Playoff Strategy: Reacquainting Myself with H2H Leagues

A year or two before ottoneu was founded (so about a decade ago) I swore off head-to-head baseball leagues. The beauty of baseball, I think, is in the daily grind – six months of daily grind, with no one day being more important than any other. Besides, if you are going to make one day count more than another, choosing September, when the rules of the game change and when different teams have such wildly different incentives and goals just does not make sense to me.

But I am now in my second year playing in a matchup league again. I took over a last place team in this dynasty league, barely missed the post-season a year ago, and now I am just a few hours away from my first playoff matchup in years. And the strategy for the post-season is taking some getting used to.

By far the most frustrating thing for me has been the injury/DL situation. This league allows four bench slots and three DL slots, which should be more than enough room for any team, but September creates issues. In the last two weeks, I have seen Ike Davis and Justin Masterson go down with injuries that, under normal circumstances, would mean DL stints, allowing me to stash and replace them. Instead, with infinite roster space, the Mets and Indians chose not to DL either of them, forcing me to cut Davis and to waste an active roster spot on Masterson, who is too cheap to cut and risk losing.

The problem of course is that in the fantasy playoffs, missing a single start can be devastating. You lose something like 10% of your pitching stats. If you are in a roto league and sitting on Masterson, losing a start or two, or even three or four, is frustrating but just a blip on the radar over the season. In a one week matchup with the season on the line, one start can be a back-breaker.

I am dealing with a similar issue with Carlos Gonzalez, who would never be on the 25 man roster as a pure pinch runner/defender, but is no longer on the DL despite having zero fantasy value. Do I drop CarGo, effectively handing a dirt cheap keeper to whoever picks him up, or waste an active roster spot on him, too?

All of which gets me back to the real question at hand – how does strategy change when playoffs come into the picture?

I am a big believer in the idea that flags fly forever, and in my roto leagues, I tend to be an aggressive buyer when I think I have a shot to win the whole thing. But a third or fourth place finish is not worth sacrificing the future. The problem is the playoffs make it so much harder to know where you stand. Yes, there is the simple in-or-out question, but beyond that, it is up in the air. I am going to finish the regular season in fourth, but as late as the middle of this week, I was sitting in second. So what does that mean? Should I be aggressive (screw Gonzalez and Masterson, I need guys who can help me win NOW!) or is it not worth selling off keepers when I am a bad day away from the 5th/6th place finish that comes with an early playoff exit.

In general, my advice would be to stay aggressive, but not crazy. For me, that means letting go of Avisail Garcia, a player whose future I think is very bright, because he is likely to miss about half this week with a tooth issue (yes, a tooth issue). It means passing on Cody Asche to pick up Alex Rodriguez who I imagine will have no value next year, but seems like a valuable addition for the stretch run this year. It may mean dropping Danny Salazar, who may be electric but who also isn’t getting enough innings to qualify for wins.

It does not, however, mean dropping a top tier OF and potential MVP candidate (pre-finger injury) nor does it mean dropping a SP with a top-75 ranking and a $3 salary.

How do I plan to float two useless roster slots? First, I am picking up a two-start SP for this week (giving me three total). My first choice is Zach McAllister, but Mark Buehrle is on my radar, as well. Second, I am going to be willing to turnover the rest of my roster to pick up a game played here or a game started there.

And third, I am going to remind myself that the playoffs in fantasy, just like in real life, are more game of dice than game of baseball, and that anything can happen. I think the moves above will help line me up for a shot at a title, but a little luck (get back in the batter’s box soon, CarGo!) wouldn’t hurt.

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Chad Young is a product manager at Amazon by day and a baseball writer (RotoGraphs, Let's Go Tribe), sports fan and digital enthusiast at all times. Follow him on Twitter @chadyoung.

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i like the h2h playoff strategy in that it brings some of the frustration and unpredictability of real baseball into fantasy, but it definitely has some issues. in a 16 team dynasty league i’m in, our playoffs started 2 weeks ago so this week is the final week. This is actually a little better than waiting til the final weeks of the reg season, as it means mlb teams haven’t completely given up and are still trying to field competitive teams. I’ve seen some leagues that make the playoff matchups 2 weeks, which is also a good way to make up for the vagaries of sept baseball.

my strategy was essentially to build a team ready for the playoffs. in my league this meant pitching depth, and not caring about whether i won or lost any given week in the regular season as long as i was in competition for a playoff spot. last year i went into the playoffs as the best team in the league, but lost in week 1 because i was forced to pick up bruce chen as the best available 2 start starter. This year, i was prepared with enough depth that the only reason i lost is cuz Kershaw was slightly less than amazing and put up 0 points for me in his 1st start of the week. That kind of thing happens, hard for me to be mad as i had done the best i could.

i think h2h leagues work best if they are very deep or very shallow, making it easier to make keep or cut decisions. if you can have 3-5 keepers, then deciding what to do with danny salazar or ike davis becomes a lot easier. if you have a deep bench, then you may be keeping everyone anyway.

the other thing with h2h is, if there’s a trade deadline, you basically have to get your roster down to guys you’ll either definitely keep or definitely cut by that deadline. if you get riddled with injuries to keepers heading into playoffs, thems the breaks and your year might be done. it’s much harder to justify cutting decent keepers in favor of help today given the variability associated with h2h playoffs.