I play fantasy baseball because I love the game of baseball. I can’t get enough baseball. I’ve tried. I can’t do it. If you know, you know, right. Still, many fantasy ballers play the game because they like the competition inherent in fantasy contests. Make no mistake, fantasy baseball can be hard. A 162-game season, 30 MLB teams each with a 40-man roster – the permutations of fantasy rosters is nearly endless. To have a Captain Obvious moment, let me say, it isn’t easy to win a competitive fantasy baseball league. Of those who have won leagues, we know they worked hard to hoist their trophy at season’s end. If you’ve done that, you’ve got a taste for it and want to do it again. If you’ve not, well, likely you’re craving the experience.

To win, you have to have some luck. I’ll get that out there right now. But I believe in making your luck whenever possible and that’s where strategy comes in. That’s what I’m going to start talking about here. Strategy to win leagues. And the nuance of strategy. The devil really is in the details of managing your team and I think that starts in the selection of your team.

Let’s start with this agreement. For whatever the reason we play fantasy baseball, we all play to win. With that as a primary agreement, let’s move on to some techniques for how we might put ourselves in better positions to win.

This is my first article on this platform and my first article about fantasy baseball on any platform. And what’s the expression? No, not the “you never forget your first time,” though that’s true too and even applicable but I’m talking about the axiom “you never get a second chance to make a first impression.” Well here goes folks, for me this is my first impression. And wouldn’t you know it, day one, and this article being job one, and I’m already impaled on the horns of a dilemma.

Many dilemmas actually. I mean a lot of times as a player myself I go looking for fantasy baseball information with the hope that someone will tell me who to pick between x and y player. I hope someone, if I’m being honest, will tell me exactly how to build my roster so that it runs itself right into the playoffs and in the process makes me look like a savant. Well, in spite of all the really great advice I’ve read or listened to, I haven’t found that magic bit of content that empowered championship runs. But I’ve found a lot of great nuggets of information that gave me an advantage. So rather than try to give you what I cannot – infallible wisdom – I’m going to share a process for making decisions that I’ve constructed from reading and listening to great baseball and fantasy minds over the last two decades.

So let’s start with a simple question – a simulation if you will. You’re drafting and it is your pick: Who ya got:

Andrew Painter or Eury Perez?

I mean they’re both destined to be stars right? Right! Check.

And both are on the board and it’s my time to make a pick in my first-year dynasty start up. So, I have to ask: Who do I pick? Who do you pick? And why? The why is important. Very important. Let’s think about it.

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