The church I attend holds its services in an elementary school auditorium. Periodically they will have student work displayed. I must admit that this Sunday I was quite distracted from the sermon. What the assignment was, I cannot tell you. I can only tell you this. Voldemort would win.
Squanto is short for Tisquantum. He was the native american who taught the pilgrims to plant corn. I know this because I did a student teaching lesson on it, back when I still had a passion for teaching. This seems an unfair match up to me. At least peg him against John Smith who had a musket. All Squanto had was a corn cob. Corn cob vs. Elder wand. I'm going to go with Elder wand. A helpful indian vs. the most powerful dark wizard of all time... once again, I'm going with Riddle. I'll give Squanto this. He has a pretty B.A. "q" in his name while VoLdemort only has a misplaced capital "L".