'Draco was bully, how could you ship him with Harry!'
As a reader, my main reaction to Draco as Harry’s supposed peer rival is frustration. The dynamic doesn’t really work for me because the contest is never fair. Draco is so thoroughly outmatched, in so many directions at once, that Harry has effectively beaten him across the board before the 'bullying' even has room to breathe.
Whatever prestige Draco tries to claim through the Malfoy name simply can’t compete with Harry’s standing in the wizarding world. From the very first book, it’s obvious that Malfoy influence doesn’t rival the automatic goodwill, protection, and indulgence Harry receives just for existing. Draco expects his status to earn him special treatment like an exemption from the rule banning first-years from owning broomsticks and it doesn’t. Harry, meanwhile, not only gets the rule bent, he has a broom bought for him outright. And even the idea that Harry might be disadvantaged by poverty collapses almost immediately, he isn’t a poor orphan at all, but an extremely wealthy one.
Institutionally, the gap only widens. At Hogwarts, Harry gains Dumbledore as a mentor, with McGonagall and Hagrid repeatedly stepping in to guide and protect him. Draco gets…Snape. And Snape, despite his favouritism, spends a remarkable amount of time ensuring Harry’s safety.
The Malfoy fortune doesn’t close the distance either. Harry consistently comes out ahead in the escalating broom rivalry, and even when Draco briefly has the superior broom in CoS, he still loses. All of Draco’s years of Quidditch practice amount to very little; Harry openly admits Draco is skilled, but Harry is simply better. Natural talent wins.
Nor does Malfoy influence actually pay off in the long run. Lucius manages to remove Dumbledore from power temporarily, but ends up expelled from the Board of Governors himself. The greatest victory Draco ever achieves through that influence is Buckbeak’s sentence. He can’t get rid of Hagrid, not even by exposing him as a half-giant. All he manages is targeting one of Hagrid’s animals—and even then, Buckbeak ultimately escapes.
If we assume the Malfoys are politically cunning, that could have benefited Draco. But it also requires assuming Draco never follows his father’s advice. He’s told to conceal his hatred of Harry and immediately announces it to the entire school. He’s advised to keep a low profile during the basilisk attacks and instead loudly gloats, making himself look suspicious. It’s hard to imagine Lucius being pleased with Draco’s refusal to show public support for Harry at the end of GoF, or worse, his mocking of Cedric Diggory’s death on the train.
Being sorted into Slytherin implies a degree of cunning, but Draco rarely demonstrates it. His midnight duel scheme in the first book is clever enough; everything after that is a steady decline. His attempts to get Harry in trouble consistently fail. When he spies on the Trio, he’s caught. When he tries to turn public opinion against Harry, it never sticks. The Dementor disguise plan is especially ridiculous, how anyone thought that wouldn’t end in punishment and lost House points is beyond me. Even when Draco is technically right, as in PoA when Harry is in Hogsmeade without permission, reporting him gains Draco nothing because Lupin intervenes.
The only times Draco manages even minor success against Harry are when an experienced adult is backing him. In Book Four, Rita Skeeter does the heavy lifting. In Book Two, he gains the upper hand in the Duelling Club only because Snape intervenes. Even then, Harry’s adult allies far outweigh Draco’s. Left on his own, Draco’s main accomplishment is bullying Neville in the corridors.
Draco doesn’t seem to have real strengths or lasting advantages—and he doesn’t even appear comfortable with the ones he’s supposed to have. When accused in CoS of buying his way onto the Quidditch team, a very Slytherin thing to do, his reaction isn’t smug pride but embarrassed rage.
Despite common assumptions, I also don’t think Draco is especially popular. Flint protects him, Crabbe and Goyle stick with him, and Pansy clearly cares about him—but that doesn’t make him a leader. His own year lacks anyone strong enough to challenge him, but the wider House doesn’t rally behind him. They laugh at his jokes, but when it matters like at the end of GoF they don’t follow his lead at all. Slytherin stands for Harry at Dumbledore’s banquet. Only Crabbe and Goyle stay seated with Draco.
When Lucius is sent to Azkaban, that pattern repeats. Only Crabbe and Goyle accompany Draco when he attacks Harry on the train in revenge. The attempt ends with Dumbledore’s Army defending Harry and leaving Draco and his friends hexed and humiliated another point in Harry’s favour when it comes to popularity.
Draco is also a coward, both in moments of immediate danger, Quirrell in Book One, Buckbeak in Book Three and in his emotional resilience. He doesn’t recover well from trauma; after Fake Moody turns him into a ferret, even hearing the man’s name unsettles him. He’s volatile, quick to anger, and prone to speaking when he shouldn’t. He dishes out insults easily, but can’t tolerate them in return.
When we see Draco without his usual performance for Harry—like in Knockturn Alley or during the Polyjuice Potion scene in CoS—he comes across as petulant, sulky, and whiny. Despite the narrative’s attempts to parallel him with Snape, his tone in these moments doesn’t resemble Snape’s at all. If anything, he sounds more like Peter Pettigrew, whose whining submissiveness toward Voldemort in GoF feels strikingly similar to Draco’s behavior when he doesn’t know Harry is watching.
And yet, alot of people including myself love Draco Malfoy.
Draco’s most endearing trait is that even though he never wins and he never quits.
He keeps showing up. He keeps trying. He keeps positioning himself opposite Harry, even after every prior encounter has proven this is a fight he cannot win. There’s something deeply human in that persistence. How do you fully hate someone like that?
Somehow, Harry consistently sees him as someone worth opposing. For all that Draco loses, Harry keeps engaging with him. He keeps responding. He keeps fighting back. On some level, Harry consistently gives Draco exactly what he wants: attention. Harry does not ignore Draco the way he ignores lesser irritants. He doesn’t dismiss him as irrelevant. He rises to the bait, trades insults, watches him closely, and treats him as someone worth opposing.
Then, in HBP, the dynamic quietly flips. For once, Draco isn’t obsessively trying to get Harry’s attention and he withdraws. He becomes secretive.
Even when everyone tells him he’s wrong, Harry follows his instinct all the way to its (correct) conclusion: Draco is a Death Eater. On some level, Harry understands Draco better than his friends do. He recognizes that something has gone catastrophically wrong, only because for once Draco’s attention isn’t fixed on him at all.
So to answer why I ship Draco with Harry even if he's a 'bully' is that because Draco is relentlessly, singularly obsessed with Harry from their first meeting onwards, Harry never stops engaging, their rivalry is mutual rather than one-sided. I find them entertaining, it fun to watch them knowing that there is no danger for our protagonist here.