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Why we Play Fantasy Baseball & Why it Matters

Fantasy baseball is a wonderful, crazy world, but we also all play the game for different reasons. The other week Chris Clegg and I were on the Commissioner’s Office and we talked about how fantasy baseball is -and should be – first and foremost about fun. This is certainly how I think of fantasy and how my story of playing fantasy to now writing about it here.

Things look bleak now but there will be baseball in 2022! Why not get a head start and jump in a Fantrax Classic Draft contest? Get a jump on the season with a Best Ball league or maybe a Draft and Hold. Or put some green on the line with a new season-long league to try and conquer. There’s no better time than now to get your baseball on!

My Fantasy Origins

My first fantasy baseball league was when I was in high school – on mlb.com… The next league I did was on yahoo and it was a public league and a league with some friends and family. These leagues were jokes – playing against people who didn’t really care or didn’t pay that much attention to baseball.

The next step forward was a league with the infamous FSAA (may he rest in peace), taking over a team as I entered into the amazing world of dynasty.

That launched my path from playing and loving dynasty baseball to writing here, running a commissioning service, and podcasting… but why I got into all of this was the love of baseball and for fun.

Love or Money?

This will probably come as a surprise to most people, but it wasn’t until the 2021 season that I put any money on my fantasy leagues, and I still play in some free leagues, because I don’t play to make money. Do I enjoy winning money? Of course – but I also just love the competition, and more importantly, I love the friendships and relationships that have been formed through fantasy.

Before FSAA (Tom) died last year we texted almost daily, and there are a number of other relationships that have been birthed out of fantasy baseball. This is also a big part of why I started the Fantasy Baseball Commissioner, and, as a member of a number of my leagues dm’ed me a little why ago, it looks like it’s working:

“btw – in case you don’t hear this enough, just wanted to say thank you for the community that you’ve created – or gave a space to and fostered.”

Which gets me to the point of the article.

Why people play. Now – these reasons don’t need to be separate or distinct – you can play for fun and money, you can play for just fun, you can play for just community, you can play for just money – but you need to know why you are playing.

If you are playing just for money (or you know others in your leagues are), then this will change league dynamics. For leagues like best ball leagues that’s one thing – given that all of those leagues don’t have trades and claims, etc, winning the league and winning money are clearly in line with each other. Moreover, since best ball leagues don’t really prompt much interaction, those leagues really are about two things: having the fun of drafting without in season management and winning money. I know some players play best ball in mass to diversify investments and play so many that it’s really just another piece of their investment portfolio – it’s not why I do best balls, but it’s a reason.

In redraft leagues, the intent is obviously also to win the league every season, so if a league is a paid league, then winning money and winning the league go hand in hand. Which, if you’re like me – a lot of having fun in fantasy is about winning. So – in those leagues you can have fun, make some trades, be aggressive, and try to win some money. We’ll come back to trading in a minute.

However, in dynasty leagues – having fun and building relationships is a whole different ballgame and part of why I love dynasty.

The fun: there are a number of ways to have a ton of fun in dynasty leagues and dynasty builds without being a contending team, be it a rebuild or otherwise.

The relationships: Because of the trading and long-term makeup of a dynasty league, getting to know people and getting to talk trades and relationships is a great part and one reason I love it. You get to know people, not only because you want to make trades to improve your team, but also because getting to know people is just a great thing about dynasty and life.

Now – thus far the motive for playing (assuming everyone’s goal at some level is to win) hasn’t really impacted much – but now it does. Indeed – it can also vary from league to league for a person.

If you are in an industry or shark or something like that league, even if you primarily play for fun, you can expect trading to be far more about “winning a deal” than ever caring about a fair trade. For example, I play to win in all of my leagues, be it for money or not, and no matter the league I am certainly never trying to pull one over on someone in a trade or take advantage, but if I’m in a league with other writers or industry managers, I’m both more expectant of it with other teams, and less reticent to do it, than if it’s a home or friends league. The makeup of the managers in the league and the overall competitiveness of the league changes the math on that for some managers, AND, even if it doesn’t for you, you better be aware that it does for others and be ready to make trades with them, compete with others, or accept that you are going to see deals made that you see as absurdly lopsided.

Side note: Sometimes trades in dynasty leagues will look lopsided based on perceived market value, but the reality of dynasty trades, just like trades in MLB, is that sometimes the immediate look of a deal and the long-term look are not always the same.

Secondly, if you know you are playing against someone who is in it for the money ONLY, then you need to approach trading differently

In redraft of course everyone is (or should be) going for it all the time. BUT be it redraft or dynasty, the person who is in it only for money (or if they are just in it to win the league at the expense of some of the relationships, even in a home league) they may make deals that destroy the competitive balance of a league. While this isn’t ideal for the longevity of a league, you can’t really fault people, at least in most leagues, for going for the jugular. But, as I mentioned before, you need to be aware of it as you engage in trades and make your own choices.

There is not necessarily a “right” motive for playing fantasy, but I sure think it is better if at its heart is a love of baseball and enjoyment of playing the game. There are “wrong” motives – if you are playing in a league to tear it apart, manipulating a roster to hurt members of the league or anything of that nature, you should not be in the game. If you are playing to win and make money – that’s fine. If you’re playing to have some fun, make some friends, and maybe make some money – that’s great. If you’re just playing for fun and a little distraction and hobby – that’s good too. Just don’t play to destroy things or other people – because a lot of people are doing this for, at least in large part, fun.  So as you join leagues and draft this spring – ask yourself why you’re doing it – and be aware of why your opponents might be doing it as well.


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