Do you lack depth? Is that why you are making the trade? Before you make a trade to get more depth in one position, stop yourself and think 'despite the fact that I need to trade for a guy in a certain position, am I getting the better players?' If the answer is no, don't do it. You're probably looking to trade with the wrong team.
ALWAYS trade fairly when you are trading across different positions. If you really want to make a big difference on your team, it won't necessarily happen with a single trade. Thus, to get more tradable assets, you are going to need to make a few 'fair' trades. If you make these, other managers will get the feeling that you are a trustworthy trader. Once you have made your fair trades to acquire depth in the positions you plan to exploit, wait to see what others lack.
Now, turn your attention to another team. Find who lacks depth at a certain position. They will likely be willing to trade and lose if it gets them more 'depth'. It is one of those nonsensical logics in fantasy hockey which managers tend to do to get the feeling that they're actually doing something healthy for their team.
Obviously, if they are a good manager, they will be unlikely to trade some talented stud who's on a cold streak for some unproven player who's on a bit of a roll. Therefore, do not risk breaking down the trade by sending an insulting offer. The number one priority at this stage is to create the illusion that the other team is - at best - getting a fair return. Once you have worked this out, you should end up with a slightly better roster overall.
At this stage you should probably not rush into another trade. Give it a week or two then start to think about things. I stress this because A) you need to see how your previous trade is working out and B) you don't want to appear like you're trying to ravage the league of good players.
Let's review the steps of how to win a trade:
Step One: Assess your teams strengths and weaknesses
Step Two: Make a fair trade to give more depth to your weak areas
Step Three: Make another trade, preferably with a different manager than before, to help them get 'depth' in which you slightly win
Step Four: Repeat the process when suitable
Obviously some leagues are different than the one's I'm basing this on, and so, I'm expecting everyone to use their head whilst trading. My main concern is that you don't make too many trades and end up losing talent. As a rule of thumb, I'm assuming everyone reading knows a thing or two about the players in the NHL and their fantasy worth. Good luck!
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