Playing For Keeps: Managing 2020 In A Keeper League

In this week's edition of The Friday Meta, Kyle Bishop weighs three different approaches that keeper league owners could take toward the 2020 fantasy baseball season.

Something you've probably heard from many in the fantasy baseball community - including yours truly just last week in this space - is that you'll need to be ruthless in managing your squad(s) this season. With 102 fewer games than we're used to, there's precious little time to waste waiting for a player, no matter how talented, to get going. More than any other season, fortune is likely to favor the bold.

Simple enough, right? Kill your darlings, as Faulkner once said. Terminate with extreme prejudice. Cut that bum and don't look back. Be brutally unsentimental. Good talk, now let's watch the game.

That's all well and good in redraft leagues, where your roster decisions only impact the current campaign. But in keeper formats where one wrong move could have you kicking yourself for years, how do you reconcile the aggression that the moment demands without completely ruining your future? Or is it worth risking such a decision when the race for the prize is as wide open as it probably ever will be? The way I brain it, you have three paths from which to choose.

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Stay the Course

With this strategy, you don't deviate much from your modus operandi - at least not in a way that reverberates beyond this aberrant season. Go ahead and punt a category or change it up with your moves on the margins, but make no roster decisions that drastically impact the future. No win-now trades, no non-fringe assets thrown on the chopping block  simply for having a rough week. Just ride it out with the core you've assembled and hope it works out. If not, transfer that hope to "hoping that we have a full and reasonably normal 2021 season."

Shoot the Moon

Typically, the fantasy baseball season is a marathon, not a sprint. That's certainly not the case in 2020. There are a number of logistical challenges to managing a fake baseball team this year, but it's theoretically never been easier to win a championship because you only need to do well for two months. Anyone who's played this game before can recall plenty of times either they or their opponents put together a red-hot stretch in an otherwise unremarkable season-long performance. Chaos tends to breed parity because anything can happen; much as the arc of history bends toward justice, the arc of a 162-game season bends toward players, teams, and even fantasy owners who are more talented.

Why not take advantage by pushing your chips in on this year? Flags fly forever, after all. And while some may place an asterisk by any 2020 title, you can make the argument that navigating the absolute madness of a pandemic-wracked season and adjusting your management style accordingly reflects pretty damn well on your abilities. Also, consider the type of person who typically assigns asterisks to things. Do you really care what they think? And with where things seem to be headed (not just with COVID, but with the looming labor strife that seems certain to be apocalyptic in scale), all we really have is now.

Thread the Needle

Are you not swayed overmuch by either of the above approaches? Then hedge your bets. Don't bet the farm or blow things up, but feel free to take a couple of moderate to large swings and see what develops.  You can make moves that are consequential, but stop short of being seismic. The foundation can remain intact while you remodel a few rooms, so to speak.

There's no fun in simply going through the motions and writing off an entire season, truncated and precarious as it may be. You invested time and perhaps money into this team already, so you may as well compete hard despite everything. At the same time, it'd be a tough pill to swallow if you mortgaged the future for a two-month season that didn't even result in eternal glory.

The Friday Meta is Kyle Bishop's attempt to go beyond the fantasy box score or simple strategic pointers and get at the philosophical and/or behavioral side of the game. It is hopefully not as absurd, pretentious, or absurdly pretentious as that sounds.

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