What I think I hated about it was that its a waste. Even with all the atrocities the party was able to commit, they went so far as to waste what was otherwise a good, dedicated life.
They put the resources into him to kill him. Where was the payoff? Its impractical, its a waste. Nobody was supposed to know he was reformed, so its not soul crushing to any character in the book, only you and possibly those working directly with him. It wasnt a public execution. And the kicker is his death caused zero ripples. iirc they even found a use for the female protagonist after her own reformation.
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Its something I was never able to fully cast aside when reading about some of histories figures. The waste of life. Objectively, it irks me.
There's quite a difference between executing someone while they are still defiant, and brainwashing them, forcing them to repent, and then setting them free, with the promise of eventual execution.
As for why The Party goes through all of that trouble, remember: The Party does
not like to lose. Any bad thing that happens was predicted to be much worse, no, really, you can go and read about it in the back issues of the newspapers. If a rebel dies defiant, he has a final minor victory, the knowledge that they can't do anything worse to him. When you make him love Big Brother before he dies, he's lost that last spark of defiance. He
loses.
Also, it's worth pointing out that there may be many others like Winston, with the slightest scrap of defiance just waiting to get out. If that one guy, you know, that skinny guy who works at MiniTruth, if he starts acting funny and all of a sudden becomes a clerical error, all those others who might dissent will mark it as what might happen to them, and then they'll want to do something. But if he becomes one of the millions of perfect citizens out there, no-one's going to notice when he's the newest unperson on record. And wait... why would The Party want to kill a perfect citizen? They wouldn't, right? Maybe he really
didn't exist and I'm imagining it.
I dunno. This is all a big WMG.