30 Days Until the Ottoneu Deadline

We have reached the MLB trade deadline which means we are just 30 days out from the Ottoneu trade deadline. I would say that means it is time to decide if you are buying or selling, but you should have done that already. I would say it is time to start making trades, but you have probably done that, as well. So here are the ___ things I am trying to do this month, ahead of the deadline.

1. Where I am buying, upgrade my weakest positions. This seems obvious, but managers sometimes get infatuated with the best player on the market rather than the biggest upgrade, and those aren’t the same thing. If you have a stud prospect or a young arm or some other fun piece to trade and have two teams dangling Ronald Acuña Jr. and Freddie Freeman (the two highest-scoring players in Ottoneu this year), the decision on who to take is not as clear as “Acuña is better” (he is), it matters what you are changing. Maybe you have a deep OF and your only 1B is C.J. Cron. Acuña would push 5.14 P/G Kyle Schwarber to the bench, while Freeman would replace Cron. Take a moment before making a trade to look at how a trade changes your lineup and add the most points you can, not the best player you can.
2. Where I am selling, move on from anyone I know I won’t keep. This doesn’t have to mean just taking the best offer you get, but don’t get overly precious about turning down subpar offers for a guy you know is gone after the year. If the best offer you can get for your $50 Trea Turner is a prospect who needs a good end of the season to boost his value and might only be a trade piece for the off-season, that still might be better than holding Turner. I also find that taking seemingly low offers (if they are the best offer on the table) can have some long-term benefits. First, it encourages people to be proactive about making offers. They can’t (well, they can, but they shouldn’t) complain that you gave up Turner for too little if they offered nothing. Second, I think it can help show that you are reasonable in trade talks. At some point, a reputation for only taking offers you clearly win doesn’t help you make future trades. I would never rush to take a bad offer or accept something that wasn’t the best offer, but taking the best offer even if it isn’t what you hoped, can sometimes help.
3. But don’t take just anything. Ok, I know I just said you should take the best offer even if it isn’t what you hoped for, and now I am saying the opposite. Kind of. You still need to have a floor. The combination of #2 and #3 is really saying to make sure you hold your floor but that your floor is low enough. You might want a legit young player for your $89 Soto, but if the best you can do doesn’t include that, the question needs to be, “Am I better off hitting the off-season with this return or with a $91 Soto?” If the offer feels light, but meets that bar, you should really consider taking it. You don’t have to take it today but on August 30? Maybe you should.
4. Try not to be making deals on August 31. Buying or selling, I prefer to be done before then. If I am buying, a player I buy on August 31 only has one month to impact my scoring. Adding Shohei Ohtani to your roster is great no matter when you do it, but Ohtani is literally twice as valuable to you today than he will be a month from today. If you are buying that late, you likely won’t see much of a gain in the standings. As a result, if you are selling, you have a harder time getting a return that late. Either way, I prefer not to have work to do those last couple of days.
5. …Unless something comes up on your roster. You don’t want to be making a trade on August 31, but what if your star 2B goes down on August 29 and someone is shopping a rental Ozzie Albies? Well, in that case, be ready to make a deal. Don’t forget what we talked about in #4 above – over 30 days, replacing a 4.5 P/G backup 2B with a 5.8 P/G Albies is worth about 40 points. Is that worth trading for? Sure. Is it worth giving up a ton of future value? Only if you think 40 points will make a difference.
6. …Or if you are in a H2H league. This is another exception to #4. In fact, in head-to-head leagues where I am confident I can make the playoffs, I prefer to wait until later in August to make deals. There is risk here – you can’t wait if a player you want/need is being actively shopped and you might miss out. But in those leagues, September is so much more valuable than the rest of the year that saving some trade pieces to fill in gaps right before the playoffs can be an advantage. Maybe you get an injury or have a young pitcher shut down, or have a couple of MI go cold. The later you wait to make a deal, the more information you have about wait you need for the playoffs and the more targeting you can be in acquiring the right player, not the best player (see #1).
7. Communicate with everyone. Check-in with everyone in your leagues. Who are they dealing? What are they looking for? Even if you are buying and they are buying (or vice versa) you never know where you might find a deal. I just swapped Colton Cowser for Jacob Misiorowski and Jordan Lawlar in one of my leagues. I am playing for next year, as is the team I traded with. We are both looking for the same thing but differed on values of these players and found a deal with both really like. Don’t ignore another manager just because you think they want to do the same thing you do.
8. Be kind. It is easy to get frustrated when someone doesn’t reply to an offer. Or makes an ask you think is crazy. Or rejects a deal you think they should take and then trades that player to another team for a return you think is worse than what you offered. But it does you no good and it hurts your long-term relationships with your league-mates. Be respectful, be kind, and be forgiving. Assume other managers are smart and that if they disagree with your valuation, there is a good reason for it.