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In this episode of Trackin' Tracker, the gang dives into Colter's first case in a major city: Chicago. The hosts debate if Bobby will ever escape the friend zone with Sun Mai, Colter's potential political leanings, and whether he's an adventure seeker, some well-off wealthy do-gooder, or just bad at business economics. Ryan, Mike, and Scott also wonder how did Colter train to become an amazing fighter and magician.

00:16 Episode Summary: Chicago
01:50 Discussion: Episode Impressions
03:02 Character Analysis: Bobby's Role
05:20 Speculations: Colter's Political Views
10:28 Character Analysis: Rennie's Legal Expertise
17:32 Financial Breakdown: Colter's Business Model
24:51 Living Expenses and Financial Struggles
27:41 Colter's Risky Lifestyle and Financial Model
34:06 Unanswered Questions and Theories
39:04 Character Dynamics and Future Predictions
41:44 Episode Review and Final Thoughts

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In this episode of Trackin' Tracker, Colter enters the high-stakes world of horse racing and works with a former flame. Ryan, Mike, and Scott discuss how much money it would take to scam high powered clients by selling a dud of a horse, if Colter cares about being a law abiding citizen, and Billie's power over Colter because the potential of sex. The gang also reveal their dream team line ups for their own tracking team.

00:39 Plot Breakdown: Lexington's Big Prize
01:05 Character Dynamics and Relationships
02:17 Episode Highlights and Theories
04:05 Deep Dive: Legal and Ethical Questions
07:04 Speculations on Character Backgrounds
09:30 Romantic Tensions and Future Predictions
20:48 Imagining the Ideal Support Team
21:30 Scott's Dream Team Breakdown
26:12 Ryan's Strategic Team Choices
29:23 Mike's Comprehensive Team Strategy
32:44 Concluding Thoughts and Next Episode Preview

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In this precursor pilot episode of the global podcast Trackin Tracker, Mike, Scott, and Ryan discuss Episode 5 - St. Louis. The gang question how Colter has the cash to get into the secret backroom poker game, what type of legal and travel fees Reenie charges Colter, and what kind of mental state Colter will be in after a surprisingly dark ending.