Stories That Stick continues with the start of our True Stories theme, and this week Cade brings Moneyball — the real-life story of Billy Beane and the Oakland A’s as they attempt to rebuild a failing team using analytics instead of tradition. Cade chose this film because it perfectly reflects his own love for logic, metrics, and decision-making rooted in data rather than emotion. The movie follows Billy, a former player who regrets choosing baseball over a full-ride education, as he fights to build a competitive roster with almost no budget after losing his three star athletes.

The heart of the discussion centers around Billy’s unexpected partnership with Peter Brand, a young economics grad whose statistical model focuses on one thing: how often players get on base. Scouts rely on instincts, vibes, attractiveness, and outdated criteria, while Peter brings a system that exposes how wrong those instincts can be. Cade and Kit talk through how the film captures the conflict between old-school baseball thinking and innovation, and how Billy faces enormous resistance from scouts, management, and especially the coach, who refuses to play the players chosen through analytics.

The team struggles at first because the coach actively sabotages Billy’s vision, sticking to his own favourites and ignoring the data. Billy ultimately forces alignment by trading away the players the coach insists on using, leaving him no choice but to play the analytics lineup. This shift leads to the incredible 20-game winning streak that becomes the centerpiece of the film — a streak that proves the model works even if the league hates admitting it. Cade and Kit unpack how leadership, pressure, and conviction all show up in Billy’s choices, and why going against the grain demands both grit and risk tolerance.

A major part of the conversation explores the Red Sox offering Billy a record-breaking $12.5M contract to bring the Moneyball model to Boston. Kit argues she would’ve taken the job for the resources and scalability, while Cade highlights the emotional reasons Billy declined: his daughter, his regret about chasing money earlier in life, and his desire to win with the A’s on his own terms. The irony, of course, is that Boston wins the World Series the next year using his model.

Cade and Kit also touch on the acting, noting that the story itself is stronger than the performances. Cade didn’t find Brad Pitt’s portrayal particularly memorable, while Kit loved Jonah Hill’s quieter role and the film’s overall pacing. Together, they agree it’s a great story with lighter execution — more of a “smart movie” than an emotional one.

Kit rates Moneyball a 7.5 for its innovation and message, while Cade gives it a 6.5 for being a strong story but not something he’d rewatch for the performances. It’s an episode about data, leadership, and challenging the norms — and a great start to the true-story arc in Season Three.

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