In the last issue with Tom Mandrake as series artist, Gaunt learned a rather disturbing fact: Death was not going to be the end for him. His unwillingness to abandon a friend had far-reaching consequences, and the last third of the series starts to explore that.
Set 200 years later, GrimJack is a man named Jim Twilley, but he's also John Gaunt, whose fate is now tied to Cynosure's, condemning him to be reborn so long as the city exists. He takes it well. That's a lie, he takes it horribly, initially refusing to try and reconcile two sets of lived experiences. once he remembers his past, he goes out of his way to claim that Jim Twilley doesn't exist, his family and friends remember someone who doesn't exist. He eventually pulls his head from his ass, but as usual, his decisions had consequences.
This version of GrimJack is wilder, more vicious than his earlier incarnation. Which is saying something given what that guy got up to, but it's true. He has less control of his worst tendencies, or more likely he doesn't bother to control them. Learning that you're a long way from ever getting back to your loved ones in Heaven will do that to ya. In his previous life, he knew how to bargain with people, how to at least attempt to sweet-talk someone. Now he doesn't even try. Even when people agree to help him or extend a helping hand, he goes out of his way to push until he pisses them off. His best friend BlacJacMac made allowance for him if he did return, GrimJack burns that bridge down in one issue.
I think the first third of GrimJack (roughly the Truman and Tom Sutton issues) is about how Gaunt how Gaunt's stubbornness and loyalty lead to him standing by his friends and they, in turn, stand by him. The second third (Mandrake's run) highlighted how that, stubbornness and loyalty can go awry for his friends. The final third seems to highlight that GrimJack is his own worst enemy. He grows more reckless and desperate as it progresses, the faint hope of what he might get back to someday failing to keep him going.
All his attempts to improve his lot, or even to help save a long-lost friend, end up failing because he can't put his own selfish desires aside. He can't let what Major Lash did pass, which would have let him stay dead. Instead, he takes revenge and ensures he'll have to deal with him again, and again. So that when he does finish it, he puts everything else he was trying to accomplish at risk. As he can't seem to find any pleasure in anything other than tormenting people or taking revenge, he just keeps pissing different people off until he's besieged from all sides. All the times he just had to have it his way coming back to haunt him. Not even in any coordinated, "super-villain team-up" manner, just all these people deciding, "fuck it, I'm sick of that asshole," at the same time.
(There's a series of back-up stories that run near the end that detail Gaunt's life growing up, and what happened between him and his brothers. The main thing is we learn that is was impressed on John very early in life that he should never allow anyone to disrespect or harm him. Every injury must be repaid in kind, or worse. He never unlearned that lesson.)
Flint Henry's GrimJack is different, and not just because it's an entirely different physical body. His version is more expressive, less guarded. Truman and Mandrake's GrimJack has a death's head grin that suggests a cold enjoyment of the fact they're about to kill an enemy. Henry's is wilder, like he's either not even aware of what he's about to do, or he's planning to go a lot further than just killing. And Henry is more graphic with the violence. When GrimJack cuts somebody apart, there's blood and guts following the arc the sword.
The whole run looks more, I'd almost say lurid. The closest thing Twilley gets to a romantic relationship in this run (minus some time travel hijinks) is with a sorceress who draws off tantric energy. So, you know, a fair amount of implied fucking to charge her engine. The colors are brighter, the oppressive shadows of Mandrake's run largely banished. Henry's version of Cynosure is the most crowded, the most hi-tech. It feels like it owes more to Blade Runner or sci-fi of that sort, whereas Truman's ran more to noir and Mandrake's to horror or German Expressionism, maybe. It is 200 years into the future, so that makes some sense, though I'd also expect there to be dimensions coming into phase that time runs backwards, or it moves faster and civilizations have been destroyed.
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