So You’re In A Fantasy Football League With Your Boss

So You're In A Fantasy Football League With Your Boss

I’ve been bitter since the end of my run in the Grandex fantasy football league last season. I’m not a seasoned vet to fantasy football, but I’m a numbers guy. It was my major, and it’s my current profession. I have more spreadsheets on NFL players than I have work-related spreadsheets. But my fatal mistake was looking into speculation- I was being too cute, if you will. I read into the rumor that Eddie Lacy would be rested at the end of the regular season since he was getting banged up all season long. Thinking I’ll just sit my man, Eddie, and put in James Starks and rack up some points in a very, very limited waiver wire (we had 18 teams in the league). To my dissatisfaction, that Sunday Eddie Lacy was the man behind every run play while Starks was viewing the game from the bench. I blew it all away and JayTas advanced to the next round of playoffs. I lost to JayTas. I’ll never forgive myself.

Fast forward to today, and fantasy football is about to start up again. Commissioners everywhere are getting head counts, you have downloaded draft board and projection spreadsheets from Google and you’re binge listening to ESPN fantasy podcasts. You know it’s going to be your year.

There’s a good chance you are going to get in on a fantasy league full of coworkers. Sometimes this may include your boss or someone higher up the food chain than you. This can be pretty dicey. I mean, it only takes one overly competitive manager who is in charge of your salary to decide you’re not getting that generous holiday bonus this year. Here are some strategies you can take to get on your superiors’ good side.

The Standard Handicap

The pretty standard approach is to let your manager, boss, or supervisor win when you play them. This is also the least harmful game plan for your own record. Losing one game is most likely not going to determine whether you make the playoffs or not. Just give them the game. You can always fight another day.

Buddy Buddy

If you are okay with having a shitty team all season, you could always just propose strongly one-sided trades to your boss. Peyton Manning for Frank Gore and Tim Tebow? You bet your ass you are making that trade. On the other side, your superior might notice your attempt and figuratively kill you off like a beloved character on Game of Thrones. Ass kissing is not appreciated by most in the office nor in fantasy football.

Starter Spotting

Just like the guy who is lifting way too much weight at the gym, you sometimes need to give them a little support when they struggle and ultimately embarrass themselves. Your boss might be in fantasy limbo between starting the Jaguars D/ST or the Dolphins D/ST. You need to get in there and give him the best fighting chance. If he wins, you will look like a star- someone they can really look towards when they need someone to lean on in the future. Maybe they’ll think your fantasy knowledge and work ethic somehow equates to your job and promote you. You will be moving up the company ladder faster than any backup QB behind Carson Palmer or RGIII, my friends.


If all else fails and you have a few rolls of cash, you could just pay people off. Throw Daniel in HR a $50 to start an incomplete lineup so your supervisor wins the week. Buy Dunkin for a week for Liz in Accounting. Whatever their price is, pay it. The goal is your year end bonus being double whatever you are paying out this season. Everyone is happy in the end.

The Blend

Like an NFL playbook or an investment portfolio, diversity is key. This applies to your fantasy league. Maybe go easy on them when you go head to head. Follow that up with a one-sided trade the next week. Give them that support when they’re trying to pick the best Flex. Pay off some greedy coworkers. And when it’s all said and done, you can walk into your manager’s office the next day and claim their success was due to your advice. “What did I tell you! I told you to start AP!”

Lights Out

Maybe a change of thought, but your boss might just be the kind of person who is impressed with the effort of a go-getter, or maybe you just hate your boss and this is the best way to throw down the hammer. Either way, if you’re going to stick to your imaginary guns, let ‘em have it and don’t go easy. And remember, if you don’t repeatedly rub their face in the excrement that is their team’s performance against yours, you didn’t technically win.

Whichever strategy you choose, good luck out there.

Image via Shutterstock

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