Crafting your Fantasy Baseball Portfolio

We have probably all faced this dilemma at one point or another during our fantasy baseball playing days. A friend of yours sends you an email saying he has an opening in this great league and wanted to see if you were interested. You hardly take a look at the league settings before you decide that you will join up. Then the problems start.

  • You have never played in a league with these quirky scoring settings. I mean, +5 for a game winning RBI, -2 for a double allowed. What?
  • The grind of a league with daily roster changes is too much work. You forgot to set your lineup and Yu Darvish threw a no-hitter with 14 K’s.
  • Who are all of these prospects that these guys own? You can’t even tell me who the starting LF on your favorite team is let alone who the starting LF for their AA team is.
  • The team you took over is terrible. Let’s face it, most owners of championship teams are not stepping aside anytime soon. Time to rebuild.
  • You have not had time to shave in 3 weeks and your wife is starting to complain about the Duck Dynasty beard you are sporting. Maybe these leagues are taking up too much of your time.
  • Your best pick up line is a story about waking up at 2AM to scour the waiver wire, adding Hisashi Iwakuma before anyone else.

One of the great features of fantasy baseball is that there is almost an infinite variety to the leagues you can play in. While I am well past the days of signing up for as many leagues as I wanted, I still play in a wide variety of leagues. Currently I play in 5 leagues, but I would like to add one more league this year. Having a balanced portfolio of league styles allows me to stay interested in all of my leagues while reducing some of the offseason and in season work I need to do to stay competitive. Let’s take a look at some of the different types of leagues you can play in and then see how you can build your fantasy baseball portfolio.

Rotisserie Leagues

The purest of fantasy baseball leagues, the style that started it all. If you have not watched the ESPN 30-for-30 film, Silly Little Game about fantasy sports, be sure to check it out.  Rotisserie relies on quite simply counting statistics. Categories for hitters and pitchers are selected, with the most popular being a 5×5 setup (R, HR, RBI, AVE, SB for hitters and W, SV, K, ERA and WHIP for pitchers). You can also customize the settings any way you want, making a 6×6, 10×10, 7×12 league. The rotisserie league I play in is a 12-team 5×5 league. It also has the twist of being a keeper league (more on that later).

Head-to-Head Category League

These leagues are sort of a twist on the rotisserie style. Each week you play against another team, competing across a number of categories. Again, the settings would be similar to rotisserie with categories for hitters and pitchers. The team that wins the most categories wins the matchup. You can also assign victory based on the number of categories, so you could go 3-7 one week and 7-3 the next instead of 1-1 over those 2 weeks. I have played in several of these leagues in the past. The leagues I played in usually had a minimum number of innings you had to pitch as well in order for your pitching stats to count.

Head-to-Head Points League

This is the most common league style I play in these days. The scoring settings can vary tremendously, but essentially, a point value is assigned to everything from a walk to a homer to a game-winning hit to a strikeout, a win, a blown save. At the end of the week the team with the most points wins the match-up. Points are tracked all season and generally wildcard playoff teams are assigned based on total points scored over the course of the season. This is a great way to keep wildcard teams interested in the league throughout the entire season.

Keeper versus Non-keeper

When I first started playing fantasy baseball all of my leagues were single year leagues, or redraft leagues. One thing that was great about this was that if you had a bad year, no need to worry, you would redraft a brand new roster the next year. Of course, if you happened to find a great rookie late in the draft, he was thrown back into the draft pool the next year with everyone else. Now all of my leagues have some keeper aspect to them, and these are as unique as the leagues themselves. One league allows us to keep 8 players, no year limits, no salary cap. Another allows us to keep 5 players, but we can only keep a player for 3 years. Others have salary caps based on points scored. Another version of the keeper league is a dynasty league.


If you really want to feel like a GM, then a dynasty league is probably for you. After the initial draft, you own your roster for as long as the league exists. Some dynasty leagues add in salaries, so you have to decide how long to sign players for. Often there are restrictions to contact lengths. These leagues sometimes include minor league rosters with special contract rules for promoted minor leaguers.

Minor League Rosters

As if tracking the who’s who of MLB rosters is not complicated enough, now leagues are offering the ability to maintain a minor league roster. Sizes of these rosters will vary across leagues. I have one league where we have 4 minor league slots, and others where we have 13. You can imagine in a 12-team league with 13 minor league slots that the work to know which prospects to target can be daunting (of course you can get all the prospect information you need from us here). Of course it can also be a lot of fun and really rewarding when a minor league player comes up and develops into a superstar.

A quick side story of one of my most successful trades: as a co-GM for a team in a keeper league with 4 minor league slots, I successfully obtained Milwaukee Brewer prospect Ryan Braun 1 day before he was called up to the majors. In case you forget what Braun did when he was called up, he simply hit 34 HR, scored 91 runs, drove in 97 runs, stole 15 bases and batted 0.324 in 113 games in 2007.

AL and NL-Only Leagues

These leagues can fall under any of the above categories, but your roster is filled with players for only one league. While the player pool is greatly reduced in these leagues, the complexity is not. I would like to add one of these leagues to my portfolio this year as I have never played in one.

Salary Cap or No Salary Cap

I mentioned salary cap as a way to determine keepers and in dynasty leagues, but there is more to a cap than simply determining your keepers. In some leagues you have to assign contracts to players. Sometimes player values are created by outside sources and players can be signed to multiple year contracts with increasing annual values. Salary caps also fit very well in the next league style, Auction Leagues.

Auction League

I had never done an auction draft until last year, and now I want to add a few more in. I actually switched my long running football league over to an auction league a few years ago and owners really like it. I mean, how many times have you showed up for the draft to find that you are sitting in position 11? You know off the bat that you are not going to get the chance to own your favorite player, Mike Trout. Change your league to an auction league and the highest bidder can own whomever they want. No more feeling defeated when your buddy selects the next guy in your queue 2 picks before you, 3 times in one draft! An added benefit of the auction draft, everyone is paying attention to every pick because everyone has a chance to get that player. It makes for a more active draft, more draft room trash talking and definitely adds a lot of unique strategies.

Weekly Leagues versus Daily Leagues

I am not talking about the recent craze of sites like but rather how you elect to set your lineups. Obviously daily roster settings are more time intensive than weekly leagues simply because you have to login each day and make sure you have a lineup set. I mean, you can set your lineup and like Ron Popeil “set it and forget it” but you run the risk of missing out on a great performance from someone on your bench. Weekly leagues require some forethought. Do you start the #3 starter with 2 starts this week, or the #2 guy who has one start, but against the worst team in the league? Do you sit your stub OF because he may miss a game or 2 this week due to a hamstring injury?

OK, now that you have an overview of some of the types of leagues you can play in, how do you build a fantasy baseball portfolio? Building the portfolio is a lot like building your investment portfolio. You want to hedge your bets a little bit. You don’t want to play in only Dynasty Salary Cap Leagues because you could get stuck in years of misery if your teams under-perform. You may not want to play in 10 redraft leagues because you have to find the time to run 10 full drafts every year. Balance is good, and allows you to try out different league styles. Here is how my current portfolio looks.

  • Total fantasy baseball investment: 5 leagues
  • Weekly versus Daily breakdown: 4 weekly, 1 daily
  • Keeper: all 5 leagues have an aspect of keeper to them
  • Minors: 3 leagues have minor league systems
  • Head-to-Head points: 4 leagues
  • Rotisserie: 1 league
  • Dynasty: 1 league
  • Salary Cap: 2 leagues have salary caps League sizes: range from 10-team to 14-team

Heading into draft season, I know that I will have to prepare to draft players in all of my leagues. However, a couple of leagues are setup to offline drafts utilizing the league message board. Each team is allotted 12 hours to make their selection, so there is not the commitment of showing up the Draft Room at a given day and time. I do have 3 leagues that draft online. In the past I have run into situations where I have drafts on 3 consecutive nights, or even multiple drafts on one night. Because all of my leagues are keeper leagues, I already have an idea of how my roster is shaped heading into the draft, so I save some time in draft preparation there. Due to the points-heavy portfolio I have, I can run a similar strategy in my drafts. I do spend a good amount of time creating projections for players to help craft my rotisserie strategy. And the amount of time I put into researching minor league players pays off because I have minor league systems in 3 leagues.

For 2014 I would like to add one league, an AL or NL-Only league. Not sure what style of league I want to do yet, but I think I will stick to a redraft format for year one. This will allow me to see if I like the one league style, and then I can try the other league next year. Draft dates are starting to be finalized, so once I know when I have time in my schedule to sit down for a 2 hour draft, I will get signed up. Now which site to play at? Stay tuned.

11 thoughts on “Crafting your Fantasy Baseball Portfolio”

  1. Hi Matt, interesting question. For this particular league I take some time to look at what category totals were needed to win each year. Then I project my keepers totals and tailor my draft to try to reach those numbers. I usually view SP with less value because I feel you can simply accumulate stats by getting to the inning cap (Always pitch to the cap). This year I have to change that strategy a bit because I am keeping Darvish and Jose Fernandez among my 5 keepers.

  2. I’m looking for a good rankings/projections list for my H2h points league draft…any suggestions? Thanks, J

    1. Check out our consolidated rankings, and definitely stay tuned as more lists are being developed. Of course feel free to drop us specific questions in the Ask the Assembly section. Thanks for checking us out

    1. J, I agree with Pete’s basic strategy for points. One HR generally nets you 6 points: 1 for the run, four for the HR, and at least 1 for RBI. If a player gets a single/walk and a SB, that’s usually just 3 points. Power goes a lot farther than most speedsters in points leagues.

      That being said, the type of profile of the batter doesn’t matter in the end, because everything is converted into one comparable stat: Points. If a player like Bourn at his peak, and even Ellsbury (minus his one power surge year) can consistently net good points, it doesn’t really matter how they get them. It’s just that speed is more risky than power.

  3. Hey J
    I do have a basic strategy that I follow for H2H point leagues. I focus on power hitters early in the draft. Generally HR are worth more than steals, and good power hitters will deliver runs, RBIs and doubles, which offer solid scoring opps. I also make sure I add power hitters in the positions where I need to have power (CI, 2 OF slots, and if I can add power at 2B/SS I do that). I am willing to reach a round early to grab elite power guys too. I don’t draft a pitcher until at least round 7 (caveat being if a guy like Cliff Lee is there in the 6th round he is too good of a deal to pass). For SP I focus on guys with high K/9 and don’t go chasing wins. I try to grab 1 solid RP (like a Greg Holland, Aroldis Chapman-type), and then grab elite setup guys again with high K/9 to fill out my bullpen. My bench is generally mostly pitchers (for streaming as well as getting more bang for your buck with upside guys: see Jose Fernandez 2013) and a sleeper hitter or 2.

  4. Peter, in a h2h points league draft, of your first 10 picks, how many are hitters & how many are pitchers. Are there certain positions you wanna make sure you draft in first 10 rounds? Thanks, J

    1. Thanks for the question J. Pete has gone away for a few days so I thought I should jump in in case you need a quicker response. I’m sure Pete will give his feedback upon his return 🙂
      In the first 10 rounds, you’re going to need your corners, at least one outfielder and likely 2-3 pitchers. So that’s 5 or 6. I wouldn’t plan it this way…just keep in mind that when the opportunity comes where there’s good value at those positions to grab it.
      As much as all of the planning is crucial to your draft success, you really need to be able to adjust as the unexpected will surely happen. So don’t plan for positions, but recognize that if you don’t have your corners by round 10, you’ll be in some trouble. Outfield is not very deep either depending on your league set up. If it’s 12 teams with 3 OF, it’s not SO critical but if it’s 4 OF then you can’t wait too long or it’ll be hard to recover.
      In a perfect scenario, you’ll have your infield, 2 outfield and 3 pitchers but again, the values you get in each round is the important thing. Good luck, I’m sure Pete will give his feedback and likely have some other ideas as well for you.
      Thanks for reading.

      1. Last year in my roto league, I locked up hitting with 8 of my first 10 picks, but in rounds 5 and 6 I grabbed Kimbrel and Chapman. I like to lock up first and third with a stud/high caliber player along with a big bat to back up one of those positions for my utility/CI slot. Second or short are a priority. I’m not going to reach just to fill both, but I will get at least one top 5 at one of those positions and try and fill the other one in rounds 7-10. The other slots are OF. My first starting pitcher wasn’t taken until round 11, but I don’t recommend that unless you’re good at finding hidden treasure last in the draft or on waivers during the course of the year.

      2. Paul, thanks for the advice! What type of players are you targeting toward the end of your draft…certain positions or upside players? thanks, J

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