What to read, watch, and listen to if you lovedLucky Loser
Russ Buettner and Susanne Craig · Book
If you loved Lucky Loser, start with Inside Trump's Head (2026) — a podcast on the same thread. Below: 4 films, 4 series and 2 podcasts, each matched to Lucky Loser across media.
What hooked you in Lucky Loser was the way it pulls back the curtain on how immense wealth weaponizes influence and shapes reality.
Films on the same thread
The Housemaid
Paul Feig · Film · 2025
Shares a thread with Lucky Loser: Power Dynamics.
Much like the investigative spirit of Lucky Loser, this story exposes the dark, manipulative power dynamics that flourish behind the closed doors of the ultra-wealthy and their private lives.
Foxcatcher
Bennett Miller · Film · 2014
Explores: toxic masculinity, obsession, mentor-mentee relationship.
If the dissection of ego and status in Lucky Loser resonated with you, this film offers a chilling look at how unchecked wealth creates dangerous, toxic environments for others.
The Big Short
Adam McKay · Film · 2015
Explores: Economic collapse, Corporate greed, Systemic corruption.
You will appreciate this film for the same reason you read Lucky Loser: it strips away the polish of financial success to reveal the systemic corruption lurking underneath.
Knives Out
Rian Johnson · Film · 2019
Explores: Family Secrets, Wealth and Privilege, Inheritance.
This mystery mirrors the exploration of family legacies found in Lucky Loser, using the backdrop of extreme privilege to examine the secrets that define an influential, wealthy dynasty.
Series on the same thread
The Jinx: The Life and Deaths of Robert Durst
Andrew Jarecki · Series · 2015
Explores: Wealth and Privilege, Elusive Justice, Unsolved Mystery.
If you were fascinated by the sense of untouchable status in Lucky Loser, this true crime series provides a gripping look at how immense personal wealth facilitates absolute impunity.
Billions
Andrew Ross Sorkin · Series · 2016
Shares a thread with Lucky Loser: Power Dynamics.
The high-stakes power plays in this drama echo the cutthroat environment depicted in Lucky Loser, showcasing how the elite use their vast resources to manipulate the world around them.
Winning Time: The Rise of the Lakers Dynasty
Jim Hecht · Series · 2022
Explores: Team Dynamics, Fame and Fortune, 1980s Culture.
This series captures the same intersection of fame and fortune found in Lucky Loser, documenting how a dominant legacy is constructed through ambition, money, and complex team dynamics.
The Loudest Voice
Tom McCarthy · Series · 2019
Shares a thread with Lucky Loser: Power dynamics.
Like Lucky Loser, this biographical drama focuses on the immense influence of a singular figure, highlighting how power is wielded to reshape political and media landscapes for gain.
Podcasts on the same thread
Inside Trump's Head
Podcast · 2026
Shares 3 threads with Lucky Loser: power dynamics, political biography, investigative journalism.
If the psychological profile of the subject in Lucky Loser captivated you, this podcast offers a deeper analysis of the personality traits that drive extreme power and influence.
FiveThirtyEight Politics
Podcast
Explores: polling data, political forecasting, policy analysis.
For those who appreciated the analytical rigor of Lucky Loser, this podcast provides the necessary data-driven context to understand the political mechanisms that sustain the elite today.
Keep exploring
Common questions
Is Lucky Loser written by journalists?
Yes, Lucky Loser was written by Russ Buettner and Susanne Craig. Both authors are Pulitzer Prize-winning reporters for The New York Times who specialize in investigative journalism regarding financial and political matters.
What is the primary focus of Lucky Loser?
Lucky Loser focuses on the financial history of Donald Trump. The book details the specific fortunes and failures that have shaped his wealth throughout his career as reported by the authors.
Does Lucky Loser cover Donald Trump's entire financial history?
Lucky Loser provides a detailed account of the fortunes and failures behind Donald Trump's wealth. The book is authored by New York Times reporters who utilize their investigative expertise to examine these financial events.
Who published Lucky Loser?
Lucky Loser is a book authored by Pulitzer Prize-winning New York Times reporters Russ Buettner and Susanne Craig. The work centers on their investigative findings regarding the financial background and business history of Donald Trump.