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Winning Strategies for Drafting a Fantasy Baseball Team

By Edited Jun 9, 2015 1 1
Winning Strategies for Drafting a Fantasy Baseball Team
Credit: mjpyro

I have been playing fantasy baseball in Yahoo since 2001. Eventually I started my own league, and I am starting my eleventh year with a team.

Each year in early spring, I schedule the draft for around the end of March so that all managers have a better idea of who is going to be starters and more importantly, if any significant injuries were suffered in spring training.

This year I ended up with the 5th pick, which I consider “no man’s land”. With that pick, I did something that I have never done. I drafted a starting pitcher, Clayton Kershaw. He was so dominant last year that I figured he was the best bet given that the superstar hitters like Miguel Cabrera and Mike Trout were already gone.

Unfortunately, the Dodgers had a game in Australia the week before the draft and I didn’t get that dominant start from Kershaw in my stats. Then a week into the season, he went on the disabled list for over a month so I thought I had really messed up.

He came back in the middle of May and has been dominant again except for one start when he blew up for 7 or 8 runs in a few innings. You know how that can destroy your team ERA and WHiP.  In fact, I have an All-Star team for the ages of lefty starters on this year’s team (Kershaw, Hamels and Lee), all of which have spent time on the DL and had at least 1 blow-up start. For the first 2 months of the season, I had the worst team ERA and WHiP in the league if you can believe it, but it is slowly declining.

For years, I did not draft any starting pitchers. I came across an article once about winning a league by only drafting closers which in theory would allow you to dominate several categories including Saves, ERA,  WHiP and Loses category if your league had that stat. You basically conceded the Wins category, but if all worked out as planned according to statistics, you would have maximum points in 3 or 4 of the other categories.

I tried this strategy for about 7 or 8 years. I even added a Holds category to my league so I could use some of the dominant setup men, so that was another relief category I dominated.

The results?

I believe I won the league once using that strategy in about 7 years. It does not work. Everything has to go perfectly for it to be successful.

However, based on my 14 years of drafting fantasy baseball teams, I have come up with several tips for what to do and not to do if you want to compete for the title.

First 2 Rounds of the Draft

What you do in the first two rounds depends on where you landed in the random draft order selection. Most drafts work by going down the line in order, then reversing the order and coming back to the top. So if you have the number one pick, you are going to get the best player in the league, however, you are not going to pick again for a while. If there are 10 teams in your league, you are not going to pick again until the 20th pick in the second round. So you better make that first pick count.

Normally, I prefer to get the third or fourth pick, but this year, I wanted either Cabrera or Trout

Winning Strategies for Drafting a Fantasy Baseball Team
so I was disappointed and took Kershaw because no other hitter stood out. In retrospect, I should have taken Giancarlo Stanton who is having a breakout year with the Marlin. I had him last year, and he somewhat disappointed but that had to do with the Marlin’s weak overall offense. Teams were pitching around him.

So here is what I advise for the first two rounds if you end up with the first, second or third pick in the draft. I will assume a 10 team league to keep the numbers simple.

1st - 3rd pick – take the best overall hitter. Do not be swayed by any starter’s stats no matter how dominant they were in the previous year. A starting pitcher can only help your team once every 5 days, but an everyday position player is out there mashing for your stats every day, affecting potentially 4 to 5 stat categories.

4th – 7th pick – here is where the decision process gets a little harder. By this time, there aren’t any dominant superstar stat hitters left, so you can begin to peek into the dominant starting pitchers as I did with Kershaw. Again, I had never taken a starter pitcher before in the first, second, or even third round.

However, if you select a starting pitcher with your first pick, it is imperative that you go for the best available hitter in the second round. For example, when the draft reversed in the second round and came back around to me, Chris Davis was still available so I grabbed him. So through 20 picks in the draft, I had the most dominant starting pitcher in the league, and one of the most dominant hitters (and his 53 homers) of 2013.

8th – 10th pick – if you are drafting at the bottom all of the previous here super stat hitters are likely to be taken already, but there will be some viable breakout players available. Giancarlo Stanton went in the third round in my draft. Who did I choose over Stanton in that round? Jacoby Ellsbury, not a bad trade-off.

The best part about picking late is that you get to pick back-to-back players since the draft order reversing and starts the other way. So if you have the 10th pick, you can take a hitter, then with your next pick, take a pitcher. Picking late will at least get you the players you have your eye on right away, because you are selecting two in rapid succession rather than waiting through pick after pick hoping someone you want is still available by the time it gets to you.

Third through Fifth Rounds of the Draft

In my opinion, the middle rounds are where leagues are won so pay attention when it gets to this point in the draft. Doing a little homework ahead of time is advisable.

In the first two rounds, the stat history really drives the picks, but in the middle rounds, you have to start filling out positions so the best available hitter strategy has to end at some point. You can’t simply keep picking great hitters and end up with 10 outfielders on your team and a less than mediocre 2nd baseman.

Again, going back to the hitter versus pitcher debate, starting pitchers can only help your team once every 5 days, so in the middle rounds, you want to start stocking up on the best available position players and this might lead you to select a “dominant for his position” hitting second baseman or shortstop over a much better hitting stat-wise 1st basemen or outfielder.

For instance, in our draft, Robinson Cano went before Stanton, Ellsbury, Votto and Fielder just to name a few, because he was a dominant hitting 2nd baseman over the last 5 years.

As for as really good hitting 1st basemen and outfielders, those positions are stocked. Yes, I took a 1st baseman with my second pick, but he had 53 home runs last year. If not for that, I would have taken Cano, who went 2 picks later. However, based on Cano’s early season stat totals, that would have been a mistake.

By the end of 5 rounds, you should have 4 starting position players and at most, one really good starting pitcher or closer.

Round 6 and Beyond

During round 6 and beyond, you should alternate between finishing your starting position players and finishing your pitching staff.

You need at least 2 really good starting pitchers to win most leagues. In my case, this year I opted for 3, but all have spent time on the DL.

As I have discovered over the years playing around with my all closer pitching strategy, really good starting pitchers anchor your team ERA and WHiP. Without them, an occasional blow-up by a closer can temporarily destroy your stats because those meltdowns count for more because you have less innings pitched on your team.

In theory, closers should have the best ERA and WHiP, however, you would be surprised how many of them give up at least one walk or hit, and a run in each of the one innings they pitch a night, and yet still earn a Save. Just giving up a hit and a run in one inning means your ERA and WHiP for that night is 9.00 and 3.00 respectively. No team is going to win a league with an ERA above the mid three’s and a WHiP much over one point something.

Make sure you have all of your starting position players filled out before you start taking “best available player” for backup positions. If you try that best available strategy throughout the draft, you are going to end up with a weak hitting catcher, second baseman and shortstop.

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General Stategies

High Batting Average

When selecting hitters, I always try to get the higher average hitters rather than the mashers. I'd rather have a guy that hits 20 homers and bats .300 during the season rather than a guy that hits 40 homers and bats .220.

High average hitters also get on base more affecting other stat categories like hits, average and runs scored.

There is usually an inverse relationship between the team that leads the league in home runs and team batting average.


I try to take one of the top closers in the middle rounds. For instance, I took Kimbrel in the 5th round. You can usually wait a round or two more, however, once a run starts on closers, the best ones go fast. However, do not panic. There are always closers that falter and new star closers emerge each season, so if you miss out in the draft, all is not lost.

Transaction Trends

Visit the transaction trends page on your fantasy league provider. This will show you the recent adds and drops in all leagues in Yahoo for instance. You can get some great insight from this page. If you see a bunch of adds occurring for one guy, someone knows something. Either it is a hot prospect, or some other player was injured and that person is moving in as a starter.

So What Have We Learned Here

Winning Strategies for Drafting a Fantasy Baseball Team
Credit: mjpyro

Well, nothing really except that this can get really nerdy fast. However, fantasy teams can add a lot of interest to an otherwise boring season (and game). Let’s face it, baseball is pretty boring. Have you ever sat down and actually made it through a 9 inning game? Even when I go see a major league game at a stadium, I get so bored and so uncomfortable in those seats, that I am out of there by the 7th inning.

To win a fantasy league, requires three things to go your way.

  • You have to draft smart initially
  • You have to be active on the waiver wire to pick-up hot players
  • You have to be lucky

And let’s face it, luck plays a big role in success in fantasy play. Unexpected injuries can derail an entire season and that is not something you can anticipate. Pitchers are especially vulnerable to season ending injuries, which is yet another reason why I shy away from selecting them early.

Always expect the unexpected and do not get down if you have a bad draft. There are always new really good players that emerge every season. Keep up-to-date on baseball news and grab them before anyone else does.

I’ve always said that leagues are won in the middle rounds of the draft and on the waiver wire. My most recent acquisition has been Gregory Polanco even though he hasn’t been called up yet from Triple A. He’s only 23 but is dominating the minor leagues. Before that it was George Springer who is raking the ball.

Currently I am in 4th place in my league, but that has more to do with injuries to my starting pitching and my second overall pick, Chris Davis and Josh Hamilton.

However, I believe that baseball stats revert to the mean, so hot starts cool off and struggling players eventually get back to the their career stats so I think I will be there at the top in the end.



Jun 19, 2014 1:48am
Update: Well, my first round pick is really starting to pay off. He's been lights out his last few starts, and threw a no hitter last night, striking out 15 in the process. So given the way some of the star hitters have struggled this season, I made the right choice.
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