Finding My Fantasy Football Winning Strategy

A true story of going from a fantasy zero to a hero. The Bear makes his RSJ debut and discusses the change in mindset that's led him to fantasy greatness.

Up until 2014, I hadn’t so much as made the playoffs in my league.  I was floundering along aimlessly in hope that something would click and I’d magically start winning.  I had such little confidence that I had my younger brother draft for me one year- talk about swallowing your pride.


Sick of my permanent residence in the league basement, I finally reached out to an old friend for some guidance.  You know him as “The Wolf.”  The Wolf and I decided to breakfast at our favorite spot, Red’s Kitchen in historic downtown Salem, Massachusetts, and discuss general fantasy strategy.  I trusted him, not only because he is one of my oldest friends, but because his fantasy record spoke for itself.  He had multiple championships under his belt at the time and was typically runner-up if he didn’t win. Plus, the guy’s so addicted we couldn’t sit through Game of Thrones without him doing a Death and Kill draft.

He changed my fantasy outlook and fortunes that morning.  I went from wanting to throw in the towel to developing an almost brash confidence about this new methodology.  Though we may end up with vastly different teams for reasons I’ll explore later, the lens with which we evaluate and invest in players is the exact same: as if they are stock and our teams are point producing portfolios.

Just like the bigwigs on Wall Street, evaluating the floor and ceiling of your investments (the players), and trying to create a solid balance of upside and safety, is paramount. The floor is how your player is going to perform on his worst week.  Still nursing the hammy?  Problems in the locker room?  This guy is STILL good for 9.  That’s his floor.

The ceiling is his uppermost limit.  For example, we’ve seen Drew Brees throw for 50-plus touchdowns.  Can he do it again?  You bet your fantasy butt he could!

So how do you figure these out? Okay guys, this is where it gets a little tricky.  Stay with me.  What you want to do is take the average weekly points for each individual player, find the standard deviation and multiply it by the number of players on your team.  When you are done with that take the square root of…
Just kidding. tumblr_mg45duweq51ql5yr7o1_400

Calculating ceiling and floor is actually quite simple, fellas.  I only look at a couple of numbers and factors, thanks to The Wolf.  At its core, a players fantasy success or failure involves the combination of five factors: talent, opportunity, coaching scheme, surrounding talent, and risk. The Wolf goes into far more detail here, but considering all these factors has helped give me a holistic, subjective view of all players.

The end goal, of course, is to put out the highest scoring team every single week. This means coming up with the appropriate balance of boom or bust (high ceiling, low floor) and reliable options, even if their ceiling might not be game changing. Exactly how you balance out the upside versus the safety is personal preference, is where The Wolf and myself really differ, and why I am titled The Bear.

To follow the stock market analogy, my approach is much more bearish than our fearless leader, meaning I am a more conservative.  I typically won’t draft unproven rookies before the eighth round, I err on the side of caution and guaranteed points when setting my lineup as opposed to gambling on big upside…you get the picture.  If we were investing, I’d put my money in the companies (players) with long-term track records of success who manage their business well and stay out of trouble… even if they lack that “explosion potential.” While The Wolf is out chasing ceilings and getting chubs for unestablished “potential,” I personally hunt for high floors that are near locks to yield.

This sets up some serious debate. As such, while The Wolf releases his rankings (which are bound to include a few curve balls with him), I’ll be providing a voice of reason with some Risk Assessment follow ups. We’ll also get some Player X vs. Player Y arguments going.

Despite these philosophical differences, the stock market backbone to our drafting has still afforded us both tremendous success. Like I mentioned, after previously never making the playoffs,  I have taken $1,500 to the bank via a 1st place 2014 and a narrow 2nd place finish last year.  David Johnson absolutely screwed me with 43 POINTS in the championship week?!  You gotta be KIDDING me, man.  Especially since I dropped him earlier in the year.  I digress.   In all seriousness, I don’t mind getting paid every year right after Christmas. The most wonderful time of the year is even more cheerful with a fat check in the back pocket.

What’s been most valuable, beyond just the cash, is the empowerment as a fantasy owner. Here’s the problem with so many owners:  there are too many people in national media with an opinion and if you listen to all of them you’ll be confused. And confused owners lose every week.  You need to know the right way to approach things, and make the decision yourself.

Otherwise, you’re the guy that asks every single person in the office, “Hey should I start John Brown or Malcolm Floyd?  I can’t decide.” And then after hearing 16 different opinions you call your cousin’s friend’s freshman year roommate Vin as your swing vote. Don’t be that guy who calls Vin (although I love the enthusiasm there, Sparky, and thanks for the donation!)

mrw friend hd phone drop

If you don’t follow a process and set of principles, you are going to continue guessing.  Guessing doesn’t win championships.  Keeping it simple, with a core set of rules and regulations to guide your gut feelings, is what truly works.

While this stock market angle and balance of floor and ceiling are the most resonant of all his philosophies, I’ll leave you with a few more of The Wolf’s lessons that I’ve picked up along the way.

Here are the basic tenets of the Wolf’s methodology that I believe to be most important:

1) When it comes to drafting, almost always wait on QB.  There are high value guys that end up going in the 8th round or later all the time.  I got Brady in round 10 last year when he was still suspended.  He ended up doing okay.  Same thing with Russ Wilson the year prior.

2)Pick up back up running backs.  Injuries at the RB position are so common that you might as well be ahead of the game and pre-empt the injury. When out of options, go for the the backup running back with the highest ceiling.  Note – these don’t have to only be handcuffs for your starters, but the guys who’ll offer the most value should the starter go down. Think DeAngelo Williams in Pittsburgh or Darren McFadden in Dallas — guys who’ll provide quality starter status if thrust into the lead role.

3) Just because you know better than to reach, don’t underestimate the importance of a good defense and kicker. Personally, I try to get Gostkowski every year and have for the past two.  Guy’s automatic. Yes, there’s so much variability in general at “the fantasy special teams,” making streaming and playing the match-ups easier here than anywhere else. Yet, if you can save the waiver budget and attention by having locked-in weekly options, it can payoff big.

In closing, I am a huge advocate of this site and encourage each and every one of you to subscribe to learn more from The Wolf. I promise you that it will pay off every year.  You couldn’t have a more passionate guy driving this project and you will all realize how lucky you are when you are cashing out your Venmo account a few days after Christmas next year, just like I told ya!  Take the stress out of your weekly fantasy decisions by developing a process that increases your win probability exponentially.


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