My boss started a fantasy football league this year with a $20 buy-in with winner-take-all. I don't particularly care for football, but I signed up thinking it would be a good way to socialize with coworkers.

There were a total of 16 teams in our league. It wasn't until after our draft that we realized that 9 of these teams belonged to my boss. Essentially, he had signed up 9 times for the league, drafted a whole bunch of really good players, and then traded them all to one "super team". The app we use predicts that he has a 96% chance of winning.

Somebody confronted my boss about this, and he said it was just strategy. He was asked if he's paying $20 for each team, and he just said don't worry about it. I'm no expert (I've only played once before), but this certainly seems like cheating to me.

I'm not particularly concerned about the money (I can live with losing $20), but I'm a bit annoyed. What's the best way to deal with this situation? All money exchange and drafting took place outside of work, so I'm guessing HR won't want to deal with this. Even if they did, it seems like it could be career suicide for me to report my boss to HR over something like this. I can't quit because this is my dream job. Is it best to just swallow my pride and accept that my boss cheated me out of $20? Or is there a better way to approach this professionally?

  • 12
    Do you have incontrovertible proof that your boss cheated? If a carnival hustler took you for $20.00 on a rigged ring toss game what would you do? Do the same thing in this situation.
    – joeqwerty
    Sep 5, 2019 at 2:53
  • 1
    Yeah, he said he did it. That's my proof. Sep 5, 2019 at 3:23
  • Second attempt at this comment. You hearing him say it is not proof. It is your word against his. Sep 5, 2019 at 10:29
  • 14
    How far along is the season? If it's at the beginning, can you get together with the other legit players and form a super team of your own? I realise it's only 7 teams of players vs 9 teams, but if you can win you stand to get $45 each.
    – Smock
    Sep 5, 2019 at 14:02
  • "I mean, cheating in a fake fight. That's low!" - Leela Sep 9, 2019 at 14:10

7 Answers 7


HR wouldn't be inappropriate to go to, but it wouldn't be advisable on a personal level. This is your dream job. Don't rock the boat.

On principle, I think you should just go to the boss and ask for your money back. If he refuses, just calmly walk away. You gave him the chance to make things right. He didn't take it. Don't accuse him of cheating, just say that you no longer want to be involved.

Him being seen as untrustworthy is going to be punishment enough as it is, once word gets around.

What your boss did is incredibly stupid, as it undermines trust across the team and expels any goodwill that may exist.

What it may do is make your boss a bit of a laughing stock, and drive the rest of you together. Just ignore top place, and make it a race for second.

  • 9
    If I just accept that I lost $20, should I share some of this info with others who may have been scammed by him? Sep 5, 2019 at 2:10
  • 13
    If you do, I would do so in a bemused tone and casually. Don't go charging around the office trying to get people agitated (or be seen to be attempting to do so). Sep 5, 2019 at 2:14
  • 48
    This is the best option. Honestly, the boss was an idiot for even getting in the game. You don't start a competition for money with subordinates. You're supposed to nod knowingly while they pretend they're not playing fantasy football on the clock. Sep 5, 2019 at 4:01
  • 2
    @WesleyLong The other option is to (as the boss) supply a small prize like a bottle of wine and make it a social event.
    – Borgh
    Sep 5, 2019 at 7:39
  • 1
    If an employee behaves in such a manner outside of work that would cause conflict within work, then yes, that is something that HR may like to know about. HR may or may not be able to take disciplinary action, but at the very least they can have a chat with the employee about how their behaviour may impact working relationships. Sep 5, 2019 at 23:35

I agree with the other posts, that this should be done in private. You should also make sure all of other players are on board with you. Check and see if they are upset about this as you are.

If you still can't get your money back from your manager, then I suggest you use strategy as well. You said it was a 16 team league. I suggest coordinating with the other 7 teams and creating a second super team. You should have plenty of good players to compete against him. Plus you will have the advantage of having 7 people searching the waiver wires and helping strategize your lineup each week. You could actually turn this into a bit of team building! I am sure his 96% winning chance would drop to mid 55% at best with HIS OWN STRATEGY!

At the end of the season, if you lose, you lost your money anyway. If you win, your boss now has to cough up $180 that you can now split with your superteam cohorts. On top of that, you now have a stronger relationship with your coworkers.

May not be the most "professional" response, but it sure would be a lot of fun. I am smiling to myself just thinking about what his face would look like if you win the championship and has to pay you all for using his strategy.

  • 2
    I was going to suggest this, but it probably wouldn't be much fun for the people actually interested in the football aspect of the game. The game is already tainted for people playing socially or just for fun, but I'd expect at least a few people get enjoyment out of managing their team and watching their standing rise or fall each week. If everyone pools their players, the individual pleasure of management and competition is lost. I agree this is a great way to "get back" at the boss, but I think it might only make the game less fun in the end. Sep 5, 2019 at 12:49
  • 3
    That is actually the exact answer that I wanted to write. Do the same to him and see this as the team coming together to solve a problem.
    – Tom
    Sep 5, 2019 at 12:49
  • 1
    @NuclearWang yes but now the enjoyment comes from the smug satisfaction of doing in the guy who tried to do you all in.
    – Stun Brick
    Sep 5, 2019 at 13:34
  • 3
    This whole scheme isn't going to make your boss any less of an asshole. Take your lumps and turn the page. You paid a low tuition to learn an important life lesson.
    – Tim Nevins
    Sep 5, 2019 at 13:50
  • 1
    Yeah I added this as a comment before seeing this - If the 7 club together and manage to beat him they can win $45 each
    – Smock
    Sep 5, 2019 at 14:04

You didn't say who confronted the boss, but the most experienced and most trusted person in the department needs to confront him a bit more ... forcefully ... and explain that what he has done will eventually destroy trust.

The manager should be asked, in private, to return all of the money and apologize. It should be made completely clear that the manager can follow that advice, or the rest of the players will stop playing. They have little or no chance of winning, so they might as well cut their losses and save the time.

And yes, managers should refrain from competing against employees.

  • 1
    I think it depends on the nature of the power dynamic. My team went go-carting a few months ago, including my supervisor and my manager, and we all had a good time. I think it's a bit more dicey when money is involved. Especially non-trivial amounts. Sep 5, 2019 at 4:16
  • 2
    That last lien is the face-saver. The official reason to cancel need not be the cheating.
    – MSalters
    Sep 5, 2019 at 12:16
  • @GregoryCurrie - When I worked for a Very Large Company, all competition involving managers was all-manager teams against all-rank-and-file teams. There were a number of advantages, not the least of which was we were all young and healthy, and the managers were all old people :) In my early 30s I was quite adept at beach volleyball and many a manager felt my wrath on the other side of a wicked serve. Life was very good. Sep 5, 2019 at 13:14

This is too small an issue to start making official complaints about, and as you say it is not technically cheating. Serous retribution is only going to make matters worse for yourselves. And as Bobby Tables says, paying $20 to find out your boss is an asshole is a pretty cheap lesson.

However think about why your boss might be doing this. It's not about the money, it's about showing himself to be the smartest guy on the block. It's a pretty childish way of doing it, but it's probably what he wants.

Your response to thwart this is simply to get everyone to stop paying attention to the league. If you can get the other players on board, simply stop publishing updates; stop making trades; stop looking at the results; stop talking about the results. Believe me, it's no fun winning a competition that nobody is interested in. Pay him the money when he wins - in fact consider giving it to him early since "it's obvious that he's going to win". If he starts talking about the league just say you've stopped paying attention to it since it's not interesting any more.

And next year, if you do it, think about what rules you want in place to prevent this happening again.

  • Yes, the best thing is consider the $20 bucks lost and just let this league die. It may be too late for league fantasy, but I would've gotten the other 7 guys (excluding the boss) and started a new league (or a survival/standard pool).
    – pboss3010
    Sep 5, 2019 at 19:17

Whatever you say or do, do not count on making your boss "see the light" (as in, really understand what did he do wrong, and repent).

Think about this: even from a purely selfish viewpoint, in a game of 16 teams, 9 of which are his, all he stands to gain is 7x$20 = $140. That's a negligible amount, especially on a manager-level salary.

What he's going to lose is the trust of all seven people AND of everyone else who hears about it. Then people will not trust him in much more important matters.

What I'm trying to say is, it's stupid - even if you don't consider ethics at all, it's stupid. It's throwing away something that's much more important, and that takes a long time to earn, for a chump-change amount of money.

(No, I do not say that it would be OK if he did it for a million dollars; just that it's not merely unethical but dumb.)

The practical consequences for you - you need to assume that this is a problem of a type that even at best won't be fixed in less than many years or even decades; and possibly not in his whole life. And chances are that you aren't going to be the one to fix it.

That being so, you can:

  • avoid him, quit this fantasy football and the whole idea of any activity where he is involved
  • return it in the same way - as other people here described, join with other players and use the same tactics
  • eventually find another job as good as this one. It might take some time, if this is your dream job, but if such lack of ethics spills over on the job itself, sooner or later you will have to.

I agree with most answers here. Do not make too much fuss over this (and do not join again). I like the teaming up against him with the other players, but I guess it depends on your boss whether he will appreciate being beaten at his own game.

If there is any form of proof I would inform the other players.

What I would like to add is that in my opinion this is really not something for HR. 1) As you mentioned it took place outside of work and 2) depending on your country this could (as it would be in mine) officially be considered as gambling and therefore illegal. That would be another reason HR is very likely reluctant to get involved.


Many companies have rules regarding contests or gambling. Fantasy football with a money buy in might be a violation of rules at your company. Some companies have relaxed rules about this such as doing a limitation cap on how much you can contribute (usually $5 at the most). My guess is that you're all in violation of company policies. Most companies will mandate that you can play fantasy football so long as the prize isn't monetary.

However, this falls under buyer beware. Yes, it's rotten your boss gamed the system by using multiple teams to hold all the good players. Unrelated, I played fantasy football before and had a very low chance of winning but in the end, I somehow managed to win. I found the QBs where you want to get a good collection of as the other players tend to injure out. Back on topic, yes, it's rotten your boss did this, and it may very well be a strategy sort of like back in 1998 when we played N64 with a group of friends and one of them is looking at your screen to cheat. It's cheap, but there's always that one person who does it and it always happen to be the kid that owned the system. Just take it as a lesson and move on.

  • I never understood why the other kids weren‘t looking at the other screens...infact I always assumed they were? It was an equal advantage for everyone... Sep 25, 2019 at 16:48

You must log in to answer this question.

Not the answer you're looking for? Browse other questions tagged .