I didn’t have high hopes for the book. I’m skeptical about most first-person books in general. People, even the best-intentioned, are hard to trust. I thought this book was likely to be a biased, untrustworthy work, the work of someone with bones to pick, who filters all the events through his later anger. I was pleased to find this wasn’t the case. O’Donnell comes across very fair and very objective in his descriptions.
I strongly recommend the book, as I think it gives great insight into Trump’s character and personality.
Some of the main things that stood out:
Trump is strangely clueless about the casino business: There’s a very illuminating story near the end of the book that describes the author (a high-up Trump casino executive) and his associates trying to lure in a valuable Japanese whale (i.e., high-stakes gambler) named Akio Kashiwagi. This was a guy who played for $200K a hand at baccarat. They were trying to get him in at the Trump properties in Atlantic City. This was the culmination of a lot of outreach the casino executives had been doing in Asia, trying to lure in exactly such high-limit trade.
Trump was very nervous about the guy playing and sweated him playing, worrying about relatively small swings in the game. He wondered whether they should cut the guy off. The author was incredulous at Trump questioning whether they wanted the guy's action. This was a clear win to have the whale play there. Anyone with basic business sense would know that it was a win. Later, after the whale returned to play a few months later, Trump actually cut the whale off from action even though he'd promised him more play.
Another aspect: Trump has very strange business practices. When he owns several casinos in Atlantic City, he pits them against each other, so they are basically driving up business costs in trying to compete and cannibalize each others' customers and prospects. The author describes in detail how dumb a strategy this was. Trump seemed to enjoy pitting people against each other, despite it being clearly a losing strategy that increased costs and inefficiencies. This seemed to be one factor amongst many that led to bankruptcy for all of these biz ventures.
Trump’s abnormal forgetfulness: The book details several instances of Trump’s strange forgetfulness and lack of focus. In several entertaining stories, the author describes several business projects where Trump continually acts clueless about what’s going on, despite the decisions being discussed and agreed upon many times. Most of these stories culminate in an angry outburst from Trump when he finds out how much something is costing him, with his associates completely perplexed because the plans had all been discussed multiple times with him already. It is hard to believe, but completely in keeping with what we've seen of Trump in recent years; forgetful, illogical, near-delusional.
Trump's vindictiveness in deal-making: The book describes several deals where Trump's main goal seemed to be screwing over his "opponent" as much as possible. And he also seemed open about not hiding the fact much that he was screwing these people over. The author describes the lies/exaggerations Trump would tell in his mission to complete a deal. While this might be okay for a 'scorched-earth' business/negotiation tactic, where you are only interested in a single deal or a short-term win, it's clearly not a good strategy when you are in business long-term and want to earn repeat deals and build relationships longterm. At the very least, you'd think if you were going to get one over on someone, you'd want to make that a little more subtle, so there'd be some plausible deniability about whether someone was fooled/conned. But Trump has never been very subtle.
All the anecdotes and stories in the book drive home the point that Trump should in no way have a reputation as a savvy businessman. I was actually shocked at how ludicrous some of these stories were, despite already having a very low opinion of Trump already. I very much recommend this book for getting insight into Trump's mental state and outlook.
I thought I'd share a few reasons why I trust O’Donnell’s memoir and his version of events, and why this book is different from other “hatchet jobs”:
• His descriptions stay dispassionate. In an ideal world, these types of books would avoid passion and be objective. But often first-person accounts are super-biased and the author’s emotions color everything, to where you don’t feel like you can trust anything they say. But O’Donnell stays very calm and objective, backing up his analysis of Trump’s decisions with solid explanations. O’Donnell clearly had many valid reasons to very much dislike Trump, but his reporting stays very fact-based and avoids emotional outbursts.
• He had money. For some books like these, you get the sense that the author is writing it for the money or the attention, and therefore you suspect an incentive to make the book be as sensational as can be. If this book had been written by a distant accountant or chauffeur Trump worked for, it would have been much less-trustworthy. But this book is written by a guy who was making a lot of money, and not long after he stops working for Trump, he’s found another job as a high-up executive at another resort/casino company, presumably making a lot of money again. If anything, O’Donnell was risking his reputation in the casino industry, an industry that hugely values confidentiality, with such a book. He was also risking being sued by Trump, who he knew was litigation-happy and who he knew held grudges for a long time. Both of these factors lend a lot of weight to his tale.
• He seems very honorable. There’s a part at the end where O’Donnell, after resigning his job for Trump in an emotional confrontation, is asked to go to a legal hearing against Trump, and he shows up and tells the truth, which helped Trump. Trump is amazed that O’Donnell would help him; he expected him to lie to hurt him. O’Donnell tells Trump that that’s not the kind of guy he is. And indeed he comes across as very honest and honorable in multiple spots.