It's always seemed to me that an inordinate number of trades go down in my fantasy baseball leagues in mid to late May. It certainly makes sense... the tiny sample size of April games has turned into the smallish sample size of the season being more than 25% over. Fantasy owners who were certain their teams were stacked at every position and each category can suddenly see very real holes in their teams that are not going to magically disappear. Many owners who were clinging on to their pre-season sleepers-turned-serious underperformers are finally willing to sell low. Others who'd been scoffing at "fluke" hot starts of certain players are realizing that some may not be so fluke-y after all and may be willing to buy fairly high. The reality of player injuries and demotions has settled in. Meanwhile, the excitement of the beginning of the season has worn off, and things in real baseball feel a little stagnant until June and July arrive, bringing rookie call-ups and real-life trades to alter teams, lineups, and players' fantasy values. Some fantasy owners might just be bored... and while hopefully you play in a league where owners are serious enough that they would not pull the trigger on a big trade mostly to "shake things up," you might still be able to take advantage of the late May doldrums. In any legitimate league, no trade should be made that doesn't help both owners, of course. But you can still make a fair trade while taking advantage of the fact that some owners might be just a little extra desperate to change their teams up, out of either necessity or desire for something different.
Personally I've never been a huge fan of trading in general. I get emotionally invested in "my" players and at times even feel a bit guilty for letting them go. For any of us who do a great deal of off-season preparation for our drafts, it can be extremely difficult to admit mistakes we made with our own teams, or that another team's success is based on anything but dumb luck. I probably tend to hold on to players that are underperforming, and will probably continue to do so, much too long. I often make the mistake of letting past players who I gave up on too soon haunt me and prevent me from making clear-headed decisions in the present. Remember that for every guy you dropped or traded too soon, there are probably a dozen that you cut to make room for a better player who ultimately improved your team. If you are reading this article, I assume you are someone who enjoys trying to predict how well major league baseball players are going to perform at their jobs. Successfully making those predictions can be insanely frustrating, but arm yourself with as much information as possible, both opinion and statistics, and go for it. Take advantage of the articles on this website and use the charts, graphs, and well-researched opinions within them to figure out which players should be bought, sold, or left alone. Will a lot of that information end up being incorrect? Sure. But it will help a lot more often that it will hurt, and should give you an advantage in making trades with less dedicated owners who are not paying as much attention as you are. I still enjoy playing in NFBC-style leagues that do not allow trades at all, because I like the challenge of boiling the fantasy game down to draft plus in-season acquisitions. But if this means that I consider leagues where trading is allowed to be less difficult on some level, then shouldn't I be embracing the opportunity to improve my team by being "better" at fantasy baseball?
Notice everything when making a trade, and remember to look both at the obvious, and beyond the obvious. I always find it a little odd how often folks are desperate to get feedback on their trades, from friends, league mates, or strangers, based on the players involved alone. It simply doesn't make sense to analyze a trade in a vacuum, even if you know the basic parameters of the league. A trade involving the exact same players may be a "win" for side A in one league, and for side B in a different league. I've seen owners ecstatic to pull off a trade despite the fact that they only have room in their lineup for one of the two players acquired. In one of my very deep NL-only leagues, I have three playable catchers and three playable shortstops: six guys to fill five (C, C, SS, MI, U) positions. Meanwhile, three of my five starting outfielders are basically pinch hitters. I am desperate for a decent outfielder and it would probably be worth if for me to trade one of my catchers or shortstops for an outfielder who, on paper, might be ranked a bit lower overall. (Yes, it would be nice to have the depth to cover an injury, but in a league this deep I feel that it's an unaffordable luxury). I will hope that no one notices just how needy I am at OF, and will try to get the best deal possible, of course -- and in a league slightly less competitive where the other owners weren't paying such close attention, I probably wouldn't agree to a trade where I felt I was giving up even a tiny bit of value. But in this case I realize that I'm probably going to have to settle a bit: I know that I need some productive at bats so badly, that if an outfielder who can go right into my starting lineup is even 75% as productive as the shortstop sitting on my bench, it will be worth it for me.
Meanwhile, other owners might be too worried about specific positions that they need to fill. Of course, you should always try to trade from your positions of strength... just remember that you don't always need to take the "position" part of it literally. I still feel like I could have taken better advantage of owners who panicked looking for a second baseman to replace Dee Gordon this season. I think I woke up to offers in three different leagues from owners scrambling to acquire one of my middle infielders the morning his PED scandal broke. I didn't end up making a deal for any of them, but in at least one case, the owner was so anxious to get a new second baseman, that he wasn't even thinking about why he drafted Gordon in the first place: speed. This owner had several points to gain in stolen bases and needed lots of help in pitching, but had more power than he needed. He was so panicked to replace Gordon, however, that he ended up trading a starting pitcher for Jonathan Schoop. I don't think there's a single category this trade will help him in, and all it did was weaken an already questionable pitching staff.
Finally, remember that when making a successful trade, you may need to swallow your pride and be realistic about some of the misfires you made on draft day. Don't be the guy who scares away other teams from trading with him at all because he is still clinging to his pre-season rankings, desperately trying to push deep sleepers gone awry. In one league, I had an owner who for weeks was trying to sell me on the 25 home runs that he swore Adonis Garcia was going to hit this year... right up until the day Garcia got demoted to the minors. I'm particularly amused when a fellow owner quotes the pre-season projections of the "top" fantasy websites when discussing a seriously underperforming player at this point in the season, as if those numbers were some sort of gospel that is destined to become true.
This can go the other way as well. If a player who was obtained at the end of a draft or plucked out of the free agent pool can help your team win, don't avoid a trade just because you feel like you're getting ripped off based on values from the preseason or early April. Realize that values have changed since April 1st, and even May 1st, in many cases rather drastically. In the NL-only league that I referenced earlier, I desperately need a closer. This is a league deep enough that pretty much any player who might even think about getting a save is owned and has been all season... finding saves on the wire is downright impossible. (Tony Cingrani was paid for at the auction and has been on a team all season, for example. Like I said, deep). Meanwhile, I simply don't think that I have a chance to win if I don't add a closer to my team, and quickly. I've realized my only shot to obtain one is probably to give up a solid starting pitcher for the one closer whom I think will be available via trade: Fernando Rodney. Will I be frustrated beyond belief wondering why I couldn't have just figured out in March that Rodney was going to be effective this season and bid on him at the auction? Yes I will. Will it crush a small part of my soul to give up a player who cost four times as much as Rodney did at our league auction? Yes it will. Is it quite possible that Rodney either implodes soon, or gets traded to a team that will use him as a (fantasy) value-less setup man? Yes it is. But if I firmly believe that making the trade gives my team a better chance to win -- and I do -- then I need to pull the trigger. If you can make a trade that you truly believe will help you win, go for it... even if your early-April self would be laughing you right out of the league.