There are two types of teams in a Dynasty League.  You are either a contender or in the process of rebuilding.  The strategy is very different depending the type of squad you are currently rostering.  Sometimes, though, teams think they are contenders when they should have been rebuilding and that can set them back even further. You need to be realistic when you look at your roster. It is great to have confidence in your roster and obviously you are always playing to win, but it can do more damage than good if your team is truly not capable of winning it all. As we write these Strategy Session articles, we find significant overlap with all Dynasty strategies, so we would also suggest reading our Strategy Session focused on Youth and Upside.

Rebuilding:
A rebuilding team is one which realistically doesn't have a chance to win within the season you are currently playing in.  The owner of a rebuilding squad must remain patient while keep their eye on the prize - understanding that a championship squad can in fact be built within a single season (and subsequent offseason).  The first (and often very difficult) step is making a reasonable assessment of your team and its likelihood of competing for a playoff spot.  This is important - overvaluing the overall strength of your squad, or waiting too far into the fantasy season hugely limits opportunity.  To maximize value players must be traded to contending teams at the ideal times (injuries, bye weeks, prior to the trade deadline).  Finding these situations before the other rebuilding teams greatly increases opportunity to maximize a return on value.

In order to capitalize and successfully rebuild, you need to know your fellow owners. Realize their tendencies, who fancies themselves a contender and who doesn't. Aligning yourself with an ideal trading partner is a great way to make a youthful bounty on a deal. You are giving up a player that can help some other team win a championship - a difference maker. For this, you need to be properly compensated with building blocks for your team's future. Don't assume because an owner is in first place that they might not be looking to improve their team. An angle to take with a first place team is that "a potential deal could set their team apart as you head into the playoff stretch". In the back of every playoff contenders mind is "what kind of moves is competitor going to make?" 4) If you are rebuilding, trading an established talent one or even two years early is better than a year too late.
5) As a rebuilding team, you need to acquire young, potentially elite talent in your moves. There is inherent risk in unproven players, which is why a playoff contender can justify moving one or two in a win-now attempt.
There is a delicate balance that Contenders must always be cognizant of. If you give up all of your prospects in order to win, you could be faced with a very hard reality check the following season as your roster quickly turns from dominant to past their prime. However, should you choose to sit on your roster as is, you are taking another risk - the risk that another contender will make a move and put him or herself over the top with a big acquisition.
2) Don't be afraid to pull the trigger. Repeating with the same roster is very difficult.  Moves must always be made.
4) Do not sell out your entire future for one shot at a title. The goal is always to compete for a championship but in a Dynasty league you need to be mindful of your team's future projection.
5) Leverage your position as the contender by creating a market for the young player or players that you are willing to give up. You could get multiple teams offering up their aging stars for rebuilding prospects, leaving you to pick the best package.

A Beast Rule for both Contenders and Rebuilding teams - Mastering the Art of the Throw-in:
In every deal that goes down, one team always takes one more shot to get some additional value. Whether you are the contending team inheriting an aging player or the rebuilding team that is acquiring a young potential Beast, an additional player or pick can make the trade easier for one side to pull the trigger.

It usually works one of two ways: If you are the Contender, you are sacrificing potential for the opportunity to win. To recoup some of your future value that you are giving up, ask for a draft pick or a Dynasty prospect that is not as highly thought of or valued. This is a great way to gain some additional value on your roster - even if the Dynasty prospect you acquire seems like a longshot to have value, keep in mind that Dynasty situations change rapidly. If you are the rebuilding team, you could use the fact that you are giving up proven talent to your advantage. Even though you are acquiring a well thought of prospect, he is still very much unproven. To get the deal done, the contender will likely view a late draft pick or deep bench prospect as a small price to pay in the grand scheme of things. Often times, the throw-in you receive develops into a valuable trade chip or a valuable contributor down the road. With a combination of patience and opportunity, sometimes your throw-in even turns into a Beast.

Bottom line - it never hurts to ask for a throw-in during negotiations, just be careful not to make it a deal breaker.