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Winning Strategies For Your Dynasty League Startup Draft

Starting a fantasy baseball dynasty league? Prepare for your 2019 fantasy baseball dynasty drafts with Ellis Canady's guidance on draft strategies to win with a look at our RotoBaller Expert mock draft results.

Some people enjoy playing fantasy baseball one season at a time, drafting a new roster every year. Others are fascinated with drafting a team and managing it year after year towards multiple championship trophies. The latter individuals are best suited to play in dynasty leagues. For rosters to be competitive annually, they have to possess players that are primed for longevity. To do that, sacrifices will need to be made at some point, and that starts at the draft.

The draft: everyone loves it. “It’s the best part of the fantasy baseball season,” many people have stated. Before you get into your full player rankings and nominate/select the players that you love, make sure you have a strategy in mind and stay mostly dedicated to it. Without an awareness of your internal fantasy manager tendencies or even a basic strategy, you will be stuck in limbo trying to figure out where to go.

Everyone wants to compete now, but most fantasy managers generally fall into one of three categories when starting a new dynasty league draft. They either want to win now, win now but pick up some young guys they like, or sacrifice immediate success for long-term dominance. Each category has its pros and cons, but one provides a better long-term approach to success than the other two. Using the recent RotoBaller Way Too Early Dynasty Draft, we will identify a couple of examples of each category.

 

Infatuated With Youth (Young'un)

This drafter builds his team with nothing but youth. We are talking about players just reaching their prime and younger. It may seem like they are fascinated with all the young stars; however, they are building for the long haul.

There are a few positives to this recommended strategy, aside from the obvious fact that you do not have to worry about getting older. The primary benefit is that you are collecting assets that some of the “Drifter” and “Old-Timer” managers will want when they realize they will not win this year. The biggest unsaid positive is that the cost to acquire increased value is quite minimal. While other managers are collecting backup pieces for their roster in the draft, you are collecting upper-tier prospects.

However, do not draft every prospect in the minors. Draft the ones likely to get the most helium, which is mostly hitters. If you have a choice between a pitcher and a hitter, go with the hitter. There are a few reasons for this.

To start, hitters can boost their stock tremendously in one season. If they have a letdown year the following season, there is just a little bit of skepticism. However, pitchers can have a great year but follow it up with a mediocre season, and 90% of the league won’t touch that player until he shows the skills again. Plus, it takes longer for the pitchers to develop into the studs you want them to be. During that time, there is always a possibility that an injury will plummet their value.

Of course, not everything is going to be rosy with this strategy. The Young’un will need to sacrifice the first or second season (depending on your activity level) to develop the team that will lead to championships every year. It will take time and require you to be more active than most. But the result will be well worth it.

Using the RotoBaller Way Too Early Dynasty Draft as a model, we see that a couple of managers came close to replicating this strategy. While, no one fully represented the concept to the fullest, JB and Troy’s drafts closely resembles the ideal approach. (Click on image for a full-sized draft board)

JB, picking from the first spot, is the closest definition of a Young’un, finishing with an average age of 23. Through the first 10 rounds, JB drafted solid young players already in the majors like Ozzie Albies (third round), Rafael Devers (fourth), and Jack Flaherty (sixth). In round 11, he started his prospect collection by selecting Pete Alonso and finished with 11 prospects, five of which were pitchers, including Touki Toussaint (15th round), Mitch Keller (16th), Triston McKenzie (20th). While it isn’t preferable to have that many prospect arms compared to bats, every single one of the pitchers he selected are very close to the majors. This gives him plenty of marketable value.

Troy built a roster with an average player age of 25. He only had nine prospects, but he did keep his team very young with selections of Eloy Jimenez (fourth round), David Dahl (sixth), and Forrest Whitley (eighth). The one intriguing decision that the strategy wouldn’t support was the selection of 30-year-old Tommy Pham in round nine. It seems like a slight miscue with so many young studs still on the board. However, it could also have been strategic to get a power/speed asset that he could trade midseason. Afterward, he got back on track with plenty of young assets in the likes of Tim Anderson (10th round), Keston Hiura (12th), and Jo Adell (23rd rd).

One cautionary note about this strategy. Without action, this drafter could fall into a false sense of eternal prospect love. Snap out of it! Prospects are assets to be used as anything else to improve your roster.

After the draft, the next step is to have a plan to market your players to continue to build up the value of your roster. Timing is an essential ingredient when obtaining value. Also, you do not have to do that in one fell swoop. Some of the assets you receive in one trade can be flipped to someone else for something of more value than your original player.

Here is a series of transactions that can get you towards something of value. You can trade one of your solid prospects to the Drifter for one of his solid starting pitchers who is just reaching 30 years of age. You don’t need this player, but you could certainly flip him to the Old-Timer who is going for the league’s first championship flag. In exchange, you might receive one of his young underperforming guys or an injured player lost for the season (Corey Seager in 2018), both of which are more valuable than the original prospect you drafted.

Whenever the other managers come to the crossroads of needing important decisions/categories answered, the Young’un will be there. He is a purveyor of required items. A tradesman, if you will.

 

Compete Now (Old-Timer)

As the title illustrates, the ultimate goal for this drafter is to build a team that can win in year one. This roster is comprised of plenty of proven players that will likely include many veterans. This owner is not distracted by the latest fad of prospects that are getting plenty of helium.

The positives of this strategy are that you have a roster filled with proven players immediately. The first few years are your prime competitive opportunities to plant a championship flag in your front yard. The only trading will be to fill blank spaces and immediate production. There is no time for speculation picks.

Unfortunately, once the old geezers run out of steam, you’ll have to transition to the bottom of the rankings and start your rebuild looking for the next young studs to use as a foundation, most of which have already been picked over by the Young’uns.

When looking at the RotoBaller Dynasty Mock Draft, there is a clear individual that fall into this category - Andy. He has a roster built to risk it all and win now.

Andy is all in. He demonstrated his determination with selections of Max Scherzer, Clayton Kershaw, Justin Verlander, and Joey Votto in the first 10 rounds. With an average player age of 29, it is no surprise that there are 14 players on the roster 30 years of age and older. There is a bit of a hiccup in this analysis in the middle rounds. Jesus Luzardo (14th round) was likely selected for his tremendous upside, and he should have a rotation spot to start the year.

If you were to play a game of ‘One of these things is not like the other one,’ you would win if Keibert Ruiz (16th round) was your selection. It is possible he gets called up, but that is speculation. That is a word Old-Timers don’t like, unless we’re gold-mining, of course. Andy finished back on track by picking players like Nelson Cruz (15th round), Justin Turner (17th round), and Michael Brantley (19th round). Once the competitive wind is removed from the sails in a couple of years, it will be tough to rebuild around Christian Yelich and Manny Machado.

 

Caught In Between (Drifter)

The ultimate goal of this drafter is to compete now, but at the same time, they want to dabble in the fountain of youth. Actually, maybe they want all the young players, but deep down they want to compete now as well. Caught in between, this drafter will forever perform in the middle class if a serious course correction isn’t initiated. Yep, downright Purgatory.

Can these drafters be saved? Yes. Say it with me now. Yes, they can. A little louder now: YES, THEY CAN!

The trick is timely recognition. I am never a fan of giving up on a season, but if halfway through the year you find yourself at the bottom, you need to start making moves before other managers have run the options dry.

This strategy, unfortunately, puts you at a point where you’ll have to make an important decision about your roster in the first year of existence if you are unable to compete for the trophy. One option is to double-down, selling off the young talent you have for assets to help with a run at the title the following year. The other option is to undergo an overhaul by trading your aging talent to the Old-Timer for any younger options they may possess (Hmmm, Keibert Ruiz comes to mind).

The problem with both of these choices is that it delays your ultimate goal. When you double-down, you’ll have one more shot at the trophy the following year. However, win or lose, your team will have to undergo an overhaul that might take a few years to recover because your players will be hanging out with the likes of Steven Tyler and Mick Jagger (OLD). On the other hand, if you initiate the overhaul, you’ve wasted a year, and it might take you a few years to acquire the talent to be competitive again as others are ahead of you in the process.

Both of these choices could be resolved at the draft table by committing to a strategy as either a Young’un or an Old-Timer.

Understand that there are various degrees of Drifters, which might also be called the gray area. There are quite a few of the RotoBaller Dynasty Mock Draft participants that fall in this category. Some might lean more Old-Timey with some young flavor while others are predominantly Young’uns with a little old-fashioned vibe. Anthony would be considered the former, while yours truly would fall into the latter category.

Aside from the elite players in the first three rounds, Anthony appeared to fully embrace the win-now mentality with selections of Dee Gordon, Chris Archer, Aroldis Chapman, Jesus Aguilar, and A.J. Pollock amongst the first twelve picks. However, he then started taking a few speculative picks in Ian Happ (13th round), Brent Honeywell (15th), and A.J. Puk (18th). Yes, these are very good dynasty choices and were likely selected for their potential upside but they deviate from the layout of the roster. Anthony returned to a more win-now strategy by taking advantage of aging late-round talent in DJ LeMahieu (20th round), Robinson Cano (23rd), and Mike Moustakas (25th).

This writer’s draft went according to the Young’un plan with selections of Vlad Guerrero Jr. (second round), Gary Sanchez (fourth), Nomar Mazara (fifth), and Yoan Moncada (sixth). There must have been a blackout, a fall, and a severe bump to the noggin in round 11. That is the only thing that can justify three straight picks on players whose average age is 33 in Zach Greinke, Blake Treinen, and David Price.

Admittedly, it was a matter of competitiveness. Everyone wants to have their cake and eat it too. Everyone wants to win. This writer is no exception. It is very tough to sacrifice the first season. However, just because you’re going younger the first season doesn’t mean that you are necessarily sacrificing the year. Stay active on the waiver wire, trade, and remain competitive.

 

Keys to Success

The Young’un is the best route to go when starting a dynasty league. Start your roster with youthful exuberance and own the market on all the prospect studs that other teams will want. Choose more bats than arms. Then you can start trading and improving the value of your team by acquiring players with top-10 round value for the price of prospects chosen in the 15th to 25th round. This will allow you to contend for the title for years with an actual dynasty squad.

If somehow I haven’t convinced you to do the right thing and start your league as a Young’un, you need to be all-in as an Old-Timer. Do not try to keep a foot in both waters; it will ultimately lead to a premature rebuild. It’s too early to think about rebuilding a dynasty team shortly after a draft. Just know that as an Old-Timer, once your players' competitive years expire, so will your team.

 

One Last Note

Many individuals will contend that dynasty leagues don’t last very long, so competing in the first two years is ideal. While that is always a possibility, it shouldn’t be the sole deciding factor on how you manage your team. If this does occur in one of your leagues, take it as a sign that the league wasn’t worth spending another year in. There are many dynasty leagues out there.

Find one and DOMINATE!

**The opinions of the author are his alone and do not attempt to represent what each manager was thinking while they were drafting their team.

**The theme song of this article is Bone Thugs-N-Harmony - Crossroads. That's right. Regardless of where you are in your draft strategy, you will encounter some crossroads. I’ll see you when you get there.

More 2019 Fantasy Baseball Advice




REAL-TIME FANTASY NEWS

Jonah Coleman

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Colt Emerson

Mariners Promoting Top Prospect Colt Emerson to Major Leagues
Darius Slayton

Lacking Long-Term Upside for Dynasty Managers
Keaton Mitchell

a Prime Dynasty Handcuff Option Entering First Season in L.A.
Jadarian Price

Looks Like the Running Back of the Future in Seattle
Isaiah Bond

Dynasty Outlook Clouded by Uncertain Role in Cleveland
James Cook III

Remains a High-End Dynasty RB1 Entering 2026
Lamar Jackson

Poised for Bounce Back Season in 2026
Bucky Irving

Expected to Be Ready for Training Camp
Kyle Williams

Deep Threat Kyle Williams Facing Uphill Battle for Playing Time
Michael Pittman Jr.

Could Receive Short-Term Value Uptick in PPR Leagues
Stefon Diggs

Chiefs, Commanders Could Make Sense for Stefon Diggs
Will Howard

Dynasty Value Dealt a Blow
Jaylen Warren

Should Benefit From Veteran QB's Return to Pittsburgh
Drew Allar

Could Continue to Hold Dynasty Value
Pat Freiermuth

Could See a Small Dynasty Bump With Veteran QB Returning
DK Metcalf

A Dynasty Sell Candidate With Veteran QB Returning?
Bones Hyland

Wants to Stay in Minnesota
Mike Conley

Hints He Will Continue Playing Next Season
Kevin Huerter

Iffy for Sunday Night
Caris LeVert

Questionable for Game 7
Duncan Robinson

Back on Injury Report Ahead of Game 7
Larry Nance Jr.

Likely Out Sunday Due to Illness
Munetaka Murakami

Fantastic First Season Continues With Two More Homers
Cristopher Sánchez

Cristopher Sanchez Dazzles With 13-Strikeout Complete Game on Saturday
Aaron Rodgers

Signs One-Year Deal With Steelers
Blake Snell

to Undergo Elbow Surgery on Tuesday
Clay Holmes

Could Miss Around Three Months
Jose Altuve

Exits After Swing
Corey Seager

Absent With Back Spasms on Saturday
Jeremy Lauzon

Misses Saturday's Practice
Mark Stone

Doesn't Practice Saturday
Josh Manson

Misses Practice, Considered Day-to-Day
Brent Burns

Day-to-Day Ahead of Conference Finals
Cale Makar

Considered Day-to-Day
Alex Lyon

Likely to Start Game 6 Against Canadiens
Owen Power

Available Saturday
Isaac TeSlaa

Can Isaac TeSlaa Carve Out a Larger Role in Detroit Going Forward?
Troy Franklin

Facing Uphill Battle for Playing Time in Denver
Trevor Lawrence

Should Trevor Lawrence Be Valued as a Dynasty QB1?
Courtland Sutton

in Line for Reduced Role in Denver?
Trevor Story

Hits the Injured List With Groin Injury
Blake Snell

Likely to Need Elbow Surgery
Duncan Robinson

Nets 14 Points With Four Triples
Cade Cunningham

Contributes 21 Points in Game 6 Win
Jalen Duren

Bounces Back With Double-Double
Anthony Edwards

Finishes Season-Ending Loss With 24 Points
Victor Wembanyama

Tallies 19 Points in Friday's Win
De'Aaron Fox

Highly Effective in Blowout Win
Stephon Castle

Shines in Series-Clincher
Kyle Schwarber

on a Heater, Hits Two More Homers to Take Major-League Lead
Clay Holmes

Suffers Fractured Fibula on Friday Night
Blake Snell

Heads to 15-Day Injured List
Austin Reaves

Could Command $40M Per Year With New Contract
Jalen Duren

Available to Finish Game 6
Yanic Konan Niederhauser

Not Expected to Be Ready for Start of Next Season
Jalen Williams

Declares Himself Healthy for Conference Finals
Terrence Shannon Jr.

Will Play Friday Night
Kevin Huerter

is Available for Game 6
Duncan Robinson

is Returning for Game 6
Caris LeVert

is Cleared for Game 6 on Friday
Blake Snell

Scratched From Start on Friday for Undisclosed Reasons
Max Fried

Heading to Injured List With Elbow Bone Bruise
CFB

Julian Sayin Looking To Build Off Of Strong Debut Season
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College GameDay Set for First Three Weeks
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Jeremiah Smith Aiming For Ohio State Receiving Records
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Keshaun Singleton Projects as Auburn's WR1
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Jeremiah Cobb Impresses New Auburn Staff
CFB

Alberto Mendoza Very Likely to Start for Georgia Tech
CFB

Charles Woodson Jr. Commits to Michigan
Jordan Westburg

to Have Season-Ending Elbow Surgery
Melquizael Costa

Set For UFC Vegas 117 Main Event
Arnold Allen

A Favorite At UFC Vegas 117
Daniel Santos

Set For UFC Vegas 117 Co-Main Event
MMA

Dohoo Choi Returns At UFC Vegas 117
Juan Diaz

Set To Make His UFC Debut
Malcolm Wellmaker

Looks To Bounce Back
Christian Edwards

Set For His UFC Debut
Modestas Bukauskas

Looks To Get Back In The Win Column
Tarik Skubal

Resumes Playing Catch, Ahead of Schedule?
Lane Hutson

Contributes Two Assists in Game 5 Victory
Nick Suzuki

Amasses Three Points in Crucial Victory Thursday
Juraj Slafkovsky

Dishes Out Three Assists in Game 5 Win
Carter Hart

Stops 31 Pucks in Series-Clinching Win
Pavel Dorofeyev

Enjoys Second Consecutive Multi-Goal Game
Shea Theodore

Records Two Points in Game 6 Win
Mitchell Marner

Scores Special Goal in Series-Clincher
Ryan Johnson

Takes Over as Canucks GM, Sedins Promoted to Co-Presidents
Drew Helleson

Won't Play Thursday
Radko Gudas

Unlikely to Play Thursday
Jeremy Lauzon

Remains Out Thursday
Mark Stone

Misses Third Consecutive Game
EDM

Kris Knoblauch Fired as Oilers Head Coach
CFB

Virginia Tech Lands Commitment from Four-Star QB Peter Bourque
Byron Buxton

Scratched on Thursday With Hip Soreness
Cal Raleigh

Heading to Injured List With Oblique Strain
Francisco Alvarez

has Knee Surgery, Expected to Miss Eight Weeks
Quinn Hughes

Finishes Postseason With 15 Points
Cal Raleigh

Exits With Apparent Side Injury on Wednesday Night
Juan Soto

X-Rays Come Back Negative on Juan Soto's Ankle
CFB

NFL Veteran Tom Moore Joins Iowa Coaching Staff
CFB

Can Cam Cook Dominate in Return to Big 12?
CFB

ACC, Big 12 Support 24-Team College Football Playoff
CFB

Anthony Colandrea Looking to Elevate Nebraska Back to National Contention
CFB

Kwazi Gilmer Set for Big Impact at Nebraska
Justin Thomas

Trending Well Ahead of PGA Championship Despite Concerning Form
J.J. Spaun

Trending Up Ahead of PGA Championship
Adam Scott

Riding Strong Form Into PGA Championship
Patrick Reed

Looking to Make Another Run at PGA Championship
PGA

Sungjae Im Looks to Build on Strong Finish at Truist Championship
Sam Burns

Must Keep Ball in Play at PGA Championship
Jordan Spieth

Looks to Complete Career Grand Slam at Aronimink
Brandt Snedeker

Not the Best Option for the PGA Championship
Rasmus Hojgaard

a Volatile Option at PGA Championship
Maverick McNealy

Seeking Better Start in Philadelphia
Harry Hall

a Boom-or-Bust Option at Aronimink
Hideki Matsuyama

Attempts to Improve Over 2025 PGA Championship
Scottie Scheffler

Looks to Defend PGA Championship at Aronimink
Nicolai Hojgaard

Wants to Keep Momentum Rolling in Philadelphia
Ben Griffin

Attempting to Bounce Back After Truist Championship
CFB

Transfer Defensive Lineman Devarrick Woods Commits to Clemson
Harris English

Will Need His Putter to Thrive at Aronimink
Akshay Bhatia

Creative Flair Could Show Itself in Philadelphia
Keegan Bradley

Knows the Aronimink Golf Club Well
Si Woo Kim

Struggles at Truist Championship
Gary Woodland

Can Continue Incredible 2026 Season at PGA Championship
Xander Schauffele

In Excellent Form Heading to PGA Championship
CFB

Isaac Brown Has All-American Upside in 2026
CFB

Nyck Harbor Heading into Breakout Year?
CFB

Notre Dame, USC in Discussions to Resume Rivalry Series
CFB

Jaron-Keawe Sagapolutele Has Eyes on ACC Title
CFB

Ahmad Hardy's Gunshot Wound Not Viewed as Career-Threatening
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