Stop me if you’ve heard this one before – “I love the trade deadline!”
Everybody does, I think; there’s excitement, lots of communication and speculation; if you are pushing for a title, it’s nice to get the pieces to help fill in gaps, or if you are rebuilding, it’s nice to find another piece you can hope will pay dividends in the future.
This feeling naturally extends to the fantasy baseball trade deadline.
While its real-world counterpart gets constant attention and hundreds of thousands of words written pertaining to the buyers, sellers, and pieces involved, fantasy teams get no such love.
Well, “got” no such love. Hopefully, today we can right this wrong and assist teams in making deadline moves – or, at the very least, give you something to ponder as the deadline approaches.
Of course, this article will be focused on a dynasty-league setting, and before you ask, the stats referenced in this article are current as of Thursday, July 31, 2025, and yes – I am aware there are only batters mentioned here. Read the whole article and you’ll get an idea for what I’m planning for pitchers.
Let’s get busy!

What should a buying team be looking for?

To answer the question very bluntly, the very best pieces you can find in order to fill the gaps on your team.
In some cases, this may be “a healthy catcher.” In other situations, the answer may be “a fourth outfielder.” For some, “more home runs” is a target, while for others, “a third baseman worth rostering” is the bar to clear. Either way, you need to be looking for the best possible avenue to fill the gap.
This may look like Aaron Judge filling in that gap in your outfield; conversely, it could be getting hyped to pick up Yoán Moncada in a spicy sicko mode league.
No matter the situation, you’re looking for the best players available to meet your needs. As you have no doubt learned, though, a league “Trade Block” post or vague text shot into a league Discord or groupchat may not be as thorough or diverse as you would hope. How can we combat the clever salesmen pitching their wares, half-in managers trying not to look desperate or foolish, or the year’s cellar-dwellers doing anything to avoid lowball offers?

Drew’s ‘Do’s for Deadline Dealing

Drew’s Tip #1: Reach out to every manager in your league – directly if possible.

Pop quiz, hot shot: how are you going to know if a player is available in a trade situation?
If you answered “I’ll just check the league trading block,” that’s a great start, but hardly the final say-so.
If you said, “I just assumed my leaguemate Taylor Corso (84 percent of you play in a league with this man, don’t lie) wouldn’t trade Cal Raleigh,” you are doing this wrong, plus you know what they say about people who assume. (They don’t have direct answers to their questions.)
If you answered, “I’m going to reach out to everybody as directly as I can and ask about specific players or at least start a dialogue,” congratulations – you have the right idea.
Okay, sure, this is going to be a little bit of work, but at this point, you are 500 words into an article about how to best tackle the trade deadline for your fantasy league, so I can only assume you are not above putting in the work.
Don’t want to come off as annoying? Don’t be annoying! A “Hey pal/chief/buddy/dude/brother/Taylor Corso, hoping to talk trades when you have a minute” in an email/Discord message/text message/face-to-face conversation puts the ball in their court and also expresses interest.