How To Win $1,000 Playing Fantasy Football

Do you love fantasy football? Do you love gambling and winning lots of money? Then we have two things in common because like many football loving Americans I love both. This past year I joined my first 32 team dynasty league and by the end of the season I took home the first place trophy of $1,000. Below I’m going to break down how to win $1,000 playing fantasy football and hopefully help you bring home some cash next season while having some fun in the process.


Step 1: Find a 32 Team League

Welcome to a new year of fantasy football. Rarely do people consider February as the start to the new year since we just finished watching the Super Bowl, but this is when dynasty season truly begins. This is also the time new dynasty leagues start forming and existing leagues start looking for new owners.

First off let me explain why I recommend joining a 32 team league instead of the more popular 16 team league. In a league so big there is something happening all the time. You see more trades, the chat and message boards are much more active, and overall in my personal opinion they are a lot more fun. While all of those reasons are great, the most important reason to join a 32 team league is that with a bigger league, you are playing for a bigger pot. One thing I forgot to mention earlier about my $1,000 trophy is that my entry fee was only $50 for this league. Many 32 team leagues are fairly cheap (many are under $50 a year) and have huge payouts (up to $1,000 for the winner). These leagues offer huge rewards with very low risk and that’s why they are the first step towards making $1,000.

In terms of finding a league, the best place to look is on MFL message boards or on twitter. These leagues are everywhere, but sometimes you have to put some work in to find the one right for you. Make sure to carefully read the bylaws and speak to some owners before making your choice, because the goal is to find a league you want to participate in for many years to come.

Click here and go to “Leagues looking for owners, owners looking for leagues” to find the right league for you!

Step 2: Build a Strategy

Once you find the league that is right for you the next step is building a strategy. Many people go into the first auction without a plan in mind and it hurts them right away. They aren’t always fully aware of the salary cap or the point structure which value some positions over others. Below are a couple recommendations on building a sound strategy and having a strong plan before you bid on your first target:

  • Look at the starting lineup requirements and roster maximum to plan how many players you ideally want on your team, first broken offense vs. defense, and then per position.
    • For example: in a league where you only need to start 1 RB but 3 WRs, you want to make sure you plan to have greater depth at WR on your roster
  • Budget out the salary cap the same way you built your ideal roster, first by breaking offense vs. defense, and then deciding how much you want to spend on each roster spot.
    • Do your research: If you want a top 5 RB, look on some other league pages to see what % of the cap usually goes to that specific type of player
  • Don’t ignore the scoring rules
    • Some leagues put a premium on TEs, while others have the same number of points for all offensive players. Pay attention and allocate funds appropriately.
    • For leagues where all defenders get the same points per tackle, go after linebackers and safeties that are known tackling machines. It’s hard to predict interceptions and sacks but it’s a lot easier to predict what players are likely to get a lot of tackles.
      • Unless you are targeting J.J. Watt or a top defensive lineman, I would recommend spending more of your salary cap on linebackers and the secondary.
    • Build a balanced team
      • Some people go into these auctions trying to get as many top tier players as they can afford and it rarely works in their favor. Nine out of ten times, a balanced team with only a couple studs will beat a team with five studs and a bunch of scrubs.
sample roster strategy

sample roster strategy

Step 3: Stick to Your Budget

One mistake people often make when the auction begins is they start to stray away from their strategy. You spent a lot of time putting together this plan of action so don’t forget about it the second your #1 target goes above your allocated cap space for that position. The worst thing you can do is throw away all your hard work because another team values a player more than you do. This is why I recommend having a backup strategy and a backup to the backup strategy for all your targeted players. Everyone always wants as many studs as they can get, but remember, the most balanced team will win practically every year.

In my league I really wanted Matthew Stafford as my starting quarterback. The league rewarded 6 points per touchdown as oppose to the standard 4 points, so I knew this position had extra value. I planned to allocate 12.5% of my salary to this one spot ($11 million), and just my luck he went for $11,450,000. My backup plan (Andrew Luck) had already more than surpassed that number so I went after my third target: Ryan Tannehill. Not only did Ryan cost me only $7.4 million (8% of my salary cap) allowing me to spend more money on RBs and WRs, but he ended up outperforming my #1 target on the season:

  • Matthew Stafford – $11,450,000 – 312.6 points
  • Ryan Tannehill – $7,400,000 – 347.2 points

Another thing to keep in mind if you are losing out on all the top players is to look at your roster by dollars per point. In my league after losing Stafford the next stud I went after was Matt Forte. I again was willing to spend $11 million dollars (12.5% of my total salary cap) for him and my research paid off as he got bid up to exactly $11 million. However, another running back in my league (Darren Sproles) went under my radar and was won for $4.9 million dollars. If you look below, that owner actually got a better value because I was too focused on going after a stud running back (feeling slightly jaded after missing out on Stafford). This is why a budget is important because if I passed on Forte, I could have gotten two equivalent players to Sproles and ended up with more points in the end.

  • Matt Forte = $11,000,000 – 350.6 points – $31,375 per point
  • Darren Sproles = $4,800,000 – 180.4 points – $26,608 per point.
sample player salary cap plan

sample player salary cap plan

Step 4:  Don’t Be Afraid To Admit (and fix) Mistakes

My biggest mistake this past season happened in our first auction. I didn’t read the scoring rules carefully enough and I wasn’t paying enough attention to tight ends. If I had read the point system more carefully I would have realized that tight ends received more points per reception than any other positional group. By the time I realized this I had budgeted incorrectly for the entire position and all of the top tight ends had been taken. At this point I took the best tight end left available and went to work.

After some research and talking to a few other owners I was able to work out a three team trade to help fix my mistake. I moved my recently acquired tight end to another team who missed out on the position in exchange for a low level draft pick. I then turned around and traded a higher level draft pick of my own for Delanie Walker and a few other supplemental players. The message here is don’t be afraid to admit when you are wrong, but at the same time don’t be scared to try to right the wrong. My punishment for not reading the rules cost me a degradation in a draft pick, but my reward of $1,000 at the end of the season more than made up for it.

Step 5:  Spend All Your Money

Another area where I saw a lot of people struggle is they tried to save money and didn’t use a majority of their cap space. Their reasoning was it helped provide flexibility for the future. The reality is it caused some of them to miss out on improving their roster. While there is nothing wrong with trying to build for the future and save cap space along with draft picks, that’s not what this article is about. This article is about winning now. Since I won $1,000 in a league that only costs $50 a year I can basically play in this league for free for years. Why play to win in 5 years when you can play to win today?


Use Fantasy Football to put extra money in your pocket!


That being said, I don’t believe anyone should just ignore the future. While I spent all my money this past season, I also was very selective in moving draft picks. By winning a few young quarterbacks in the auction (fantasy football gold in a 32 team league), I was able to trade them for first round picks and now have 3 first round picks over the next two years as well as I have the #5 overall pick in this upcoming rookie draft. This is why it’s important to spend all your cap space in the auction, because you don’t want to have to trade away draft picks after the auction when you miss on some key players.

Another way to spend all your cap space without risking your future is found in good contract management. Sign some of your high risk players to one year contracts so that next year you will lose these players and have money to spend in the following auction. For me, I did this with Frank Gore. I spent over $5 million on him, exactly what I budgeted for, but knowing he was on his last legs I only gave him a one year contract. Now for 2015 he is no longer on my roster and I used the extra cap space to acquire and afford the aforementioned Darren Sproles to fill his spot.

Step 6:  Play the Waiver Wire

Once the auctions are all done and the season begins, remember that you can always make your team better. There is always room for improvement, and you may need to fill for players going on IR. To win a fantasy football league you should never feel content with your team and should always be trying to make it better. For me, my biggest weakness at the beginning of the season was found in my secondary. I went into the season with Chris Conte as one of my starters who after week two started to underperform. Based on his performance I decided to go out and sign the best free agent safety from week three. In came Kemal Ishmael from Atlanta. On a salary of $750k (less than 1% of my salary cap) he became my second highest scoring defensive player by the end of the year. He also put up double digit points in seven of his final eight games. All from a guy I found on the streets in a very deep league. This is why I recommend you always play the waiver wire, because you never know what gems you may find.

Step 7: Just Win Baby!

As much as I would like to guarantee everyone who reads this article will win their fantasy football league, we all know that is not possible. However, what I can promise is if you take the above steps to heart that you will be ahead of half of your new fantasy football league before you even start your first auction. In my league I took a survey and found out that less than half of the teams had a fully thought out strategy before our first auction. I recommend if you want to win a lot of money, you be one of the teams who do.

League Trophy

Become a Fantasy Football Champion!


At the end of the day, the one thing I know is that fantasy football is one of the only places where a $50 bet can give you a 1 in 32 chance at winning $1,000. Trust me, that’s a gamble I’m going to take over and over again.

Good Luck!


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