We’re around 40% of the way into the season, so you should be getting a clearer picture of where your dynasty/keeper teams are at in terms of if they are contending or not. Now, if you’re in a H2H league, your standing and record may not accurately reflect your team’s actual potential. If you’re in a H2H league I would highly recommend going to the standings page in your league and clicking on the season stats tab. This page effectively shows your standing in the league if it were a roto league. Now, of course, it’s not a roto league, and you shouldn’t be playing your roster like it is, but this might offer a good sense of where your team is really at. For example, there’s one league I’m in where the team currently in fourth place is 5.5 GB of first, but in second place by a half-point on roto standings, in the top 2 or 3 of all but a few categories. As such, that team should be adding, expecting to contend. In that league that team is also the two-time defending champ so they were likely expected to contend at the beginning of the season anyway, and nothing dramatic has changed on their roster to expect it to be any different this year.
However, regardless of if they are expected to contend, they (and you) should be evaluating your team and figuring out if you are a legitimate contender or not this season. There’s no prize (typically cash or otherwise), for being a meh team. Given that, evaluate your team, see where it’s at and then, take action.
While this happens more often in fantasy than in real baseball (though I really don’t understand why it doesn’t), make trades earlier rather than later, no matter if it’s a roto or a head-to-head league. In real life, for example, teams in need of bullpen help who are contending should be doing things like trading for David Robertson from the Cubs. He’s going to be traded to a contender, so why bother waiting?
The same is true in dynasty and keeper leagues. While contracts and salaries add another component more like real-life baseball to this depending on your league design, if a player is not a part of your next contending roster, then look to move them. Now – this means you also have to figure out when your roster will contend and what you believe it will look like. Is it this year? Next year? Realistically a few years in the future. This can be hard to figure out and is very heavily impacted by league rules, size, etc. But, regardless, figure this out, and figure out what your roster needs.
Now, obviously, dynasty and fantasy trades take on a different shape than real-life trades, but there is never any reason to wait to make a move to either help your team contend or to keep moving towards rebuilding. Indeed, if you know where your team is in terms of potentially winning the league, then striking early to add a player that will help you win now is helpful in that you can get the player before other teams decide they are going to push in future players to win now and are willing to make an offer that might top yours.
If you’re clear that your route is to keep retooling and to trade away players that will not help you when it is time to contend, sometimes moving early can help, yet other times it can be a disadvantage. The tension here lies in if you wait you may get more teams going for it and so have more teams that want to acquire the player you are trading away to really make strong offers.
On the other hand, if the top tier of the contenders in a league pulls away from the rest before the trade deadline, especially in roto, then you are left with fewer teams wanting, and perhaps even needing to acquire those pieces may dimmish.
This is why it’s important to not only analyze your team’s position and actual skill level, but also all of the other teams in your league. Not only can you find who it might be best to trade with no matter your situation, but also figure out how your team fits in with the overall contention picture since, of course, contention is not just your team but how it fits in the league as a whole.
So, all that to say, as your league develops be sure to stay active in trading as you evaluate your team, its position in the league, and the positions of the other teams.