A lot of fantasy managers are going to choose to go for the title aggressively, with the thinking that anyone can win in a 60-game sprint. But if you are realistic with yourself and the state of your franchise, and you don’t see yourself among the elite of the league today, there is an opportunity this season to speed up the rebuilding process.
Traditionally at this point in the season a lot of teams would have already been looking to the future. If you are playing a 20-team keeper league, under normal circumstances, maybe six managers are still adding pieces, and a bunch of other teams have already sold off players. But if you were to begin today as though you are already rebuilding, you could potentially have as many as 19 trade partners, all competing against each other for your players. It would take another manager choosing to follow your lead before you would even have competition.
With an unprecedented short season upon us, I think now would be a good time to discuss trades and some of the lessons that I have picked up over the years. I am approaching this from a dynasty perspective, for someone who wants to start looking towards the future. The season is already winding down as odd as that sounds, and a case could be made that this would be an excellent year to rebuild if you are not already set up to compete.
KNOW WHERE YOU STAND
The first step in deciding whether it is time to throw in the towel is making an honest assessment of your franchise compared to the rest of your league. It is important that you can accurately gauge the strength of your team and make the appropriate adjustments. Sometimes that will mean adding players, other times that will mean trading players away for future assets. I generally try to avoid being a middle of the pack team in a long-term keeper league. Ideally you are either aggressively going for the title or aggressively setting up your future. The most common mistake I see managers making is not doing anything. Unless you are sitting on a well-oiled machine, there will always be improvements you can make in one direction or another.
CAST A WIDE NET
If you are playing a long-term league, over time you should develop friendships, rivals and others who you barely speak to. I have never found it beneficial to burn a bridge because I want to have the ability to trade with everyone. When you are considering making deals for the future, take a look at every roster in the league. Generally, if I am sitting near the bottom of the standings, I will start by reaching out to the person in first place, and work my way down the standings. Before I contact anyone, I will have gone over their roster, thought about what they have that I want, and figured out what I might be able to offer. I am not making any trades during this process, just beginning discussions and planting seeds.
SET THE MARKET
Once you have determined rebuilding is the best choice, I have often found it beneficial to be the first team to throw in the towel. The main reason for this is I want access to every team in the league before they start moving the players I expect them to. Another advantage is that if you are the first team to make a now-for-later deal, you will be able to set the trade market for the rest of the league. It will be difficult for anyone to go far away from that original deal’s value without causing a stir in the league. I would recommend beginning negotiations in private before actually announcing your intentions. You would like to avoid being overwhelmed with trade offers and already have a decent idea of what you are after and what it might cost.
DON’T PLAY GAMES
Once you have begun negotiating, I have often found it best to be honest. Tell the person what you are after and why. You don’t have to be overly honest; I just would not recommend saying anything that can be looked back at in a negative light. The last thing you want is to gain a reputation of being hard to deal with, or even worse, a slime ball who only talks trades when it is obviously beneficial to them. Your goal is to make solid, relatively fair offers and make the negotiating experience as painless as possible for your trade partner. I have spent many hours, days, weeks and months involved in painstakingly slow negotiations where both people are fighting for every inch. I would rather find out in a few minutes if there is something to work with.
STAY AGGRESSIVE
Once you have announced your intentions to rebuild, and made the first trade, it is important you do not then become complacent. That first trade is going to awaken a lot of managers in your league and it is important you stay engaged with all the trade talks that you started. You can also use this opportunity to drive up the prices for other managers desperate to make a splash. Sometimes I will even give the image that I am a loose cannon and could make a deal at any second. This of course is both accurate and gamesmanship. There are times where it is best to lay in the grass and watch while others are making moves. Generally, though, I have found it more advantageous to give the appearance that you are involved at all levels.
TARGET HIGH UPSIDE ASSETS
High upside assets can come in different shapes and sizes. It can be anything from a young Major Leaguer on the verge of superstardom to a late-round prospect pick. Anything that could theoretically turn into a game changing piece. Most of the time that means going after already established elite prospects and paying with Major Leaguers that aren’t necessarily part of your long-term plans. But something like a late-round prospect pick might be very easy to acquire as a throw-in piece. I would rather have that lottery ticket than a mid-level prospect or Major Leaguer that I don’t think is capable of becoming a cornerstone piece for a championship team. When you are in the midst of an aggressive rebuild, you want to acquire as many high upside assets as possible.
LOOK FOR OPPORTUNITIES
Often times when you are an active participant in a deep keeper league’s trade market, opportunities will open up that you had not considered. Maybe that comes in the form of someone making you an intriguing offer that you had not considered. Possibly it involves being brought in as the third party to get a deal over the line. Maybe someone is willing to trade you one of their best players, but you already have a good player at that position. There are many possibilities but the more engaged with the process you are, the more you will find yourself discussing big trades. When you are a team on the rise with only a handful of desirable assets, you have to embrace any moment you can get a trade partner to discuss legitimate pieces.
GO WITH YOUR GUT
Once you have gained enough experience you need to be able to trust the feeling inside you telling you there is something wrong. I have often found myself deep into negotiations and trying to talk myself into a deal that deep down does not feel right. It may be the value I am receiving or potentially I do not value a good player the way they are hoping I will. If I find myself in that position, I will just be honest with my trade partner and let them know I need more to get it over the line. You can’t be afraid to walk away from a deal if it is not sitting right with you. Sometimes this will happen even when the offer looks fantastic on paper. It is extremely important you are confident in your ability to judge talent. And once that skill is established, listen to yourself.
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