All-Star Break Rest-of-Season Strategy: Head-to-Head Leagues

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Happy All-Star Break to all you fantasy baseball nerds out there. As we sit through what seems like the longest four days of the summer, I thought it might be helpful to discuss some general season-long strategy for the rest of the year. Of course, strategy can differ greatly based on your league type, so I'll be supplying some thoughts for both rotisserie and head-to-head leagues.

In head-to-head leagues, the goal is to find a way into the playoffs while also preparing for them. I'm going to assume we are working with a weekly matchup, redraft format in which points are accrued weekly, walks and HBPs help batters, and strikeouts hinder them. At the end of the week, you get a win, loss, or tie for that week, and a certain number of teams make the playoffs. This format is much like the majority of fantasy football formats. With that in mind, it's much more likely that a middle-of-the road team  can find it's way to the championship than in a roto league (which I've discussed in depth in a previous article). Likewise, it's very possible that the best team in the regular season can lose in the first week of the playoffs. While this nerve-racking amount of parody and varience disturbs me, there are plenty of fantasy baseball players who enjoy it.

So, let's look at three different, general scenarios that you may be in right now in your head-to-head league and talk about how you might effectively go about making the playoffs and continuing your success through to the championship matchup. If you have specific questions or you want to chat more strategy, I'm always open. You can find me on Twitter @BellRoto. Best of luck to you in the home stretch!

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H2H League Strategy Rest-Of-Season

Top 33% - Two Games or Less Out of First Place

The variations of head-to-head leagues that exist make specifics very difficult in this type of article, but there are a few main foundations that need to be taken into account at this point in the year if you'd like to have success in these next few months. First, the playoffs allow for more owners to be in the running for money and the championship. Thus, as long as owners don't give up on their teams, there should be more competition for a longer period of time than in roto leagues. Second, the fact that the playoffs exist means there is a shorter regular season. This means that h2h leagues are likely close to 65% or 70% over by now instead of roto's 55% or so. Lastly, the fact that you're matching up against one player each week provides variance in that you could both go on a huge run, winning five or six weeks in a row against poor opponents, or go on a cold streak, playing the top point-scorer three times in a row and losing mulitple weeks despite your team performing well compared to the league as a whole.

This is why I no longer play head-to-head fantasy baseball, and it's also why I would jump at the chance to play in a sensible roto-type fantasy football league. Even still, there is plenty of strategy that goes into h2h leagues, allowing for us to analyze such strategy for the rest of the year.

Let's assume, for simplicity's sake, that you're in a 12-team head-to-head points league (no divisions) that has six playoff spots. This category, then, would likely identify the top four teams in the league at the All-Star Break. These teams are likely going to make the playoffs by season's end, so their main concerns right now are getting as high as possible in the standings, but also preparing for the (likely) three weeks of playoffs. In this case, the top two teams would likely receive a first-round bye. That concept can also bring in a whole different bundle of strategy.

Aside from picking up high-upside waiver fodder to fill your bench, DL, and NA spots, you should also be looking to handcuff important pieces of your team if you're in this position. An example of this, similar to picking up the back-up running back in fantasy football, is stashing the set-up man for your closer. This move makes more sense in some scenarios than others (possible trade, closer struggling, set-up man really good numbers, etc.), but it should be mentioned regardless. If there is not an opportunity to handcuff one of your closers, perhaps picking up a speculative, future save-getter like Archie Bradley would be a good move.

Another non-trade piece of advice that makes sense for a team like this is fine-tuning strategy and studying opponents. Depending on the restrictions in your league, you may be able to successfully deploy a zero-RP or zero-SP approach, altering the types of players you start each week dramatically. Perhaps you're beginning to notice that speedy, stolen base threats constantly have better weeks than streaky home run hitters. Now is a good type to explore those strategies to ensure you aren't leaving points on your bench or on the waiver wire. If you can begin to guess who your first playoff game will be against, you can try to undermine their strategy as well. The list goes on in terms of mini-strategies that you can use to incrementally better your winning chances once the meaningful matchups begin.

Lastly, trading is an obvious method of improving your team, and you can amplify the waiver wire strategy above by trading risky players for predictably reliable players that better compliment the foundation of your team. You can also begin to look ahead to the playoff weeks and cater trades for those matchups specifically. This works great for starting pitchers, as you might be able to trade Jon Gray at home against the Diamondbacks for Sonny Gray at home against the Angels.

I could go on for hours on how to prepare for the playoffs, and still it might not be relevant for your specific combination of rules and regulations. My point with this section is simply that you should begin looking forward to the playoff weeks as soon as you can without hindering your chanecs at a good regular season finish. Variance and parody makes things very interesting in head-to-head points leagues that include playoffs, so preparing for those weeks when your opponents are just trying to make the playoffs can give you a slight advantage.

 

Middle 33% - Between Three and Five Games Out

It's go time, folks.

If you're in this category (likely between sixth and eighth in the specific league we outlined above), you can't afford to wait any longer for regression to come. Perhaps the player who's still barely making the playoffs can wait-and-see for another week or two. But remember that playoffs cut down the regular season tremendously, and you would rather not have to "win-or-go-home" in the final week of the season if you can avoid it.

Fantasy owners in this category should be seeking out possible consolidation trades in order to buy stud players that can help you big time on a weekly basis. You should be able to find some solid replacement value on the waive wire, and hopefully the move you made to get Manny Machado in Week 16 pays off in the first round of the playoffs in the form of five home runs and 12 RBI. Don't be afraid to be risky here, either. The owners in the section above might be looking to get rid of what we thought were slow starters because they would prefer a safer bat in the playoffs. Rougned Odor, Nick Castellanos, and Yoenis Cespedes are three relatively risky hitters that I could realistically see hitting 20 home runs between now and the time your playoffs start. If they don't, you might miss the playoffs by one game. But if they do, you might be looking at a first-round upset on your way to a big payout.

Streaming should become more prevalent for fantasy owners in this category as well, as you can no longer afford to trot out John Lackey with the hope that the Cubs score enough runs to at least get you a win. Choosing hot, lesser-known hitters with good matchups over veterans who might sit out a game can be a viable strategy to steal a few extra points as well. Whatever you can do, risky or not, to potentially steal you a win each week should be considered. You are not at the all-or-nothing stage yet, especially in the leagues that send a lot of teams to the playoffs, but you're not sitting pretty either. Buck up and make some moves if you still want a legitimate chance at winning this league.

There's not nearly as much to say about these teams because the path they should be taking is pretty clear at this point. Good luck to those of you in playoff-limbo right now, and please don't be the guy who misses the playoffs by one game because he refused to trade (or drop) the fading player on his favorite team.

 

Bottom 33% - More Than Five Games Out

While I still will promo RotoBaller's great fantasy football content that is already pouring onto our great website, there might still be time for these folks in head-to-head fantasy baseball leagues. Depending on the playoff size in your league, a nice winning streak could put you right in the thick of things. On the other hand, if you're seven games out of a playoff spot with seven games left, you can probably rip the band-aid off now and hit that "Football" tab up top.

With that being said, and this is even more important here than it was in the roto write-up, please do not completely forget about your team now that you're mathematically eliminated from playoff contention. With weekly matchups determining playoff status each week, you need to at least check-in every Sunday to make sure there aren't any injured players on your roster and that the best players on your team are starting. If you don't want to touch waivers or field trade offers, fine. But don't ruin everyone else's fun by giving the sixth place team a free win in the second-to-last week.

For those cellar dwellars that still do have a chance at a playoff spot, you better hit your league's group chat platform now and start talking some trades. Make some risks, buy some players that nobody wants, and pretend like every week is a must-win week... Because it pretty much is. I shouldn't have to tell you much more than that. The majority of fantasy advice on podcasts and in articles will be catered towards the owners in the two sections above, but you don't have to be reasonable anymore. If you think Luis Castillo and Joey Gallo could explode the next two months, go trade Jake Arrieta and Jonathan Lucroy for them. You can't afford to wait on those guys at this point. YOU NEED TO WIN NOW!

You get the gist. Rankings or buy-low/sell-high trade advice won't help you now. Go with your guy and try to make a movie-worthy miracle happen in the next handful of weeks. Good luck, soldier.

 

Conclusion

Again, hit me up on Twitter with any questions or comments you may have (@BellRoto). I love talking strategy about fantasy baseball.

For those of you looking for roto strategy advice, there should be an article posted nearby with a very similar title but a very different body. I wish you all the best of luck, except of course my fellow writers and editors here at RotoBaller with whom I share a very important set of standings.