The Idiot’s Guide to In-Season Fantasy Baseball Management: Part 2

Last week, I wrote a long-winded intro about my days as a chess player. In chess, there are three stages of the game. There’s an opening, the middle game and the end game (preferably, a checkmate). Instead of writing another intro for Part 2 of this series, I’ve decided to give you the CliffsNotes version as a refresher.

Managing a fantasy baseball roster doesn’t start and end with the draft. You can post as many draft boards on Twitter as you’d like. Some may get oohs and aahs in the comment section. Yet I’d argue the person with the best-looking draft and the person with the worst-looking draft have equal opportunities to close out the season with a fantasy baseball title.

For every roster that looks like Tom Cruise, there’s a roster that looks like Sam Cassell. Sorry Sam, hopefully he doesn’t read this. 

This might be a hot take. But I’d rather inherit the worst-looking roster if I knew I was handing it off to a shrewd manager – as opposed to inheriting the best-looking roster but handing it off to someone who takes a more passive approach at in-season management.

Winning in fantasy baseball is all about the collection of moves you make on a daily, weekly and season-long basis. For every action in nature, there is an equal and opposite reaction. Sir Isaac Newton famously surmised this law of motion back in the 1700s. I can assure you it came shortly after bidding too much money on some flash in the pan during his FAAB period.

In case you missed it, I crafted my first four rules to The Idiot’s Guide to In-Season Fantasy Baseball Management last week.

Below, I’ll go through the final four steps to help you close out a fantasy baseball championship.

Step 5: Don’t abuse the trade

I realize not everyone plays in the NFBC. I got my feet wet playing in a home head-to-head points league back in 2011 that still runs today. In many home leagues, trades are an essential part of the league’s identity. Take my league for example. No one has made more trades than I have since the league’s inception. Part of the reason I’m writing about this step is for my own good. I should follow my own advice.

Don’t abuse the trade. Trading can be an extremely useful way to upgrade your roster and address weaknesses. It can also be a forbidden fruit that slowly tears down your roster without you noticing until it’s too late.

You don’t need to treat your team like a carousel. Just because a player has a bad two weeks or goes into a slump doesn’t mean you need to make a change. In fact, trading from a position of weakness is one of the most common mistakes players make.

Never attempt to trade a player who’s slumping. You’ve automatically devalued them by doing so. Instead, you should shop players who are currently on a tear. I know it doesn’t feel good to part ways with someone who just won you a week. But ask yourself, is this sustainable? If not, their value will never be higher, and the return will never be greater if your opponent decides to pull the trigger on a deal.

Be careful, though. If you execute this type of shrewd move on more than one occasion, your leaguemates might start getting skeptical anytime you float a player who’s popping off during a trade negotiation. Don’t trade because you want to. Trade when you have to.

That leads me to my next point.

Step 6: Study your leaguemates

Winning in fantasy sports is mostly done through three pillars. Skill, luck and psychology.

Nothing fascinates me more than psychology. Not the actual field of psychology, but psychology within your own league. Not every member of your league is like Pavlov’s dog, but the more you study your leaguemates, the easier it is to pick up on their tendencies.

Once you know your leaguemates as well (or better) than you know yourself, the easier it is to make decisions, negotiate trades or make proactive moves before they do. I already gave you an example above. I trade like a madman in my home league. Always have. I’ve sold high and bought low more times than you can imagine. It’s worked for me for nearly a decade and I have three titles to prove it. 

But people are starting to catch on. Last year, I executed the fewest number of trades in a single season in the league’s existence. I’m not trying to pat myself on the back. In fact, quite the opposite. I should have paid closer attention to what my opponents were saying to me after our deals went through. I should have paid closer attention to what they were saying to me during the negotiations.

It became clear after a while that people were exhausted and didn’t want to trade with me anymore. Or, if they did want to trade, they would ask for more and more in return based on results from past deals. Fleecing someone (fairly or unfairly) might work out for you in the short-term. But in the long-term, it’s only going to push that person farther away from the table. Or they’re going to apply a trade tax to any deals you make in the future.

I like to joke with my leaguemates that the reason I never accept trade proposals anymore is because they are applying an “Adam tax.” They want more than what I’m offering because they are afraid I might know something they don’t. Many of my leaguemates have become smarter over the years. The league is getting more competitive – because like I’ve been doing to them for nearly a decade, my opponents are starting to study me and pick up on my tendencies as well.

Don’t underestimate how important it is to know your leaguemates. Not everyone has a poker face. Make sure to exploit that.

Step 7: Learn how to close

I teased this last week. You can do all the right things during the season, but you still have to close out a championship in the final few weeks. In the NFBC, that might mean benching a stud player who’s at risk of getting extra days off in the final week of the season. It might mean benching a second-round pick who’s gone in a major slump in favor of a September call-up who is tearing the cover off the ball trying to win a job next season.

In those final few weeks of the NFBC season (or any league), don’t set your lineup based on name value or draft value. Last year, knowing Albert Pujols was chasing 700 career home runs down the stretch, I plugged him into my lineup in the utility spot late in the season knowing A) He’d be in the lineup every day without fail, and B) He was swinging for the fences. 

Was Pujols the best player in my lineup or on my bench? No. But did it help me stay near the top of the standings in the home run category? Absolutely. From Sept. 4 through Oct. 4, Pujols slashed .276/.341/671 with 9 homers/27 RBIs. 

He had motivation to perform in the final 3-4 weeks. To close out a championship, you need to assess your roster on a more day-to-day basis rather than from a season-long lens. You don’t need to “start your studs” if your studs aren’t the best options in that final week. This is a very important point that can make the difference between a first-place trophy and the runner-up spot.

Step 8: Take a break

I’m not sure if this final point is just my own preference. When the fantasy baseball season ends, whether it’s with a title or in dead-last place (hopefully not that), I like to shut my brain off and shift my focus elsewhere. 

I know there are some freaks out there who are strategizing for next year the moment the final pitch is thrown during the current season. My colleague Jeff Ratcliffe famously talks about the fact “there’s no offseason in fantasy football.” Maybe that’s true for some people, but it’s more beneficial in my opinion to take a much-needed break. I’m not saying you need to go full Aaron Rodgers and go on a darkness retreat. Just clear the mind a bit. 

I’m going to be honest, I’ve written eight articles during the offseason on how to approach the 2023 fantasy baseball season. Yet I still haven’t participated in a fantasy draft. Gasp. I know, it sounds bad. But that’s just how I like to approach the fantasy baseball season. I like to shut my brain off from October until early-mid March. Once Selection Sunday happens and the NCAA basketball tournament bracket is revealed, I really start ramping up my preparation.

By late March, I crank out drafts. I like to tune out the offseason and Spring Training noise as much as possible. Inevitably, players who launch a few home runs in the spring are going to shoot up the draft board and gain some steam. Remember, every action has an equal and opposite … yeah, yeah. 

I feel at my best when I enter my drafts in late March with a clear head and a few weeks of preparation. Would more preparation help me during the draft? Perhaps. I’m not sold one way or the other.  However, I know the draft isn’t the end all be all. See how we circled around to that again? I’m confident that entering the draft with a clear mind will take the pressure off me during the offseason to get every player right. And once I have my draft board in hand, I take a step back, assess it and plan out how to manage my roster in-season (using this two-part series as a reminder). 

Selection Sunday is in two days, which means it’s nearly time for me to start my own fantasy baseball drafts. I hope you found this series and helpful as I did writing it. I just hope my leaguemates don’t see it. Tyler, I swear that trades section wasn’t about you.