free and sleep in peace for a few days, and that's why he can be so nonchalant about getting caught - as he's so good at breaking out of jail again. Might not be anything deeper than that...
The 'liking free food and shelter' thing does sound like a practical reason for Katsura yeah, but because I like reading deep into Gintama... hope you don't mind some long rambly paragraphs XD
I personally think it serves to further show a character parallel between him and Shouyou - or rather, the distinctive way in which they're different. To me, the main thing that sets Katsura apart from Takasugi, Gintoki and Shouyou is that, of the ShouSon, he is arguably the one who was most able to 'balance' all the different parts of himself. His 'Runaway Kotarou' identity and his 'Noble Youth of Madness' identity, his identity as a samurai of that time period (and all that it entailed with regards to dying with honour) and the last of his line. Katsura doesn't get nearly as many scenes as Takasugi and Gintoki do with Shouyou, but I do think that's on purpose. Katsura's quiet strength is not just his endurance, but how comfortable he is with being 'flexible'. Sakamoto pointed it out - being the 'Runaway' is not just having the ability to endure people jeering you as you run to live another day, it is having the wits to survive, the wisdom to know which way truly is a 'death trap', to keep yourself and others around and fighting for the long haul. It is to keep both your own and others' wellbeing in mind. Katsura showed the ability to balance 'being true to one's own self' while not being so 'rigid' that he broke when change had to come. It's a feat of a kind of endurance that I think contrasts Shouyou/Utsuro in a unique way. In my notes on Lesson 667, I noted that Gintoki and Utsuro seem set up as the ‘Indestructable/Immortal and Indomitable’ - but Katsura is also part of this as well. Katsura has his own association with pine trees, 'coming back from the dead' in Benizakura, returning over and over to keep the Joui fight from truly dying, and most importantly - adapting, learning and growing. Where Takasugi and Gintoki are still quite tied up in Cliff Day, Katsura silently processes it and is able to step away from it in a cleaner, healthier way. I've mentioned before that I think this is why Katsura is whom Shouyou calls 'a genius'. Shouyou, whom I've talked about as 'not quite being able to escape his own/society's prison' - so by contrast, Katsura can. Katsura, Takasugi and Gintoki all are shown to leave a physical prison at some point in the series, but arguably Gintoki and Takasugi end up in those prisons for 'bad' reasons (suicidality, wanting to punish themselves, being punished by the Shogunate etc.). Katsura, like you say, shows an almost whimsical attitude in Vol 68. IMO the narrative sort of demonstrates a uniqueness in Kastura's... I suppose comfort? in being 'caught' - because he possesses what Shouyou was talking about - he is demonstrating that he is 'truly free'. The bars of the prisons he is put in (mental or otherwise) can't and don't really hold him, no matter who puts him there or whether he walks into it of his own volition. Not because he is necessarily 'good' at jailbreaking (who could have predicted half the things that happened to lead him to be able to break free?), but his sheer belief that he will do so. If anything, I think any 'subconscious drive' he may have had would be in being able to have a confidence that he will endure - that he will persevere, and not lose sight of himself no matter what happens. That this prison, too, will not be able to hold him. (I kind of want to talk a bit about how this connects to Gintama's sub-theme around 'shame' but this is already very long - Katsura is one of the true Beach Samurai.)
I think he would have loved being able to keep his teacher company if he couldn't free him, like Nobume did...
This is probably where my thoughts might be a bit different to the mainstream, but I think Katsura... wouldn't?
Now, don't get me wrong, I don't think Katsura loved his teacher any less.
But I also think Takasugi and Gintoki allowed their love for Shouyou to consume them and destroy them almost completely, which when you think about it, is not a very healthy way to be. It's more to do with the 'balance' I think Katsura has that I was talking about above.
Love is wonderful, but loss is also part of life, and Gintama doesn't shy away from it. In fact, I would argue that one of its strengths is showing its characters explore how they navigate the grief after loss.
I think Katsura would have the ability to remember his self (his whole self - the self that knows he embodies his grandmother, his parents, his family line, that he is also a leader to the Joui, that he is a friend to others, that he is more than just one relationship to one person, no matter how important that relationship is to him.)
I think that he would gladly walk into that prison cell and sit with Shouyou and pour him a drink and chat... but also he would be the most likely to know not to stay there. (Shouyou being unable to leave the prison not because noone set him free, but because that is where Shouyou chooses to stay. Metaphor for the past, unhealthy mindsets, etc etc.) Which, I think, is where Gintoki would struggle and Takasugi will probably just fail.
ETA: I forgot to add - I think also that TakaGinZura being put in 'prison positions' is interesting from a 'character growth' position. They are leaders, but one of the important themes in Gintama is the ‘there is something to relate to in everyone’ theme brought up in the Kappa chapter. As someone who desires to change Japan, I think it says something that Katsura doesn't just look at the top of the chain of command/deals with the Shogunate, but he also looks at the 'middle' (the everyday people of Edo) and is (enthusiastically) willing to visit the 'bottom' (the prisoners, those at the bottom of society). One could read it as Katsura willingly going out to build a holistic view of his society, comprehensive as he could get it. Contrast that a bit with Takasugi insisting on his own autonomy while being puppeted his traumas, and Gintoki's struggle between... so much. Katsura's path is in a way closer to Sakamoto's, once Gintoki has set him straight when they reunite again.









