B.Q. Book Two: Black Princess Ascendant

Chapter 12: Sweet, Sweet Freedom

J.K.'s explanation for James being Head Boy despite not being a prefect, at least according to the wiki, is that the Headmaster can choose whomever he wishes for the position. That policy doesn't make any sense to me, but there you go. How James finally convinced Lily to give him the time of day is not explained in canon, but my guess? The same way Ron got with Hermione: magic-induced stupidity, love potions, authorial fiat, take your pick.

Disclaimer: Did Hogwarts employ both a caretaker and a groundskeeper, even though those tasks were likely taken care of by the castle's house-elf population? If so, I don't own the Harry Potter franchise; it belongs to J.K. Rowling, Scholastic Press, Warner Bros., and whoever else she sold the rights to.
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A series of cracks echoed through the silent forest, and the Dark Lord Voldemort, accompanied by four of his Death Eaters, appeared on a road of packed earth. Pointing to a copse of trees to one side, he ordered, "Get behind cover, disillusionment charms as well. We do not want to be seen."

The men did as they were told, though it was clear they were anything but pleased by his command. "My lord," Timothy Nott began tentatively once they were hidden, "far be it from me to criticize—"

"Just spit it out," Voldemort interrupted with an unseen roll of his eyes. Damn Notts never can get to the bloody point. His father is the exact same way.

There was a rustling behind him as his follower shuffled in place. "Very well, my lord. Why are we waiting in these woods when we could easily take on anyone who tries to stand in our way?"

"And here I thought you were intelligent." The wizard spluttered at that, and the others barely contained their snickers. "Tell me, can you defeat the entire DMLE all by yourselves?"

"Certainly not, my lord. It would require the kind of power possessed only by you to do such a thing."

Is he just pandering again, or does he truly believe I can take on over a hundred wizards in a straight fight? He shook his head. This was, unfortunately, not an uncommon mindset in Death Eaters whose parents had also served him; them being raised to think he was invincible was an advantage, especially now that he had proven that not even death could truly defeat him, but it also meant they expected even more miraculous feats of magic. He might be the most powerful wizard since Merlin, but even so, he would have trouble against those odds. Then again, there's a reason I chose to wage a guerrilla war against the Ministry rather than a full frontal assault. A hundred foes at once would be difficult, but ten groups of ten? Child's play.

Pulling back from his introspection, he replied, "But why fight more enemies than is necessary? We are not the boorish Light that answers each challenge with a headlong charge. We are cunning, and if the opportunity to sneak past the opposition presents itself..."

He raised his left hand to bid them be silent, and a tap on his head caused him to become invisible as well. A contingent of navy-robed mages, over a dozen strong, appeared from around a corner, and they all Disapparated as soon as they passed the Death Eaters' position. Another rap of his wand let him fade back into view. "...we take full advantage of our enemies' mistakes. Follow."

The five Dark wizards jogged down the road in the direction from whence the DMLE wizards had come, and Voldemort could not stop the fierce smile that appeared on his face as the dock came into view. This mission felt unexpectedly similar to his earliest raids, when he was less a general giving orders from his war room and more a squad commander leading his servants into battle personally. The rush as he stormed the enemy's stronghold, his magic singing in his veins as he prepared to deliver death upon them, the anticipation of being forced to create plans on the fly...