Kyle Bishop offers his thoughts on how to fix a broken fantasy baseball league, using his own as an example

Coming into last season, my home league of 13 years had a problem. Since becoming a rotisserie league, adopting an auction draft, and instituting a new keeper system six years earlier, only one person had won it: Me.

Let me state up front and unequivocally that I don’t intend or want for this article to be hundreds of words of bragging. You don’t want to read that and I don’t want to write it. Besides, you don’t win a league for six years running without considerable luck.

Case in point: The first year, 2011, was the year of the twin collapses of the Braves and Red Sox, each of whom entered the season’s final day needing only a win to make the playoffs but instead lost in devastating fashion while rivals won to knock them out. While that insanity was going on, I was glued to StatTracker, watching impossibly thin margins fluctuate. Ultimately, after multiple tie breakers, I had completed a 14-point comeback in the final two weeks and edged out my cousin for the title. This is the reason why if anyone mentions Ted Lilly, a grateful tear comes to my eye. (No one ever mentions Ted Lilly.)

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The next year was much less eventful and produced another narrow but undramatic win. For the next four years, though, the margin of victory grew. Every spring, I figured the keeper system ($5/year inflation on draft cost, with a cap of $180 on keepers (60% of the overall $300 budget) would finally do what it was designed to do and keep me from winning again. Another owner had finished second multiple times and been a strong contender every season; I always expected this to be the year he finally got past me.

As the 2016 season entered its final month, I posted my usual thread on the league discussion board, posting my proposed rule changes and inviting ideas from everyone else. I wanted to expand from from 10 to 12 teams and to bump dues from $20 to $25. The first response from a leaguemate was blunt: “This league is pretty broken right now.” He pointed out that the bottom feeders had checked out long ago, so why should we expand?  He added that it was a bit presumptuous of me to propose a dues increase when I was cruising to a sixth straight win by my largest margin yet.

I didn’t disagree with much of what he had to say. In fact, the changes I had suggested were what I hoped were solutions to those same problems. In my view (Tim McCarver’d), there were four major areas to attack, and they’re easily applicable to other leagues and the various ways in which they might be broken.

Make Your Fantasy League Better

1. Trim the fat.

I wanted not just to expand the league, but to remove a notoriously absentee owner. While he was and remains one of my best friends, he just wasn’t participating much after the draft – during which he’d often entertain me with troll bids and other shenanigans. It was fun to hang out together while we drafted, but he put no effort into managing his team and had to go.

Unfortunately, there was a second  and unexpected departure of an incumbent owner. My cousin told me after the season ended that he was bowing out. Only three people, me included, had been around since the league’s inception in 2004, and he was one of them. But he just didn’t have the time to devote to the league anymore, and he pointed out that his recent results were indicative of that. It was a bummer to lose an original member, but it presented an opportunity to improve the level of competition further.

2. Recruit quality replacements.

To replace the two departing members and add two new ones, I wanted to bring in some combination of RotoBaller colleagues and Reddit users from r/fantasybaseball. This being my home league, I didn’t want to alienate my friends who had been playing for years by turning it into the functional equivalent of an industry league. I’d just be running into the whole ship of Theseus thing after they all quit, which is precisely what I was looking to avoid here. I just wanted some new blood that would put up a good fight.

3. Tweak the rules, if necessary.

The keeper system had been designed to prevent exactly the sort of run I was on, and so it had clearly failed and some sort of adjustment was in order. A few ideas were floated: Increasing keeper inflation by a dollar or two per year, limiting the number of players a team could keep, and lowering the amount of money a team could spend on keepers. I opted to implement the latter, cutting the keeper cap from $180 to $150. This would strike a blow to my roster without hurting most of the other teams in the league.

We also had two expansion teams, and they deserved to not be thrown into a situation where 10 other people had a head start. Enter the expansion draft, which I weighted so that every team that hadn’t finished in the top three could lose only one player, second and third could only lose two, and I would lose four. Both new owners would therefore end up with seven players. Every incumbent owner would be able to protect eight players on their roster.

4. Introduce (or increase) an entry fee.

I received no pushback from any of the other owners when I brought it up again in preseason and it made the math easier for payouts, so I bumped the league dues from $20 to $25. A modest increase, but between that and the expansion, the prize money for both first and second place had nearly doubled as a result.

While instituting an entry fee or raising an extant one may chase an owner away, it’s possible – perhaps even likely – that this departure would qualify under item 1 of this list. Sweetening the pot or putting more than simple bragging rights on the line can also help increase owner engagement.

Bottom Line

Did being both the commissioner of the league and the owner of the team that had broken it put me in an awkward position? It sure did, particularly with that dues increase. But it can be a tough needle to thread even if you’re just the commissioner. The other owner could get upset if he feels you’re punishing him too heavily for success. And as we all know, even just one person getting mad has the potential to throw the entire league into drama and chaos.

I hadn’t cheated. No one was threatening to quit or really even complaining. The league simply needed to evolve to get out of a competitive rut, and doing that required that I handicap myself. At the same time, I didn’t want to scorch the earth, either for my own roster or the league as a whole; the only suggestion that came up in conversation that I immediately shot down was putting every player back in the draft pool and starting from scratch.

So what happened, you may be (but are probably not) asking? Did these changes work? Did any of it matter? Does anything matter?

Well…

Again, though, luck played a role. One of the four players I lost in the expansion draft was Starling Marte, who ended up missing half the year with a PED suspension. Another was David Dahl, who missed the entire season. I gambled and won on a few trades that could easily have backfired, and I made it through the season relatively unscathed by injuries. I also spent most of the season in second place, only taking the lead for good in September.

Should I have made things harder on myself? It’s an argument you could make. But my leaguemates seemed happy with the way I handled the situation and that was all I really cared about. That, and making the game more fun for as many people as possible.

I look forward to going for my eighth consecutive win, and hopefully providing good enough advice in this space to help you start or maintain a streak of your own.

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