Fantasy 101: How to Win Now in Dynasty Drafts

Travis Sherer takes a look at the art of the dynasty draft and outlines his strategy for drafting a "win now" team.

Dynasty Draft Preparation:
Jan. 11: The 10 Commandments of Dynasty Drafts
Jan. 16: How to Win Now in Dynasty Drafts
Jan. 18: How to Win Later in Dynasty Drafts

If you clicked on this article, you are interested in the road less traveled.

When engaging in a dynasty draft, the number of managers who: (1) are building for the future already, (2) have convinced themselves to employ the ill-conceived strategy of straddling the fence by picking old and young players, or (3) do not have a plan, completely outnumber those drafting for instant gloryjust add water.

Drafting for the here-and-now is an unpopular strategy because most managers do not want to admit that they will not be able to build a dynasty that lasts decades and rules their leagues (if only given the chance). Baseball is too random for something like thatunless you’re playing with a bunch of rejects and a fat kid. Admittedly, I am guilty of this logic. I use the more popular strategy to play for the future. I choose to buy a ton of lottery tickets, convincing myself that I am the smart oneI only play the Powerball when the jackpot is more than $300 million. To do so any other time is a waste.

So, let’s lay out a winning draft strategy for 2019 and 2020, shall we?


Rule 1: Power is a Must

Watching ’80s action movies is a favorite pastime of mine. It brings me back to my childhood. Even though I grew up with Predator, First Blood, and Road House, and have seen them more than 10 times each, whenever I watch them now I think: “Is all that muscle really necessary?” That is the question the other managers in your league need to be asking when they see your roster. They need to be offended by your muscle.

Even in today’s game where everyone hits 20 home runs, being the best at power means you win at least three of the five hitting categories every time. The same thing goes for pitching. If you go for power pitchers with a low ERA and WHIP, that also means you win three pitching categories every week. I’m going to show you how to get both later on, but you have to commit to winning now. Do not think you can use a single pick for the futurethat is what a prospect draft is for, assuming your league has one. Like The Expendables, you need to pick up all those old action heroes who post the gaudy power numbers (both at the plate and on the mound) at the end of the draft, when everybody else is searching for bargain youth.


Rule 2: Pick a Centerpiece

You get three names: Mike Trout, Mookie Betts, or Jose Ramirez. Make no mistake: If you do not get one of those three guys, you will start slow out of the gate. Maybe five players have a track record of being able to contribute heavily in all five categories of a 5×5 league. These three players show the best combination of those five skills and are the most likely to continue to do so for the next two or three years. Another one is Francisco Lindor. The last one is maybe Alex Bregman, if he decides to run as he did in 2017. What about Manny Machado? He’s a lesser version of Bregman. Did you know that 2018 was his first year posting a .900 OPS? It just happened to be in a contract year. Go figure.

Of course, there are a couple of younger potential options: Ronald Acuna and Juan Soto, but you do not have time for sophomore slump candidates. Vladamir Guerrero Jr is also out of the question for the same reason. Once again, you do not have time for a player to learn the majors. It could take the entire two years to be Trout, Betts, or Ramirez. And two years is what you are hoping to get out of this before the luckier “win later” drafters start to chase you down. By all means, draft the young guys if they fall to you in the or third round, but do not reach for them when there are five potential candidates who are more likely to provide what you are looking for.


Rule 3: Draft Shohei Ohtani

If Shohei Ohtani hadn’t hurt his elbow, he would be a first-round pick in many dynasty drafts. Can you imagine the value of a player who, in a given year, could be an all-star pitcher and/or hitter? For some reason, he is now damaged goods despite hitting better than Acuna, Albies, and Soto in 2018.

I know I said you don’t have time for potential sophomore slumps, but Ohtani is different. Why is he different? The most important reason: He’s cheaper. You won’t have to draft Ohtani until between the fourth and sixth rounds. He has faced more scrutiny and media attention than Acuna, Albies, and Soto combined, all while succeeding in something that none of them can do collectively. He made changes to his swing during spring training that helped him go from being a Nippon Professional Baseball MVP-caliber hitter to an MLB-all-star caliber hitter in just a month. Having a DH who is probably the second best DH (J.D. Martinez is No. 1) for the next two years is a pretty good consolation prize, especially if he goes back to pitching in 2020 and can contribute there while also hitting bombs and stealing bases.


Rule 4: Draft Josh Hader

Just like burying people in home runs and RBIs, you want to bury them in strikeouts. Nobody does that better than Josh Hader. If you want to win now, you need to take advantage of the Delosh Betader theory and get at least two elite, non-closing relievers to pad your ERA, WHIP, and strikeouts. When it comes to pitching categories, leave no doubt to the fact that you will win every week. There are two ways of doing that: (1) Draft a lot of high-end starters or (2) Draft a couple of high-end starters and a lot of high-end relievers.


Rule 5: Draft J.T. Realmuto

Can you name another catcher who will still be good by 2020? Buster Posey no longer counts. Let one of the other two “win now” managers scramble to take him or Gary Sanchez after you grab J.T. Realmuto. It seems silly, but to effectively achieve either a “win now” or “win later” strategy, you have to be “that guy.” The guy everybody says, “of course he picked Realmuto in the sixth round,” like that is something to be ashamed of. Yes, he will be 28 soon and he is a catcher, but he has very few games under his belt for a catcher of his age. He is the best bet to contribute for you during your window.


Draft Scenario 1

Now that we have gotten the rules to winning now out of the way, let’s go over what a couple of successful drafts might look like. First, we’ll entertain the idea that everything went right for you: you got the first pick in the draft! Who do you pick?


Pick Name Position Age Contributing Stats
1 Mike Trout OF1 27 AVG, HR, SB, R, RBI
24 Freddie Freeman 1B1 29 AVG, HR, R, RBI
25 Corey Seager SS1 24 AVG, HR, R, RBI
48 Noah Syndergaard SP1 26 ERA, WHIP, K, W
49 Whit Merrifield 2B1 30 AVG, SB, R


This is a fantastic first five rounds of a 12-team draft. There is a core in place that can compete in every category, including the best player in baseball. Freddie Freeman has the possibility to age like Joey Votto, which would make him valuable for the next five years. You could take advantage of Corey Seager’s poor 2018 that was cut short by injury. It’s a little light on pitching, but as I’ve preached before on this site, I know a way to fix that. Noah Syndergaard is an injury risk, but picking innings eaters later on, in addition to long relievers, can take the sting out of Thor.


Pick Name Position Age Contributing Stats
71 Shohei Ohtani DH 24 AVG, HR, SB, R, RBI
72 J.T. Realmuto C 28 AVG, HR, R, RBI
96 Josh Hader P1 24 ERA, WHIP, K
97 Justin Verlander SP2 36 ERA, WHIP, W, K
120 Yasiel Puig OF2 28 HR, SB, R, RBI


So, a DH in the sixth round? A DH that can steal bases and who will pitch in 2020! Yes, please. Like I said earlier, if Ohtani had not gotten injured, he’d be picked in the top 12 picks. His injury casts doubt on his overall ability and future role. Take advantage of it if you can. This is pretty late for Ohtani, but I’ve seen top keeper lists that project him being picked as high as 100. Grab Realmuto here and feel lucky. This is about where he lands on all the lists and if you can squeeze him here, you are in good shape. In the eighth round, I got one half of Betader, and I will grab the other half 10ish rounds later. Justin Verlander is a gamble here, not because of his ability, but because he may not be around by pick 97. Some don’t think so, but it has been my experience that during dynasty drafts age plays a much larger factor than it does in top-300 keeper lists. Yasiel Puig here is also potentially a stretch. It depends on how your league is set up: how many people dislike him and how many see he’s already 28?


Pick Name Position Age Contributing Stats
121 Aroldis Chapman CL1 31 ERA, WHIP, K, SV
144 David Price SP3 33 ERA, W, K
145 Daniel Murphy 1B, 2B 34 AVG, HR, R, RBI
168 Franmil Reyes OF3 23 HR, RBI
169 Josh Donaldson 3B1 33 HR, R, RBI


My first closer is a masculine closer! Chapman continues my theme of high-K/low WHIP relievers to accompany Hader and the half dozen I’ll pick down the road. David Price remembered that he is a good pitcher in 2018. I think he has a couple more seasons of that 3.50-4.00 ERA in him (and he might remember that he’s an innings eater too). Daniel Murphy in Colorado spells trouble for opposing teams. Remember when I said you want other managers to be offended by the power you have? That’s where Franmil Reyes and Josh Donaldson come in.


Pick Name Position Age Contributing Stats
192 Michael Fulmer SP4 26 ERA, K
193 Jose Leclerc CL2 25 ERA, WHIP, K, SV
216 Nelson Cruz OF4 38 HR, R, RBI
217 Kyle Seager 3B2 30 HR, R, RBI
240 Chad Green P 27 ERA, WHIP, W, K


I’m banking that Michael Fulmer’s second half was not a fluke and he remembered how to pitch again because when he does, he is above average. You combine above average starters with the relievers I’ve picked in this draft and you have amazing. Speaking of which, Jose Leclerc may not close for Texas in 2019, but he’s the best reliever on the roster and he should be treated as such. More muscle coming in Nelson Cruz and a bet that Kyle Seager will bounce back with pick 217.


Pick Name Position Age Contributing Stats
241 Adam Eaton OF 30 AVG, SB, R
265 Brandon Belt 1B, OF 30 AVG, HR, RBI
266 Dellin Betances P 31 ERA, WHIP, W, K
290 Brad Peacock P 31 ERA, WHIP, W, K
291 Ryan Pressley P 30 ERA


With my round 21 through 25 picks, I went with three relievers who will help me chew up innings to turn my lack of a fourth starter into an asset, especially since I believe Brad Peacock will get around 10 spot starts this year. I also grabbed a backup outfielder who is one of the best OBP guys in the league when healthy and will steal a base or two. I also grabbed Mr. Boring: Brandon Belt.


Draft Scenario 2

Now we’ll do this one more time, but this time we’ll go with a scenario that you don’t get a top pick. You get a lower end (last) pick:


Pick Name Position Age Contributing Stats
12 Aaron Judge OF1 27 AVG, HR, R, RBI
13 Chris Sale SP1 29 ERA, WHIP, W, K
36 Paul Goldschmidt 1B1 31 AVG, HR, SB, R, RBI
37 Corey Seager SS1 26 AVG, HR, R, RBI
60 Eloy Jimenez OF2 21 HR, R, RBI


OK. I break some of my Dynasty Draft Commandments in the first five rounds of this (drafting a 31-year-old and 21-year-old rookie), but there is a reason for that. Managers who want to win now are in a much better position to do so if they pick in the top six of a draft. If they are in the bottom half of the draft, they have to start to gamble to make up some of that production lost by not having a top player in round one. Aaron Judge is the start of that: power is still a must and Judge has more power potential than anyone else in the league. With my second pick, I could have gone with Bryce Harper or Javier Baez and doubled down on the power, but both are on my do-not-draft list because I believe they are overpriced in 2019 drafts. Instead, I went with the best power pitcher in the game. Some say it’s Max Scherzer, and they may be right, although Chris Sale puts up the same numbers as Scherzer despite facing a DH. Seager is a common pick in both drafts but for the only reason that he represents the last opportunity to get an elite SS. If I were picking in the middle of a round, Lindor would be an option for round one. I’m not a big fan of win now managers picking Trea Turner because they lose a chance to get a true power hitter.


Pick Name Position Age Contributing Stats
61 Shohei Ohtani DH 24 AVG, HR, SB, R, RBI
84 Josh Hader RP 24 ERA, WHIP, W, K
85 Khris Davis OF3 31 HR, R, RBI
108 Justin Verlander SP2 36 ERA, WHIP, W, K
109 Craig Kimbrel CL1 30 ERA, WHIP, K, SV


See above for what I think about Ohtani. There will be some picks that are on both draft scenarios. They are here because I’m reaching for them in both drafts. I believe in their production that much. Hader is another holdover. He is a must for any win now team. He provides a layer of stability to your rotation that you will not appreciate until you have itespecially if you combine him with more high-usage, elite, non-closing relievers. Between Judge, Eloy Jimenez and Khris Davis in your outfield, you’re set for power in 2019 and 2020. I’m making another gamble that Verlander will be around in the 10th round. Some people don’t think he will, but once drafts start and they see his age is 36, he will start dropping.


Pick Name Position Age Contributing Stats
132 Zack Wheeler SP3 28 ERA, WHIP, K
133 Blake Treinen CL1 30 ERA, WHIP, K, SV
156 Daniel Murphy 1B, 2B 34 AVG, HR, R, RBI
157 Danny Jansen C 23 AVG, HR, R, RBI
180 Josh Donaldson 3B1 33 HR, R, RBI


I struggled on deciding whether to go with Zack Wheeler or Josh James with pick 132. Ultimately, I see James as a Hader type pitcher, so that would mean a rocky road in 2018 as the Astros figure that out. I hope he does become a number-two starter, I am just not sure he has the repertoire or command. With Blake Treinen, I got my second elite closer to combine with my elite non-closers and we’re well on our way to a top pitching staff. Murphy has one more year of eligibility at 2B and he’s in Coloradoexploit that. In this draft scenario, somebody sniped me for Realmuto, so I went with the next best thing: Danny Jansen. He’s now the clear-cut starter in Toronto after they traded Russell Martin. A bit of a late bloomer, Jansen can hit and he’s going to be in an exciting lineup.


Pick Name Position Age Contributing Stats
181 Julio Urias SP4 22 ERA, K
204 Jose Leclerc CL3 25 ERA, WHIP, K, SV
205 Nelson Cruz OF4 38 HR, R, RBI
228 Kyle Seager 3B2 31 HR, R, RBI
229 Garrett Hampson 2B2 24 AVG, SB, R


Picking Julio Urias at 181 is a bit of wishful thinking, I understand that. I do not think he’s likely to go this late, but I also wouldn’t rule it out. He’s probably in the top 150 of 75% of dynasty drafts. I just feel like this is an opportunity to point out there is an opportunity to get his dominant talent late, even if it isn’t quite this late. He may be on an innings limit, but he was great in a very small sample of 2018 and, if you follow the reliever recipe I have been preaching for nearly 3,000 words, you should be fine pitching-wise. Seager represents insurance for Donaldson. Third base is so deep nowadays that you can get powerful hitters here very late, making good bets like these two older gents priced very reasonably. Garrett Hampson represents the only try at getting steals. This is another byproduct of picking 12th. You have to make sacrifices when you can’t get one of those top four or five guys who can do everything.


Pick Name Position Age Contributing Stats
252 Chad Green OF5 30 ERA, WHIP, W, K
253 Greg Bird 1B2 26 HR, R, RBI
277 Dellin Betances P 31 ERA, WHIP, W, K
278 Brad Peacock P 31 ERA, WHIP, W, K
303 Ryan Pressley P 30 ERA, WHIP, K


These picks look frighteningly similar to scenario one, and that is for a reason: nobody drafts elite, non-closing relievers. Scoop them up late and thank me later. Greg Bird is the only one that is different. This is his do-or-die year. Either he breaks out and this is the steal of the draft, or he flames out and you find someone else.



Either draft scenario here shows a great staff with an excellent combination of starters and relievers that can get to 35 IP per week with top-tier production without a hassle. You’ll also have a power level that nobody can match without seriously damaging their pitching because you’ve also got all the potent non-closing relievers.

Now that you’ve drafted a slightly old, high-powered offensive and pitching machine, you should be on the lookout for prospects who can jump into the majors at any time. Take advantage of flipping those guys to the “win later” owners for players who are producing right now. Also, scour free agency all year to pick up one more starter, even if it is just one who is having a lucky year.


(Graphic by Justin Paradis, @freshmeatcomm on Twitter)

Travis Sherer

All Seattle Mariners fans have learned the future is all we have because the present is always too painful. I am Western Washington University alum, a local sportswriter, an official NCAA basketball statistician, a freelance radio and television production statistician, and a minor league standup comedian. Follow me @ShererTravis on Twitter.

One response to “Fantasy 101: How to Win Now in Dynasty Drafts”

  1. theKraken says:

    Re: #4 – I don’t think there is much precedent for those multi-inning RP not breaking down in pretty short order which makes them a shaky dynasty asset. The same is true of Cs. While JTR is the top dog today, he wasn’t a year ago – that would have been Gary Sanchez. Here is some food for thought – I alternated Kurt Suzuki and Tyler Flower for the last few years which cost nothing – the production I got was probably more than any single catcher. My strategy is to allocate 2 roster spots to the position and profit if you aren’t lucky enough to somehow have a good C fall into your lap.

    One final point that I will make is that format matters a lot. In points leagues things are a bit different.

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