Dynasty Roundtable: The Best Time to Deal

A collaborative staff discussion of dynasty-themed topics in the offseason: When is the best time to deal players and picks?

The Footballguys staff got together to discuss various dynasty-themed topics as we head into the offseason. This series of articles is designed to give you a boost of knowledge on the dynasty front covering several relevant and pertinent topics over the course of the offseason. Below is the first installment of our collaborative discussion.

Other offseason dynasty discussions

As NFL free agency and the NFL Draft come and go, we begin to see more clarity with NFL teams and how they are managing their rosters. As a result, the dynasty landscape evolves as the offseason progresses. What times throughout the cyclical NFL year are best for buying and selling players and buying and selling draft picks? Do you have a general rule of thumb or guide on when you target or sell players vs picks? How do you approach the offseason with your dynasty squads?

Sigmund Bloom
Trading for picks right now is not a good deal. They represent endless possibilities while everyone is still gearing up for the draft. During the rookie draft, trade-ups might be more advantageous when someone is lukewarm about their options when they are on the clock, and it can also be a good time to trade down if you have clarity that your favorite target will be available later. The rookie draft is also the best time to get veterans who might be at or past their prime for win-now runs. Rebuilding teams will often give them away for later picks.

More than timing any market correctly, the most important task for offseason trading is taking stands on which players are at the foot of a mountain of value growth or the precipice of a canyon of value dropoff and acting before it becomes clearer to the hive mind that those players are about to have dramatic changes in value. Get them or get rid of them while you can.

Jason Wood
I'm with Sigmund on being cautious about moving up in rookie drafts right now or acquiring high picks unless you're in a complete rebuild mode. I'll also add the attentiveness and focus of dynasty leagues tend to skew higher than traditional redraft leagues, because it's a more complex game usually played by veterans of the hobby who evolve into the format. That means there are fewer obvious arbitrage opportunities to generate easy value.

I think the best time to acquire veteran talent is during the rookie draft when everyone is under the gun. You need to not only have a handle on your own roster but your league mates. Identify which teams are likely to be playing for the title this year, and which teams likely want to focus on youth and getting back into contention in 2022 and beyond. The teams in rebuilding mode will often be willing to give up high-quality veterans if they fear a key rookie is going to be gone before their pick.

Dave Kluge
Jason, I don't disagree, but I also think the time of year after the Super Bowl and before free agency gives you the most upside when making deals, but it carries the gravest risk. At the beginning of the offseason, you can get guys like A.J. Dillon and Jameis Winston for relatively cheap in startups and trades because the uncertainty is baked into their market value. While Dillon could end up the Packers’ bellcow back and Winston could end up a starter somewhere in 2021, there’s also the inherent risk that both could end up with limited roles. As for the best time to buy and sell players, it all depends on your risk tolerance. If your roster is looking bleak, now is a great time to swing for the fences and hope to acquire some high-risk players like Rashaad Penny, Jerry Jeudy, and the aforementioned Dillon and Winston for cheap. However, if your roster is ready for contention, wait until a few weeks before NFL kickoff to make any big moves. At the time, expected volume and roles should be a bit clearer, and transactions carry less risk.

Jeff Haseley
What about buying and selling draft picks, Dave? Where do you stand here?

Dave Kluge
Well, there isn’t a worse time to target picks than right before the NFL draft. With the dynasty community solely focused on incoming rookies, the value for those potential breakout players will never be higher. My preferred time for acquiring draft picks is midseason. At that time, league managers are focused on the current season, and as a result, draft picks become devalued and easy to acquire.

Jeff Tefertiller
There is a lifecycle as to the value of rookie picks and veteran players. I agree with the consensus here. The best time to buy picks is in the preseason and during the season. The worst time is now until the draft as dynasty players have rookie-itis and love the young players. We, myself included, overvalue the picks as we only see potential.

For the veterans, acquire in the early offseason and sell during the season when everyone needs a steady WR2, for example. We have seen trades of veteran running backs and wide receivers this offseason that are below what I would consider fair value as fantasy players become focused on the NFL Draft.

Andy Hicks
Draft picks are at a premium just before your dynasty draft. Players are at a premium approaching and during the season. I know it's a cliche regarding the players but you should always buy low and sell high. If through circumstance you lose your starting quarterback and have little to choose from on the waiver wire, you are buying high, but have no choice due to a competitive disadvantage. Selling a player after a huge game or if they are aging or approaching free agency and in your opinion will struggle to replicate past glories, at least consistently is the ideal situation. Selling a player after he tore his knee or is at the end of his career and changing teams every season is not so good.

A smart manager tries to accrue draft picks when other managers are least interested in them. In other words, during the season or when they are desperate for a player. Second- or third-round rookie picks acquired cheaply at the right time can be traded before or during your rookie draft by a manager desperate for a rookie and can attract a high-quality starter in return.

Ideally, you try to trade a player away as he peaks or one year before you think he starts trending down. You try to acquire a young player who has the pedigree, but maybe had a tough rookie season and still has upside. If my team has youth, I tend to maybe trade some draft picks away to fill in roster spots. If my squad needs some youth, the reverse. Before the trade deadline, you try and assess next year's squad and find players who have a use in the current year but not much further and trade them if possible. Grabbing young players behind established starters at the same time is also a fun strategy.

Once we hit the offseason, where am I strong and weak now, next year, and in two years? You are in essence playing three different seasons with the same squad and trying to improve all three groups without weakening any. Impossible, sure, but then comes the decision to win this year or build for next or the year after. If your starter goes down, do you have depth? Who are you unlikely to play ever? You are examining your roster from 1-16, 20, or however deep you go.

Troy King
I agree with the others...

I normally look to acquire picks during the regular season because that’s when they are at their lowest value. During the season, fantasy players are mainly focused on assets that can contribute in the present time, so many times rookie picks are an afterthought. I usually look to sell my rookie picks towards the end of the season/ during the offseason. During this offseason, I traded the 1.09 and a 2022 first-rounder for Mike Evans for a team that I believe is a contender. The trend seems to be that rookie picks become more expensive the closer we get to the NFL Draft.

In terms of targeting players, I look to acquire players who had a down season or did not perform up to expectation, who I believe will have a bounce-back season the following year. Players who suffered an injury, whether season-ending or late in the season, also have a value dip which I like to acquire at that perceived discounted price. Examples of players who fit the bill are Clyde Edwards-Helaire, Jalen Reager, and Odell Beckham Jr.

I also evaluate each of my teams to determine whether they are a contender or in rebuild mode. For my contending team, I look to acquire aging veterans who I believe have at least another one to two years of quality production left. A couple of examples of players that I’m targeting are Melvin Gordon III and Adam Thielen. For my rebuilding teams, I look to unload my aging vets and acquire younger players and rookie picks. Examples of some players I’m looking to trade away are T.Y. Hilton, John Brown, and Chris Carson.

Jeff Haseley
What about you, Will? What about during the actual rookie draft?

Will Grant
Like most of the folks here, I think trading rookie draft picks heading into the NFL Draft is pretty difficult. There is always a lot of uncertainty around what a team needs or what a rookie pick will be worth, but with people looking at the draft as the best place to add long-term talent, the last thing anyone wants to do is make a mistake. They will be very conservative in what they are willing to offer, and sellers will be in the better-make-it-worth-my-while mode. Your best bet, if you are looking to move up or down in the draft, is to wait until your actual draft is just about to start or still in the first round. At that point, you have a pretty good idea of who you want and where they should go in your draft. It's much easier and you'll be more likely to find fair value vs. someone looking for a windfall.

For veteran players - trading players for picks is usually best around the midpoint of the season. Fantasy owners who are in the playoff hunt will want to bolster their current team to solidify their playoff chances, and teams who need a miracle are looking to start the rebuilding process now. Buying veterans/solid performers will be key for playoff teams, and acquiring players for next year and beyond will be key for the maybe-next-year teams.

Chad Parsons
It's all about the timing. In the two, three, or even four months leading up to the NFL Draft (and dynasty rookie drafts) there are select hot young rising dynasty players/assets, but generally, rookie picks are all the rage. As a result, the sturdy veterans with locked-in profiles of production and (likely) situations are the pivot plays. The older wide receivers are glaring examples this offseason specifically. Options like Michael Thomas, Mike Evans, Keenan Allen, etc. are wildly affordable compared to their historical profile and production.

If a seller of rookie picks, they peak post-NFL Draft once dynasty players at large can attach prospects to NFL team landing spots, NFL Draft position, and their rookie picks. Once a rookie draft begins -- even on the clock like Sigmund mentioned -- is when these picks reach their climax for trading liquidity and demand.

Flip to when production is valuable and it is the regular season. Running backs with a window as the team's starter have robust value compared to most of the annual calendar, the same with veteran wide receivers who were largely underappreciated months ago. Now, in October/November, they are posting points, winning matchups, and valuable yet again. Future rookie picks are generally undervalued when 12+ months out from being on the clock as well as in-season.

Pivot from the market norm by buying (select) veterans in the offseason and buying rookie picks in-season, while still being a contender with enough production to win and enough rookie picks to offer long-range upside and depth. This is the consistent to-do list smoothie of market exploitation ingredients at play for optimal dynasty general managing.

Jordan McNamara
Now is a great time to trade as activity level is spiking in leagues as startup drafts and rookie draft preparation begins in earnest. Generally, buying rookie picks only gets more expensive as the pick gets closer to the clock, so if you want to move up the board, it's better to do it now than wait until it's rookie draft day. In terms of players, I like to buy safety early in the offseason, while selling situational risk. Players like James Robinson, Logan Thomas, and Jalen Hurts, who have atypical draft pedigree profiles, are classic sell candidates. The profiles I'm looking to add are those with higher job security or longevity.

Adam Wilde
All of these guidelines are good, but I don't believe there is a single time of year that is conducive to acquiring players. Buy windows will vary from situation to situation. I tend to buy players with discounts predicated around injuries. I believe players return to full health more often than not while plenty of other managers are more risk-averse and may sell for a discounted value.

The absolute best time to sell a pick is while on the clock. We all suffer from FOMO (Fear of missing out) and there will be somebody in your league with enough conviction on a rookie to pay a premium for your pick.

Buying future picks is also a way to improve your standing. I tend to try to buy picks two years out. Asking to have a 2022 pick thrown in a deal is a lot easier than asking for a 2021 first-rounder. People can stomach that more-distant throw-in much more comfortably. Assuming trading picks two years out is permitted in your league, I recommend adding this practice to all your trade negotiations.

Questions, suggestions, and comments are always welcome to haseley@footballguys.com

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