Headscratchers / Brewster's Millions (1985)

• Why didn't Monty just spend the entire $30 million on rare stamps and mail a bunch of letters?
  • He probably just didn't think of it. And he probably would've been banned from buying rare stamps after the first few, like he was from gambling when all his longshots came through.
  • Who would issue the ban and on which grounds? The crooked lawyers couldn't find anything in the law to close the loophole and whoever sold the rare stamp, unlike the gambling houses, wouldn't lose anything by allowing Monty to buy more.
  • Rare stamps are called that for a reason; they're rare. You can't buy them if there's none actually on the market to be sold.
  • What would prevent Monty from hiring someone to buy on his behalf without the sellers knowing he's the real buyer?
  • He could do that, but in doing so he's gaining an employee — i.e., another asset. And that employee is likely to create more headaches for him as his other friends and employees did by advising him on ways to save his money (i.e. said hypothetical employee is likely to look for good deals for the boss rather than just extravagantly buying the most expensive things possible). And as mentioned above, he can't just buy a whole bunch of rare stamps if there are no rare stamps on the market to be bought. Rare stamps aren't always in constant circulation, they're part of people's collections.
  • Monty has a bit of an issue with trying the same thing more then once...and he DOES do a similar trick. The wine party is a repeat of it. But, since E-bay isn't a thing? He can't just KEEP looking...and if he's not careful, he risks getting an asset...
  • Also, looking at the value? The Inverted Jenny was 1.25 million. (This is a real stamp. The only others that can be found? Are worth $3,000 to $20,000. All others have numbers of less then 100)
• Was there a clause saying if he had any assets at the end of 30 days they would be seized? Once he got near 40 million and found he was having trouble spending, he may as well have just given up on the 300 million.
  • It's implied near the end of Horne's video with line "you don't get diddly!" but I don't think it was ever stated as such.
• Why couldn't Monty have just hired some people at an exorbitant salary? Sure, people might wonder why you're giving your chauffeur a million a day, but they couldn't really stop you.
  • He does do this; he hires at least one person as a photographer and pays him some ridiculous amount of money for it. IIRC though in the movie at least the rules clearly state that he has to get roughly equal, or at least reasonable, value for what he's paying (which, in this case, would probably be linked to the general market value of said service — and how many people pay their chauffeurs a million dollars a day?), so he can't just hire one person for a million dollars a day and fritter it away unless he's getting a service that the market would value as being worth roughly a million dollars per day.
    • So, why couldn't he just hire famous people to do stuff? Surely the market value of, say, Annie Leibovitz being hired as a photographer would be SIGNIFICANLY more than the local studio who take yearbook photos. Get Mario Andretti to chauffeur you in a rented Lamborghini, have Hulk Hogan as a bodyguard, stuff like that. Surely that would be a legal way to spend the extra dough on hiring people.
    • The Doylist answer, of course, is that either the director didn't think of it or those people weren't available. In universe, that still runs into the issue of how valuable the market deems those jobs to be. Sure, you can hire Hulk Hogan to be your bodyguard, but while Hulk would presumably demand a somewhat bigger salary than Larry the bodyguard, the market as a whole still wouldn't value the job of bodyguard as one that merits a salary in the millions (or at least a substantial enough figure for Monty to easily blow through his cash that way). So if Monty hired Hulk at $10 million a day to be his bodyguard, the lawyers would probably object on the grounds that no bodyguard is valued that much, meaning that it would probably be ruled invalid. Similarly, you can hire Mario Andretti to be your chauffeur, but you're still going to be paying him at a chauffeur's rate rather than a race-car driver's rate, because you're hiring him as a chauffeur not a race-car driver. So while hiring a celebrity rather than a regular joe would make a slightly bigger dent in the $30 million, it's still probably not going to be a huge dent.
    • And of course, a celebrity might consider it underneath their dignity or current position to basically act as some millionaire's servant, no matter how much they were offered. Mario Andretti got paid a generous wage specifically to race highly specialised vehicles around complex racing tracks in competition against other more-or-less equally skilled drivers. There's a challenge there that you're probably not going to get ferrying around some rich asshole. You can't spend millions hiring a famous guy to do menial tasks for you if the famous guy tells you to go screw yourself because he considers it an insult.
    • And they might also just be busy. Hulk Hogan and Mario Andretti and Annie Leibovitz presumably weren't just sitting by the phone waiting for a rich guy to offer them work, their services were in demand, they had other things to do as well. Hulk Hogan had wrestling bouts scheduled, Mario Andretti had races to run, Annie Leibovitz probably had a full calendar of photo shoots, and so on. As with the rare stamps above, you can't hire someone's services if their services aren't currently on the market to be hired.
    • It ultimately is covered in the film. One of the conditions is that he must receive value for their services. Paying an extortionist amount for a service that is mundane means he's not receiving the value intrinsic for the position, thus counting as giving the money away.
• Why didn't Monty just buy a bunch of food and drinks for people?
  • The answer is, he does spend a significant amount of money on food and drink. One of the first things he does, in fact, is take a whole group of bystanders, gawkers and hangers-on to lunch—his treat—and buys them all expensive wine to drink. Another thing that gets mentioned in the film is how he buys a number of bottles at an auction of the most expensive old wine he can find, and opens all the bottles at a party afterward. But even doing things like these every day for thirty days wouldn't drain the entire $30 million.
  • Aside from whatever he spent on parties, buying foods and drinks for other people could be considered charity. There's a clause stating no more than 5% of those millions could be donated to charity.
  • It still might be a legal grey area rather than being explicitly defined as charity if those people don't actually need the food and drink he's offering and are just taking advantage of his generosity, but as previously stated, he still spent a considerable amount of money on food and drink and didn't make that much of an impact on the total.
  • As with several of these, the simple answer is that even the highest of high cuisine dining is simply not as expensive as people who can't afford to partake in it regularly assume it is. For example, The Four Seasons was probably one of the fanciest, most exclusive and most expensive restaurants in New York in the 1980s. While exact figures for how much it cost to eat there in 1985 don't seem to be readily available, according to this in 2017 it would cost you about $150 per person for a three course meal there — and the article says this is actually cheaper than it used to be, so let's round it up to $200 in 1985 money per person just for sake of argument (and we'll ignore inflation for purposes of discussion, so a round $200). Assuming Monty treats 20 people to a $200 meal there a night, it's going to set him back $4000 per night — so if he does it every night, that's only $120000 he's spent over a month. Assuming he treats 20 people to breakfast, lunch and dinner there everyday, and each meal costs the same, that only brings it up to $360000. Now, obviously for most average people that's a hugely extravagant sum to spend on eating out over the course of a month — but it's barely a drop in the $30 million that Monty has to work his way through. Now, let's go all out and say that Monty manages to buy out the entire restaurant every breakfast, lunch and dinner for a month and pay the same for every meal for every single person who can fit in it. The Four Seasons could fit about 485 diners. So, three meals a day for 485 people over 30 days is $8730000. Which, granted, is a much larger chunk out of the $300 mil, but (a) practically he's never going to manage to find 485 people to feed for every meal every day, nor will the restaurant — which has numerous other wealthy and powerful customers it doesn't want to offend — be willing to let him book every table every time they're open; (b) buying 485 people's meals every day for a month would start to look like charity, as discussed above; and (c) even setting aside the other considerations, that still leaves him with about $291 million to get through.

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