Theodore Roosevelt & Trust-Busting

Active learning works well for this topic because it helps students move beyond textbook descriptions of Roosevelt’s policies to grapple with real-world trade-offs. Debates and gallery walks create space for students to weigh competing values, while role-based analysis makes abstract ideas like ‘good trusts’ and ‘bad trusts’ tangible and memorable.

• 11th Grade
• US History
• 4 activities
• 20 min–50 min

Learning Objectives

1. Analyze Theodore Roosevelt's 'Square Deal' by identifying its three main components and explaining their intended impact on American society.
2. Explain the legal and economic arguments used by Theodore Roosevelt to classify trusts as 'good' or 'bad'.
3. Evaluate the effectiveness of the Sherman Antitrust Act during Roosevelt's presidency by comparing the number of suits filed and the outcomes.
4. Synthesize primary source documents to articulate arguments for and against government regulation of big business during the Progressive Era.
5. Critique Theodore Roosevelt's conservation policies by examining the balance between resource development and preservation in specific national parks or forests.

Formal Debate

⏱ 50 min·Small Groups

Formal Debate: Should Government Break Up Big Business?

Students are assigned positions as captains of industry (representing trusts), consumer advocates, and Progressive reformers. Each group prepares a three-minute argument using evidence from provided documents about monopoly pricing, labor conditions, and corporate profits. After the debate, students vote on the most persuasive argument and explain their reasoning.

Prepare & details

Analyze Theodore Roosevelt's 'Square Deal' and his approach to regulating big business.

Facilitation Tip: During the debate, assign roles (corporate lawyer, consumer advocate, labor leader) so students prepare arguments grounded in specific historical details.

Setup: Two teams facing each other, audience seating for the rest

Materials: Debate proposition card, Research brief for each side, Judging rubric for audience, Timer

• Analyze
• Evaluate
• Create
• Self-Management
• Decision-Making

Gallery Walk

⏱ 40 min·Pairs

Gallery Walk: TR's Square Deal in Action

Post six stations featuring primary source documents and political cartoons about specific trust-busting cases, consumer protection laws (Pure Food and Drug Act), and conservation decisions. Students rotate with a recording sheet, noting the problem TR was responding to and the government action taken. Debrief builds a complete picture of what the Square Deal actually accomplished.

Prepare & details

Explain the concept of 'trust-busting' and its impact on corporate power.

Facilitation Tip: Before the gallery walk, model how to annotate a political cartoon or photograph with questions that reveal bias or perspective.

Setup: Wall space or tables arranged around room perimeter

Materials: Large paper/poster boards, Markers, Sticky notes for feedback

• Understand
• Apply
• Analyze
• Create
• Relationship Skills
• Social Awareness

Think-Pair-Share

⏱ 20 min·Pairs

Think-Pair-Share: Was TR a True Progressive?

Students read two short excerpts: one from a Progressive reformer praising TR and one from a labor organizer criticizing his limits. Partners discuss whether the Square Deal went far enough, then share with the class. The teacher records positions on a spectrum chart to make the range of views visible.

Prepare & details

Evaluate Roosevelt's legacy in environmental conservation and the creation of national parks.

Facilitation Tip: Use a visible timer during the think-pair-share to ensure equitable airtime and prevent one student from dominating the discussion.

Setup: Standard classroom seating; students turn to a neighbor

Materials: Discussion prompt (projected or printed), Optional: recording sheet for pairs

• Understand
• Apply
• Analyze
• Self-Awareness
• Relationship Skills

Jigsaw

⏱ 45 min·Small Groups

Jigsaw: The Three Pillars of TR's Square Deal

Divide students into three expert groups: trust regulation, consumer protection, and conservation. Each group analyzes a document set and prepares a summary. Students then regroup into mixed teams to teach each other, building a complete picture of the Square Deal's scope and legacy before writing an individual synthesis.

Prepare & details

Analyze Theodore Roosevelt's 'Square Deal' and his approach to regulating big business.

Facilitation Tip: Divide the jigsaw articles by historical significance rather than length so each group contributes equal weight to the final Square Deal summary.

Setup: Flexible seating for regrouping

Materials: Expert group reading packets, Note-taking template, Summary graphic organizer

• Understand
• Analyze
• Evaluate
• Relationship Skills
• Self-Management

Teaching This Topic

Experienced teachers begin by situating Roosevelt’s policies in their historical context: Gilded Age inequality, rapid corporate consolidation, and public outrage. Rather than treating trust-busting as a simple morality tale, they emphasize the legal and political calculations behind each case. Research shows that when students analyze primary sources in real time, they build confidence in interpreting complex texts and develop sharper historical empathy. Avoid the trap of framing Roosevelt as either hero or villain; instead, focus on the constraints he faced and the choices he made.

What to Expect

By the end of these activities, students should be able to explain Roosevelt’s use of the Sherman Antitrust Act, evaluate his distinction between good and bad trusts, and connect conservation to his broader economic nationalism. Evidence should come from primary sources and student-led discussion, not just lecture notes.

Watch Out for These Misconceptions

Common Misconception

During the Debate: Should Government Break Up Big Business?, watch for students who claim Roosevelt wanted to destroy all trusts.

What to Teach Instead

During the debate, have students reread a transcribed excerpt from Roosevelt’s 1902 speech on ‘good’ and ‘bad’ trusts before they argue. Ask them to highlight the sentence that states size alone is not the issue, and call on those who cite it to refute oversimplified claims.

Common Misconception

During the Gallery Walk: TR's Square Deal in Action, watch for students who assume conservation was solely about protecting trees.

What to Teach Instead

During the gallery walk, place a copy of Roosevelt’s 1908 message to Congress next to a map of early national forests. Ask students to annotate how he links conservation to preventing private monopolies over water, timber, and mineral resources.

Assessment Ideas

Discussion Prompt

After the Debate: Should Government Break Up Big Business?, pose the question, ‘Was Theodore Roosevelt primarily a reformer or a protector of big business?’ Have each student contribute one sentence using specific examples from the debate evidence and primary sources.

Exit Ticket

After the Jigsaw: The Three Pillars of TR's Square Deal, on one side of an index card, have students write a one-sentence definition of ‘trust-busting’ in their own words. On the other side, ask them to list one specific trust Roosevelt targeted and the reason it was considered ‘bad’.

Quick Check

During the Think-Pair-Share: Was TR a True Progressive?, present students with a short excerpt from a Roosevelt speech about conservation. Ask them to identify two specific actions he advocated for and explain how these actions align with the principles of the ‘Square Deal’.

Extensions & Scaffolding

• Challenge: Ask early finishers to draft a memo from Roosevelt to his attorney general justifying the Standard Oil case, using evidence from the Northern Securities precedent.
• Scaffolding: Provide sentence stems for the exit ticket and a word bank of key terms (monopoly, public interest, conservation) for students who need language support.
• Deeper: Invite students to research a modern antitrust case and compare the government’s reasoning to Roosevelt’s arguments in the 1902 Northern Securities suit.

Key Vocabulary

Trust-Busting	The practice of breaking up large, monopolistic companies, often called trusts, that were seen as harmful to competition and consumers.
Square Deal	Theodore Roosevelt's domestic program that aimed to protect consumers from business, conserve natural resources, and control corporations.
Sherman Antitrust Act	An 1890 federal law that outlawed monopolistic business practices, intended to prevent the formation of trusts and monopolies.
Conservation	The protection, preservation, management, or restoration of natural environments and the ecological communities that inhabit them.
Progressive Era	A period of widespread social activism and political reform across the United States, roughly from the 1890s to the 1920s.