Fantasy 101: How to Win Later in Dynasty Drafts

Travis Sherer takes a long-term look at dynasty draft strategy. Hint: No one under 25.

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
Jan. 23: How to Draft Dynasty Prospects

Knowing your strategy to draft for success down the road is an exercise in patience. It requires fortitude, resilience, and pluck—all of which mean the same thing. Nevertheless! It is like a well-played game of chess. A game that you won’t know if you won for at least three to five years and maybe not until 10 years have passed. Are you insane enough to take on such an endeavor?


Draft Mindset

Drafting to win sometime down the road takes more than doing research, creating lists and getting sniped. It takes a certain mindset as well—a tunnel vision that blocks out all other factors and allows you to focus on the most central point. When you consider which player you’ll draft (Player X), you have to evaluate that player against all others with a single scenario: a manager sends you a one-for-one trade offer. You own Player X and they own Player Y. Ask yourself: “Would I trade Player X for Player Y straight up?”

If the answer is yes, you draft Player Y. If the answer is no, you draft Player X. This question is your north star in drafting for the future. It seems obvious, but it’s not. You have to ignore so much!  You have to ignore position scarcity, ignore having too many outfielders, ignore saves, ignore contract status and team status. You have to ignore all the other distractions that go into any other draft you’ve done. Just focus on which player you want the most. If you end up with 10 shortstops, so be it. They should all be younger than 25, and you can never have too many young, talented shortstops.

Now that your head is in the right place, let’s talk about a few rules to help guide you through your decisions to properly gauge which player you’d trade for in a one-for-one deal and pick accordingly.


Rule 1: 2019 and 2020 Do Not Matter

Remember: You are planning for 2021 and beyond, so you don’t even need to fill a full roster of active players in 2019 and 2020. You don’t even need to fill a starting lineup with current players unless there’s something in your rules that says so. Take advantage of that. Go full Sam Hinkie…well…maybe not full Sam Hinkie. That would include a 13-page resignation letter that quotes Elon Musk, Bill Belichick, Warren Buffett, and Abraham Lincoln, among others. Maybe go three-fourths Hinkie—because remember: You aren’t trying to win now. Unlike the former Philadelphia 76ers general manager, you may not be trying to lose, but that doesn’t mean you have to put any effort into winning. Treat your roster as a holding place for assets, some of which will not be in play for another two, three, or four years.


Rule 2: 25 or Younger Only

This rule should be obvious. After the draft is finished, no player on your roster should be older than 25. Anyone who’s older than that will be at the tail end of his prime by the time you are sniffing a playoff spot. This is a much simpler rule to live by nowadays. It was harder 10 years ago when teams thought veterans were more important. Now clubs just cycle through young players on cheap contracts until they find ones worth keeping.


Rule 3: Draft Guerrero, Soto or Bregman

In keeping with Rule 3, you not only need a guy who’s under 25, but he also has to be dynamic. Good thing for you there are four: Vladimir Guerrero Jr. (19), Juan Soto (20), Alex Bregman (24), and Ronald Acuna Jr. (21). With that said, I recommend the first three because even though Acuna isn’t the most talented (Guerrero) or best performing (Bregman) youngster, he is often picked the highest. Now, if you think he is the most talented of the group, by all means, pick him over the rest. I just find his valuation on dynasty rankings odd because it does not seem to be based in any logic.


Rule 4: Draft Forrest Whitley

While there are potentially four top hitters to acquire, there is one top pitcher: Forrest Whitley. The last three pitching prospects with this much talent were Stephen Strasburg, Clayton Kershaw, and Mark Prior. Injuries slowed two of their careers by tampering with their stuff, but no one doubted all three were once-in-a-decade type pitchers. With a potential for five plus pitches, Whitley is of the same caliber. He’s got it all: a great fastball, slider, curveball, and changeup. The only pitch that needs work is his less used cutter. Does he really need it, though? He’s got twice as many pitches as some of today’s top starters (psst…I’m looking at you Luis Severino and Patrick Corbin).


Rule 5: Draft Shohei Ohtani

Can you name another prospect who can contribute at an All-Star level in nine of your league’s 10 categories? Sure, Shohei Ohtani won’t do it in 2019, but you don’t care about 2019, right? Ohtani possesses a level of talent that we see…well, actually, most of us have never seen his level of talent. If you are starting from scratch, you will value versatility, and there is no more versatile player than one who can hit and pitch.


Draft Scenario 1

Now that we’ve gotten the path to winning later out of the way, let’s go over what a couple of successful drafts might look like. A note before we get too far into this: While I advise you to draft the best young talent available regardless of situation, these scenarios have one player in every position who will see time in the majors in 2019—in case your league will throw you out for doing a full Hinkie.

First, we’ll entertain the idea that everything went wrong: You got the first pick. Who do you take?


Pick Name Position Age
1 Mike Trout OF1 27
24 Walker Buehler SP1 24
25 Cody Bellinger 1B1 23
48 Shohei Ohtani DH 24
49 Eloy Jimenez OF2 22

I got one pick into the draft, and I already broke Rules 2 and 3. But we are talking about maybe the best player in the last 100 years, and he’s just entering his prime. Mike Trout, 27, is going to be much better than your average All-Star for another eight to 10 years. You could set the tone right away and go crazy by picking Acuna or Guerrero, but this isn’t rocket science. Make the level-headed play and grab the best player you and I will ever see.

At pick No. 24, who would I rather have: Walker Buehler or Noah Syndergaard? It depends on my strategy. Buehler is two years younger at 24 years old and already showing he can be as good of a pitcher as Thor.

Who is the best non-Cody Bellinger first baseman under age 25? First base is a wasteland for young players. Get the one who stands out, as I did at No. 25.

Like many young players, Ohtani’s value represents a wide spectrum. I’ve seen him pegged in the 30s in some places and in the 70s in others for average draft position (ADP). This puts him smack in the middle of that. And Eloy Jimenez is a no-brainer at No. 49. Not many prospects have his combination of power and performance.


Pick Name Position Age
71 Forrest Whitley SP 21
72 Rafael Devers 3B1 22
96 Wander Franco SS 17
97 Josh Hader P 24
120 Julio Urias SP2 22

My thoughts on Whitley are noted extensively above. For pick No. 72, I went with Rafael Devers, thinking Brendan Rodgers would already be taken. If Rodgers isn’t gone by then, you have a dilemma. They both possess great hitting prowess. I’d probably end up with Devers anyway. After all, they are the same age (22) and Devers already has two seasons under his belt.

Wander Franco is a reach and a steal at No. 96—they call that a paradox. He’s the last remaining player with the potential to be the top prospect as early as 2019. The kid can do it all. And as soon as everyone sees that, he’ll be drafted accordingly. You always need Josh Hader—that’s all I will say about that. At just 20 years old Julio Urias is ready for a bounce-back. No. 120 might be a little early, but it’s worth it for his upside.


Pick Name Position Age
121 Jo Adell OF 19
144 Mackenzie Gore SP 19
145 Bo Bichette 2B 20
168 Franmil Reyes OF3 23
169 Josh James SP3 25

Let’s hear it for more power! Jo Adell carries a Justin Upton comp (hopefully he’s a little more consistent). He’s in Double-A to start 2018 and should be ready by 2019. Mackenzie Gore is the second-best pitching prospect not to have already made his MLB debut. His total package screams ace. Though he’s still playing shortstop, Bo Bichette is likely to settle at second base for the Blue Jays in 2020—just in time for you to be taken seriously in your league. Franmil Reyes brings the power at the plate, and Josh James brings it on the mound, while both have legitimate concerns about harnessing their raw ability.


Pick Name Position Age
192 Casey Mize SP 21
193 Danny Jansen C 23
216 Keston Hiura 2B 22
217 Mike Soroka SP4 21
240 Justus Sheffield SP5 22

If Casey Mize is still available at No. 192, count yourself lucky. He could be in the majors by the end of 2019. It probably won’t happen, because even if he’s that good, the Tigers won’t need him in 2019. They probably won’t need him in 2020 either, but he’ll be up around then anyway. Danny Jansen is one of the better catching prospects in the game, and Keston Hiura has the bat to be a top-tier second baseman if his defense is good enough to keep him there. A couple of additional pitchers in Mike Soroka and Justus Sheffield offer promise with upside of a No. 3.


Pick Name Position Age
241 Dansby Swanson SS 24
265 Jordan Hicks RP 22
266 Willie Calhoun OF4 24
290 Garrett Hampson 2B1 24
291 Robert Puason SS 16

If all young players are lottery tickets, pick Nos. 21-25 in this scenario are those with long odds. The 16-year-old Robert Puason, oddly enough, might be the best bet of them all. Dansby Swanson has been up-and-down in the pros and you’ve got to wonder how much of his value will be tied to defense alone. Nobody throws the ball faster than Jordan Hicks, but can he turn that into Ks? It didn’t even happen in the lower level of the minors. 2019 is Willie Calhoun’s last stand, and Garrett Hampson could be traded at any moment to make way for Brendan Rodgers.


Draft Scenario 2

As in Draft Scenario 1, this example fields at least one player per position who will see playing time in the majors in 2019. Now we’ll do this again, but this time we’ll go with a scenario that you don’t get a top pick. You get a lower-end pick, which is, in my opinion, the better scenario:


Pick Name Position Age
10 Juan Soto OF1 20
15 Cody Bellinger 1B1 23
33 Shohei Ohtani DH 24
39 Eloy Jimenez OF2 22
58 Nick Senzel 3B1 23

This is a beauty of a start to a win-later squad. All are solid hitters with tremendous upside for both average (except Bellinger) and power—and one of them can pitch, too. Soto hit like 10-year vet with his patience and power. Bellinger is the only real high-potential first baseman younger than 25. Jimenez can hit for power and will likely anchor the White Sox offense for years. Senzel is more of a table setter—an on-base machine with average power and a little speed.


Pick Name Position Age
63 Forrest Whitley SP 21
82 Wander Franco SS 17
87 Jesus Luzardo SP2 21
106 Josh Hader P 24
111 Luis Castillo SP3 26

Just like in Scenario 1, I grabbed Whitley, Franco, and Hader. These are staples to starting your win-later dynasty right. Since returning from Tommy John surgery over a year ago, Jesus Luzardo has been lights-out all the way up until a short, unfortunate sample in the hitter-friendly Pacific Coast League. But he’s faced some of the best hitters in the world and came away unscathed in spring. The 21-year-old is a promising young pitcher. The same can be said for Luis Castillo, who finished strong in 2018 after a terrible first half. I did make a mistake with Castillo, as he is 26, but I suppose rules were meant to be broken…when you are too lazy to follow them.


Pick Name Position Age
130 Triston McKenzie SP 21
135 Edwin Diaz CL 23
154 Alex Kirilloff OF 21
159 Josh James SP4 25
178 Casey Mize SP 21

After getting sniped for Gore in this scenario, I grabbed Triston “The Stick” McKenzie. He’s dominated his way to Double-A with tremendous control and swing-and-miss stuff. I picked the top closer in the game, who also happens to be 23, and Alex Kirilloff, who has an impressive approach for such a young prospect (21). And I finally caught up on pitching after making my first five picks hitters by grabbing James and Mize.


Pick Name Position Age
183 Franmil Reyes OF3 23
202 Adley Rutschman C 20
207 Jurickson Profar SS 25
226 Alex Verdugo OF4 22
231 Garrett Hampson 2B2 24

I nabbed Reyes again, as he’d likely be around for before pick 200 and the power potential is undeniable. Adley Rutschman can do it all. He’s the top catching prospect—yes, better than Joey Bart. Jurickson Profar is only 25! He could still get better, folks. Alex Verdugo will be on the Dodgers this year or traded to a team that will play him in 2019.


Pick Name Position Age
250 Nick Madrigal 2B 21
255 Andrew Vaughn C 20
275 Willie Calhoun OF5 24
280 Blaze Jordan P 16
301 Robert Puason SS 16

Alright, it got weird with the last five picks. Only one could actually contribute on a team in 2019 with maybe one more able to contribute on 2020. Nick Madrigal could be in the majors by 2020 if everything goes right. He has the hit tool already and the speed. It’s just a matter of making adjustments to better competition.

Andrew Vaughn is my No. 2 fantasy prospect in the 2019 MLB draft so far. The man is putting up elite statistics in a power conference and already won one Golden Spikes Award. I went heavy on teenager phenoms and potentially the top pick in the 2019 MLB draft. Blaze Jordan gives off a Bryce Harper vibe in terms of power potential (Blaze Jordan also seems like the name Harper would give himself if he changes it). He’s hitting tape-measure shots (500+ feet) with wood bats in major league stadiums—and he just turned 16. Another 16-year-old, Puason, is thought of as the best international prospect (not named Ohtani) in years. Puason is so good, he’s the main reason former Atlanta GM John Coppolella was banned for his international-prospect conduct. He allegedly had a verbal agreement with Puason when he was just 14.



Yes, there are players I took in both scenarios. I did that for two reasons: (1) to emphasize the importance of drafting those specific talents to your team’s future, and (2) contrary to what prospect lists may tell you, there aren’t many good bets for prospects to even make the major leagues, let alone be an All-Star. With the exception of Calhoun, every player/prospect drafted above has that potential. There are more than who I picked out there with this potential, but the choices are limited—and the value is changing.

(Graphic by Justin Paradis)

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.

3 responses to “Fantasy 101: How to Win Later in Dynasty Drafts”


    So i’m curious how you would value ohtani in yahoo’s format where they decided to split him into two seperate players

    • Travis Sherer says:

      That is a good question. He isn’t nearly as essential as two players, although I think he has just as much talent in both areas. I’d want him as a hitter for sure, because I think he’s still undervalued there in all formats. I’d pick him in round 7-8 or so. As a pitcher, you could wait past round 10 to maybe even 12-13 — around the same place as Brent Honeywell.

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