Fantasy 101: Why We Play Fantasy Baseball

In light of all the heavy analysis we do, Dave Cherman takes a moment to remind us why we play fantasy baseball.

I sit here writing this on the Monday following Week 15 of the fantasy football season. This will be posted much later, but I wanted to give you an idea of my mental state right now. My one team that actually made the playoffs has just gotten eliminated by a whopping margin. This day comes in every fantasy season. When I look back on football season, I ask myself a number of questions: “Why did I do this? What did I get out of this? Why did I spend four to five months of my life obsessing over this?”

I’ve won a fantasy football championship before; it was fun. I got to feel superior compared my friends and rub it in their faces. But I’ve grown tired of it. Fantasy football is easy. It’s almost as much luck as it is skill.

Today is also a holiday for me. It’s the day I stop thinking about football and start to go back to my first and deepest love, baseball.

I played fantasy baseball for the first time in 2007; I was in a league with some friends from middle school that lasted for four years. I have a distinct memory of trading Josh Beckett for Ubaldo Jimenez on draft day in 2010 and it paying off in a big way. After that season, we lost a few people and the league fell apart. I didn’t play again until 2013, when I joined a college friend’s keeper league. I didn’t watch a ton of baseball during those two years and, as a result, I goofed up big time. I kept a 23rd-round Aroldis Chapman instead of a 23rd-round Paul Goldschmidt, and I paid for it. I dropped Jose Fernandez in that same season. I topped out at fifth place in 2014 before being replaced.

I joined a few other leagues over the next few years, trying to scratch that itch and improving each season. I’ve since won a few leagues, as I’m sure many of you have. I’ve also missed the playoffs a few times, including this year in the Pitcher List staff league.

Why is this relevant? Most of us have a love story with fantasy baseball that goes back years or even decades. We can all remember the first time we played this wonderful game, and we remember all the highs and lows. Each of these incidents is a notch in the belt that no seasoned fantasy veteran is without. Our mistakes make us stronger, make us smarter, and, each year, bring us back to the draft more determined than ever before.

I’ve played fantasy basketball, hockey, football, and baseball; there is NO fantasy sport as difficult as baseball. There is no sport that requires quite the extent of daily attention and focus for such a long period of time.

It’s a grind. No amount of lucky drafting can win you a fantasy baseball championship. It takes scouring the waiver wire each day. It requires diligent observation of your pitching staff on a daily basis, lest you bench Max Scherzer vs. the Marlins. In the hardcore leagues, it takes even more research to try and get the slightest advantage. In most sports, it’s about drafting the right player. In baseball, often those players have to be discovered before they even get the playing time.

Fantasy baseball is hard. That’s just a plain and simple fact. But what makes it harder?

A fantasy football draft lasts typically 15 rounds while the regular season lasts 13 weeks, with players playing only once per week. This means three things: One, a draft can make or break your season. In one league, I missed on my top three picks, and it didn’t matter how good the rest of my team was — there was no coming back from it. While the waiver wire is important, chances are, all the fantasy-relevant players were drafted, which is far from the case in baseball.

Two, a short season means more variance. If a player goes through a bad stretch in baseball, there’s time to recover and build the rest of your team around it. In football, a bad stretch by one player means you’re probably going to bench him and risk missing out on his renaissance or cut him completely. No guessing game should have that little room for error.

Three, the small lineups and limited number of games means that a single player can win you a week, and that’s beyond boring. I want a fantasy sport that requires you to put a whole team together. We all want that; it’s just better and more fun that way.

So we’ve established fantasy baseball is tough. So why do we play it?

We play fantasy baseball because the pinnacle of accomplishment demands the highest levels of difficulty. Winning your fantasy baseball league means you grinded, pushed, and strategized better than your friends for seven months to achieve the highest honor. It’s possible to win fantasy baseball by being extraordinarily lucky, but, for most, you have to comb through the otherworldly amount of statistics, and you have to comb the waiver wire because it’s not enough to have the highest waiver priority when Dalvin Cook gets hurt.

We play fantasy baseball because it gives meaning to a Tigers-Blue Jays game in September. There’s nothing quite like watching Joe Jimenez give up a leadoff walk in a one-run game in the ninth, knowing you need a save to seal the win, but Danny Jansen, who is on your opponent’s roster, is on deck and a two-run homer gives him the win.

We play fantasy baseball because no other sport features such an extraordinary amount of statistics that somehow simultaneously tell us so much and so little. Who among us can deny falling down a FanGraphs rabbit hole or suddenly realizing you’ve spent three hours on Baseball Savant because you saw something odd in Nomar Mazara’s batting profile?

We play fantasy baseball because baseball is our pastime. It’s a beautiful game that, without fail, inspires the complete love and adoration of anyone who gives it the patience it deserves.

While writing this article, I decided to go back through my Yahoo history and look at every team I managed. Each one brought a smile to my face, even my 10th-place finish in a keeper league in 2015 because I remember the fun trades I made. My favorite trade involved a guy from Chicago who I’d met through this league. When the league folded, he joined my upstart keeper league in 2017. Earlier this year, we met in person for the first time.

Fantasy baseball gave me that. The joy of playing brings people together.

When I get to this place in baseball, the Monday after I’m eliminated from my final playoff matchup of football season, I often ask myself the same questions that I ask myself today. Only, the questions are a lot easier to answer because, with fantasy baseball, it’s about the journey, and the journey will always be worth it.

Featured image by Justin Paradis (@FreshMeatComm on Twitter)

Dave Cherman

Across the Seams Manager, also a former player and umpire and New York-based lawyer who spends his free time studying advanced statistics and obsessing over fantasy trades. Will debate with you about most anything.

3 responses to “Fantasy 101: Why We Play Fantasy Baseball”

  1. Cameron Kirkpatrick says:

    5×5 with OBP & QS with 5 keepers.
    My keepers are Betts, Lindor, JRam, DeGrom & Clevinger (I know, right?).
    I’m wrestling with my first pick in the draft. I’m drafting third, so a few of the names available will be Pham, Giolito, Albies, Nelly, Villar & Muncy.
    Should I be going towards Nelly’s power? I’m seriously considering Giolito, because I think everyone’s going to wait on pitching- and I don’t necessarily want to follow the crowd…

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