Head-to-Head: Unorthodox strategies

I haven’t talked at all about head-to-head leagues here, mostly because I’m not a fan of them. I dislike the concept of fantasy playoffs and how one poor/unlucky week can cost you an otherwise fantastic season. I’ve gotten a few questions about them, though, and there’s been some good discourse about head-to-head leagues over at the Fantasy Baseball Generals, so I decided to put a few of my own thoughts out there.


At FBG and on his radio show, Patrick DiCaprio has talked about the importance of analyzing potential matchups in head-to-head leagues. It isn’t enough to simply throw together any mishmash of players and go into battle against a differently constructed team each week. You need to analyze your competition a bit and decide how they will construct their rosters. You should then build yours to capitalize on the weaknesses of your opponents.

Common strategies

Patrick identifies two strategies that players tend to follow in “garden variety leagues.” One he titles the “standard strategy” and another the “pitching strategy.” The standard strategy is where the owner essentially ignores pitching for the first several rounds and takes hitters. The pitching strategy is where the owner tries to capitalize on all the people using the standard strategy and take pitchers early.

Punting categories

One thing that I think is a huge factor in determining a head-to-head strategy is the fact that categories can be punted. In fact, thinking about it just a little bit over the past few days, it seems to me that it can actually be a good strategy to punt certain categories.

In a competitive 12-team rotisserie leagues, it can be very difficult to win if you punt a category. In these leagues, being third worst in home runs still gets you three points and contributes something to your goal of winning the league. In a head-to-head league, being third worst in home runs doesn’t mean nearly as much. If your team is that poor in home runs, you’re not going to match up very well with other teams in that category and you won’t get much benefit out of having the third worst collection of power hitters.

Your resources would be better used punting those spare home runs and allocating the resources to a category you are stronger in. Then, you can pretty much assure yourself of a win in that category every week, as opposed to hoping for one win in home runs once every month or two.

Suppose you’re ninth in steals. Get rid of those homers and add more steals. If you can absolutely dominate a category, you can pretty much bank on winning that category every single week. There will be some fluke weeks, but those can happen to anyone using any strategy.

The fact that you can punt categories and get away with it lends more support to pursuing the pitching strategy. You are going against the grain and potentially earning an advantage for that simple reason, and it is easier to punt a hitting category than a pitching category. By taking pitchers early, you will more easily dominate a larger number of categories. If you draft a good starting pitcher early, he will perform exceptionally in four categories. Not all top hitters will do that.

By taking pitchers early, you will be rocking four categories right off the bat. Throw some closers in there and you’ve got all five. And in leagues where you decide your competition is likely to wait on pitching with few to no teams pursuing the pitching strategy, you will have an advantage over all of them if you take pitchers early and have good judgment on which to select. Then you just need to win a couple of offensive categories and you’re set… which leads into a strategy that I would like to try one day.

My potential strategy

This strategy is a variation of the “pitching strategy.” Taking it a step further, I would tailor my offense in a very specific way. Using the pitching strategy, you’re not going to have many resources to use on hitting and might be tempted to spread your offense somewhat thin in an attempt to compete in several categories. As I said earlier, though, it doesn’t make much sense to be only mediocre in a category. You don’t have to compete in every category in head-to-head leagues; you need to be great in just more than half.

Therefore, I would try to dominate two or three offensive categories and punt the other two. For example, it would be possible to employ the pitching strategy and still be able to dominate steals and batting average and be in the top tier in runs. You will resign yourself to losing home runs and RBIs every week, but if you can take four of the pitching categories and two of the remaining three hitting categories, you’ll win every week and have some room for error.

In a nutshell, here are the player qualifications I would shoot for (combining 3, 4, and 5 whenever possible and placing the least emphasis on 5):

1. Good starting pitchers on good teams
2. Highly skilled closers regardless of team quality
3. Players who steal a lot of bases
4. Players who have good batting average skills
5. Players who hit early in their team’s batting order

Here are specific players I might go into the draft hoping for. Realize that in a real league, I would have multiple contingency plans to account for guys being taken earlier, but this should give you an idea about the types of players I would target.

Round 1: Johan Santana
Round 2: Carl Crawford/Ichiro Suzuki
Round 3: Bobby Abreu
Round 4: C.C. Sabathia
Round 5: J.J. Putz
Round 6: Chone Figgins
Round 7: John Smoltz
Round 8: Jose Valverde
Round 9: Juan Pierre
Round 10: James Shields
Round 11: Rafael Soriano
Round 12: Yovani Gallardo
Round 13: Michael Bourn
Round 14: Willy Taveras
Round 15: Joakim Soria
Round 16: Aaron Hill
Round 17: Casey Kotchman
Round 18: Scott Hatteberg
Round 19: Paul Lo Duca
Round 20: Jeff Keppinger
Round 21: David Eckstein
Round 22: Luis Castillo
Round 23: Josh Bard

This, I think, would be a team capable of winning seven or eight categories each week. It would always lose in HRs and RBIs, but it would have plenty of steals and an excellent batting average. Plus, there are a number of fast guys, leadoff men, and No. 2 hitters to score runs.

Mental Health and the CBA
A particular bit of language in the latest CBA could have negative consequences for some players.

As a side note, if the league didn’t have a minimum at-bat limit and/or allowed certain positions to go unfilled, I’d consider trotting out a less-than-full team if my draft didn’t go exactly as a planned. For example, most catchers don’t steal bases or hit for a high average, contributing mostly in home runs and RBIs. Since this doesn’t jibe with my strategy, I might just leave that catcher spot empty if I wasn’t able to get one to contribute in batting average.

This strategy and match-ups

This team, I believe, would match up very well with teams employing either the traditional strategy or teams employing the pitching strategy that don’t punt categories. It would also do well against teams that have a mishmash of hitters and pitchers.

Since there are relatively few stolen base threats available in a draft, it would be difficult for a team to match up with me in that area unless it conceded several categories as I did. It would become nearly impossible for others to match up when you consider how many of the top stolen base guys my team would take off the market.

Few teams would match up in batting average because most owners don’t try to win only a couple of offensive categories, as I would do. Instead, they take power hitters who—even if they all can hit .280-.285—can’t match up with my guys, who should all hit above .285 (sans Bourn).

Some teams could be competitive in runs, but I’m only shooting for them out of circumstance: Many stolen base guys hit atop the order, and their speed helps them score runs. As an added benefit, because I’m also looking for high-batting average guys, all they’ll need is a decent walk rate to get on base enough to score runs for me. I don’t actually need to win runs, ever, if I win four pitching categories plus batting average and steals. Being competitive in runs simply gives my team an additional “out” should I have an unlucky week.

Then all I need to do is draft the right pitchers and hope not to get unlucky. I have the advantage out of the gate because I’ll have several top pitchers, a luxury most teams won’t have and which will make them unable to compete with me in the pitching categories. As long as I trust my judgment with pitchers, this is a strategy worth pursuing.

I realize that I could finish in the bottom half of the league if several of my pitchers get unlucky. Using the probabilistic concept of value, though, this possibility is built into the pitchers’ projections and in the long run this strategy will work out well.

If we think about it ultra-simplistically, when I run into good luck I’ll do well. When I run into neutral luck I’ll do well. Only when I run into bad luck will I fail.

This seems, to me, like a much better plan than to simply go with one that everyone else is going with. If I do that, I will do well only when I run into good luck. When I run into neutral luck, it will be a crap shoot since I’ll be using the same strategy as others, and if enough others are using it the chances of someone else encountering good luck increases, which would trump my neutral luck. I would also, obviously, do poorly when I run into bad luck.

Potential pitfalls and adjustments

Against tough competition, this plan might be difficult to carry out.

In competitive leagues, you’ll often find people following the traditional strategy, making the pitching strategy all the more powerful. Even so, they’re still top competition and will probably be tracking what you’re doing, especially if you have a reputation. When they see you taking steals and batting average guys, they might try to thwart your strategy.

This is something to be aware of, and if you have a feeling someone has caught on, you might need to take some of the more important guys a couple of rounds earlier to make sure you get them. Willy Taveras, for example, is a pretty important guy in this plan. After him, there aren’t a lot of guys who will steal 30+ bases and hit .290+. Taking him in Round 12 (or earlier) wouldn’t be the worst idea in the world.

Taking Juan Pierre in Round 7 and a guy like Felix Hernandez or Daisuke Matsuzaka in Round 9 (instead of Smoltz in Round 7) might be a good idea too, if you think taking Ichiro, Abreu and Figgins has people wondering. Pierre isn’t critical to the plan given the potential for playing time loss in LA, but even if he gets 30 steals this adjustment might be worth making. Judgment call.

In preparation for your late-round batting average push, it might be worth it to use a couple of picks in the teens on some power hitters who are generally considered sleepers, just to throw people off. By pick 13 or 14, it would probably only look like you’re going for steals (not necessarily batting average). After taking Soria, going with two straight power hitters might make some owners think that you are simply trying a strategy where you take speed early and power late. If they decide to combat this, they’ll start taking power hitters… perfectly fine with you. If they don’t try to combat this, it makes no difference at all.

By taking two power hitters and then shifting to your batting average targets, the earliest I could see someone catching on to what you’re really doing is in Round 20, so you could spend Round 21 on another power hitter. Most of the late round, batting average guys you’d be targeting would go undrafted anyway because they don’t contribute much in the other categories, so after the draft it would only take a few minutes to make some add/drops and fix up your roster.

By strategically selecting the power hitters, it should throw all but the most perceptive opponents off the track.

Even riskier, you could fake your way through the entire end-game. Most of the guys on the list aren’t getting drafted at all, and ignoring them completely would make your plan 100 pedrcent imperceptible. Take power hitters with a couple of your real targets sprinkled in (or none at all for maximum boldness), and then after the draft pick them all up. Just make sure no one else looks like they’re using a similar strategy; then those hitters might not be there for you after the draft.

Concluding thoughts

Next on the agenda is a post about Double-A pitchers to watch and another with some thoughts about auctions. Be sure to look for those in the coming days.

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