If one was to go with the latter, and chose to see Alexander in a more cynical way then one is sure to think that he does not deserve the title of being "THE GREAT". Just to add to that, it is told that he once murdered his best friend due to a difference in opinions. This says a lot about his character. He is quick to anger, judgmental, and stubborn. Even though he was being stopped by his guards and other friends, Alexander had the "perseverance" to grab a spear and impale his best friend. At least he was devastated when he came to his senses. I guess it would be a good point to include that he was so overly wasted. But that was common for the Macedonians- they drank all the time. and they even won wars drunk. If he is capable of fighting and strategically winning a battle drunk, then why was he not capable to think clearly about killing his best friend? In the cynical viewpoint, was he saddened by the thought that his best friend had died and that he was the hand that dealt the blow or was he worried about his reputation. History shows that a small little place decided to go against his orders one day. Just a little place of no strategic importance filled with mostly women and children. Alexander ordered all these towns to surrender unconditionally to him, they all did but one. So instead of just letting them be, he altered the making of the earth so that he could reach them and destroy them. He sold the women and children into slavery. This could show his devotion to battle or it could show his inhumane side a little bit. The town was of no importance and would not be a great, big addition to his mighty kingdom yet he went out of his way to show to the other little places who were thinking of rebelling that he would do anything, and clearly he meant anything, to show his power and crush them. Ooh, another fun "Alexander when he's drunk story". After conquering the great and mighty Persian empire, Alexander decided to "party it up" at Persepolis. I imagine that his invites would have looked something like this: Party at Persepolis. Be there or be square. Come see me, Alexander the Great and celebrate my victory (yes, another one. I'm just that great). They're just chilling and drinking (what else is new?) and a fair maiden in distress (cliche) decides to speak up about how the Persians should be punched in the face for disrespecting the Greeks and Macedonians a few ole' decades ago. Fired up from his victory and the booze, Alexander picks his drunkard self off the ground and takes the party a notch up and starts to burn the palace down. I'm sure he regretted burning down the palace of the Persian Empire he so admired when he healed from his major hangover. Sure, he was motivated to do this by a girl, he's a guy. He, with all his moral codes and ethics, burned a palace down. A sure sign of disrespect. Ironic, since he chased his enemy's killer down but then proceeds to burn his enemy's kingdom down to the ground. Surely, if he did this in the modern world, he would be accused of being a pyromaniac and the fire department would put him on their blacklist.
Taking on more of a cynical viewpoint, Alexander didn't deserve his title. There's no doubt that he was a good leader in the military aspect. But looking at the big picture, he missed a few points here and there. Looking at this question "does he deserve his title?" in a way you would look at a competition such as a pageant then... I guess we can call this the Mr. Great pageant and to win, you need to have a perfect score. I am confident that he would have scored very highly for his strategic planning and military conquests but he would lose a few points for his personality. To be Mr. Great, you still need to have a great personality even if you're a great military leader. So in this sense, Alexander would score around a 7/10. He doesn't deserve to be called "THE GREAT". Maybe he should have changed his name to something along the lines of "Alexander the A Little Above Average but Still Lacking in the Personality Department."