Story Structure — 4 Plot Phases
The Leap of Faith
The protagonist abandons a stable corporate career to pursue an obsessive dream. He secures unprecedented access to the Chicago Cubs organization.
Key Events
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Quitting the Day Job — Protagonist leaves corporate employment to pursue an obsessive dream. Location: Home Office
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Securing Team Access — Gains unprecedented behind-the-scenes access to the franchise. Location: Wrigley Field
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Rallying the City — Organizes massive fan mobilization to show unwavering support. Location: Chicago Streets
The Crusade Begins
Massive fan mobilization sweeps across Chicago as the protagonist rallies the city. He steps into front office negotiations to facilitate a crucial trade.
Key Events
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Rallying the City — Organizes massive fan mobilization to show unwavering support. Location: Chicago Streets
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Facilitating a Trade — Steps in to help negotiate a player exchange for the team. Location: Front Office
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The $20 Million Loan — Attempts to secure massive funding for team payroll operations. Location: Bank
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Bank Rejection — Financial institutions refuse the unconventional funding request. Location: Bank Office
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Trade Negotiation Success — Player exchange officially completed. Location: Front Office
The Financial Hurdle
Institutional funding is denied, forcing a pivot to grassroots crowdfunding. The team enters a critical late-season stretch with city-wide support.
Key Events
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Bank Rejection — Financial institutions refuse the unconventional funding request. Location: Bank Office
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Fan Fundraising Drive — Turns to grassroots crowdfunding after institutional failure. Location: Community Center
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Media Sensation — Gains national attention for extreme fandom antics. Location: TV Studio
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Locker Room Visit — Interacts directly with players and coaching staff. Location: Cubs Dugout
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Playoff Push Begins — Team enters critical late-season stretch for postseason berth. Location: Wrigley Field
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City United in Hope — Entire population rallies behind the team's championship chances. Location: Chicago Neighborhoods
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Loan Alternative Found — Grassroots support replaces institutional funding. Location: Community Hall
Victory and Reflection
A high-stakes game secures the playoff berth, triggering city-wide celebrations. The documentary concludes with reflections on the legacy of extreme fandom.
Key Events
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City United in Hope — Entire population rallies behind the team's championship chances. Location: Chicago Neighborhoods
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The Crucial Game — High-stakes match determines postseason fate. Location: Wrigley Field
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Victory Celebration — Team secures playoff berth, city erupts in joy. Location: Chicago Streets
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World Series Dream Alive — Official announcement confirms postseason qualification. Location: Press Conference
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Fan's Ultimate Reward — Protagonist experiences the culmination of his crusade. Location: Stadium
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Documentary Filming — Behind-the-scenes capture of the journey's conclusion. Location: Various Locations
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Legacy of Fandom — Reflection on the impact of extreme dedication. Location: Chicago
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Credits Roll — Final acknowledgments and closing thoughts. Location: Theater
"Chasing October" is a docu-comedy that chronicles one fan's crusade to take the Chicago Cubs to the World Series "by any means necessary." Director Matt Liston quits his job, gets all access to his favorite team, and rallies a city. Perhaps no other fan in the history of sports has gone to such an extreme. See Liston as he helps facilitate a trade, attempts to get a $20 million loan to help team payroll, and takes being a fan to a whole new level. This film is a hilarious must-see for all sports fans and for anyone who has ever chased a dream.