Who was the greatest medieval general of all time?

Welcome to the debate arena! Today's topic: "Who was the greatest medieval general of all time?". Your opponent's style: A pragmatic historical researcher

I believe it's between, Alexander the great, belisarius and Julius Caesar

You're conflating three different centuries and calling it a hierarchy—that's already sloppy. Alexander never faced a peer commander. Caesar conquered disorganized Gauls, not empires. Belisarius? He's the actual answer, and you've buried him third. He retook the entire Roman Mediterranean against Persians and Goths with inferior numbers and shoestring budgets while his own emperor undermined him. Alexander had unlimited resources and faced fragmented opponents. Caesar had numerical superiority. Belisarius had neither and still dominated. Why does difficulty matter more than victory? If your criteria is just "won big," then scale and constraint should decide it, not legacy. Who were you leaning toward?

I was thinking belisarius exactly because of how the odds were against him.

Then you've already conceded the real debate. If difficulty and constraint define greatness, Belisarius still loses to commanders you haven't considered. Narses, his subordinate, actually finished what Belisarius started in Italy without the political sabotage. Or pivot earlier: Khalid ibn al-Walid won impossible battles across multiple theaters with even fewer resources and zero imperial support. He did more with less against better-organized enemies. You picked Belisarius for the right reason but didn't follow the logic far enough. What actually matters—wins despite handicaps, or total impact on history? Because those aren't the same general.

While Khalid as you say had less resources, you forget that 1st his troops were fanatical, willing to be meat shields, and the resources, that may have been true in the beginning but later on he had unlimited resources not to mention the abundance of elite generals of the caliphates, while belisarius with less soldiers less resources, internal and external sabotage, remained loyal and steadfast achieving what was nearly impossible, due to his tactics had he not paved the way narses wouldn't have taken even north Africa if he was in his shooes

You're romanticizing loyalty into military genius. Fanaticism is a resource—arguably Khalid's greatest advantage. You claim he later had unlimited resources, then dismiss that by saying Belisarius had worse constraints. Pick one. Either resources matter or they don't. If constraints define greatness, Khalid's early campaigns against Byzantine and Persian empires with ragtag forces are more impressive than Belisarius fighting after Rome spent a century rebuilding. You're also assuming Narses needed Belisarius's groundwork—he might've executed faster without the mess. Belisarius was brilliant tactically, but you're crediting him for obstacles that actually undermine your claim he was supreme. What evidence proves Narses couldn't have succeeded independently?

The topic is the best general, and total impact of course goes for Khalid, however Khalid was not alone from the start of Islam he was supported by hundreds of elite generals, belisarius literally upturned the balance of the world with the sword pushing without any meaningful support

You're shifting criteria mid-argument. First it was constraints, now it's "total impact." Belisarius didn't upend the world—he restored a shrinking empire temporarily. Khalid reshaped three continents permanently. Islam became a superpower partly because of him; the Byzantine Empire never recovered from Belisarius's victories. Scale matters. You dismiss Khalid's generals as "support" while crediting Belisarius's subordinates as proof of his genius. That's backward logic. If Belisarius needed capable officers to execute plans, so did Khalid. The difference: Khalid's impact outlasted empires. Belisarius's conquests crumbled within decades. Which legacy actually changed history?