This activity has been fantastic for me! Teddy was a larger than life figure and this assignment makes that clear. I compiled 15 large, high-resolution, colorful primary source political cartoons featuring Teddy Roosevelt and focusing on a variety of topics, from Progressive breakthroughs and Labor Strikes to Imperialism and his legendary "Big Stick" Foreign Policy. Some celebrate him, some criticize him, and some are open to interpretation. I included a graphic organizer which guides students through the cartoons and asks them to identify the general topic and explain the specific meaning of each cartoon. I have used this assignment as a culminating activity, a review, a quiz, and an introductory assignment, and staged it as group work, a gallery walk, an on-line activity, and individual homework.
To provide some context prior to this, I suggest using my "Teddy Roosevelt: Big Stick Diplomacy", a quick but thorough means of covering his foreign policy.