Strategy Session: Winning Leagues is More Fun Than Winning Trades

I was originally planning on writing about a different topic today, but I was inspired by a back-and-forth I had with a fellow league member about a deadline trade on Sunday night. There are still far too many owners out there who concern themselves too much with whether they "win" a particular trade - and this only gets exacerbated by Twitter. If it's within the first two months of the season and you're just making deals to increase the total amount of fantasy value on your roster, winning trades is more important. Once you get past June 1, it becomes more difficult to evaluate a trade that is described to you in 140 characters or less because there could be additional factors that come into play that we just don't know. However, overall value is still very important at that stage.

But we're now in August, the time of almost every trading deadline and trades are no longer black-and-white from a value perspective. In fact, once you shift into the last two months of the season, the context of the trade becomes even more important than the value being received. In roto leagues, there are going to be some stat categories that you're going to be nearly locked into at this point. If you're not within 10 HR of any other team (either above or below), then dealing away a power hitter may not have any effect on your team. And this only becomes more obvious when you're dealing with categories like steals and saves. On top of that, there's also price or contract status when you're dealing with keeper/dynasty leagues to further complicate things.

I'll go through two examples of trades I've personally made in the past few days and how this all applies after the jump...

Trade #1: I deal Emilio Bonifacio and Ernesto Frieri for Yu Darvish and Rickie Weeks

This was the trade that sent me on a path to write this post. I got an initial offer from a team for Bonifacio, giving up Weeks and two non-closer relievers and later on I added Frieri in order to try and land Darvish. This led to the owner accepting the trade and sending me this message:

"I don't really get how this helps you, since I don't see Darvish as having much value this year or next, but why not I guess. Good luck man!"

First of all, I disagree with his assessment of Darvish's value. He may not be as valuable as I thought he would be coming into the season, but ZiPS has him projected to finish the season with 15 wins and 222 strikeouts. That's still valuable even if his ERA is over 4 and his WHIP is around 1.4. But, that's neither here nor there - and for the record, Darvish has been the 63^rd best SP on the ESPN Player Rater in 2012. Second of all, there are keeper ramifications for this deal as well. Bonifacio, Frieri and Darvish are all eligible to be kept until 2015 (it's a 16 team league, we keep 10 players each w/ no keeper penalties) and Weeks cannot be kept past this season.

So, in a vacuum, I think Bonifacio and Frieri will have more "value" than Weeks and Darvish over the rest of the season and that's without even taking into account the fact that Weeks is a rental. But more importantly, I don't care. Like I said earlier, the context of the trade is even more important than the value. Let's talk about the additional context here. My team has 123 steals, which is good for first place in the league. The next team down has 113 and they are the only other team in triple-digits. My team also has 102 saves, which is also good for first place in the league. The next closest team to me in saves has 82. So even though I also traded Addison Reed a few weeks ago, I still have plenty of cushion left to win the category. Finally, I may be around 50 strikeouts back from the next cluster of 3 teams in that category, but it's a 1500 IP cap and I'm at least 50-60 innings behind them. This means, it will essentially turn into a K/9 category at this point and Darvish will help me maximize those remaining innings enough that I could catch all three of them (I also have Brett Anderson, Shaun Marcum and Jhoulys Chacin coming off the DL to help there).

But, what about my keepers for next year, you say? First of all, as a rule of thumb, if I'm competing for a title, I'll worry about next season when it comes. Second of all, my potential keepers are strong enough that I would not have kept Frieri and Bonifacio would have been one of my end guys to think about. My eight definite keepers right now are Mike Trout, Bryce Harper, Buster Posey, Mark Teixeira (guaranteed), Alex Rodriguez (guaranteed), David Price, Johnny Cueto and Kenley Jansen - so Bonifacio would have been in a group with Jason Motte, Michael Cuddyer, Trevor Bauer, Shaun Marcum and Matt Harrison. In other words, I'll be fine.

In conclusion, trading Bonifacio and Frieri will likely cost me no points over the rest of the season. Adding Weeks and Darvish could help me gain 6-8 points, by my account. And when you think about it like that, it becomes a no-brainer. Right now I've got a 24.5 point overall lead in the league and if these two guys do what I think they should do the rest of the way, I just locked up a title.

Trade #2:

I deal Albert Pujols, Andres Torres and Bobby Parnell for Shane Victorino, Lorenzo Cain and Ryan Dempster.

I'll keep this one shorter since it's similar to the first description except that this league is a redraft, so there are no keeper consequences. Right now, my team is in first place in HR (by 19) and RBI (by 22), so even with losing a stud like Pujols, I should still be able to get by without losing any points in those two categories. On the other hand, I'm 2 wins away from 3 points, 3 stolen bases away from 2 points and 17 strikeouts from 3 points. Being out of first place by 6 points right now, if I gain where it's reasonable for me to gain, I have a much better shot at winning a title with these three role players than I do with my stud.

Now, in a vacuum, this trade would not be something I'd generally be all that interested in. Unless my team has been ravaged by injuries and I have no choice, I do not like being on the quantity end of a quality-for-quantity trade. But with the dynamic of my roster and where I am in the standings, I have very little chance of winning the league if I don't make a move and the starting pitching market is extremely tight. Plus, in my Ahead of the Curve column from Friday I talked about Scott Feldman and his very attractive schedule the rest of the season. Turns out, because Ryan Dempster couldn't find his passport for a road trip to Toronto, he got pushed back a day, and into what was Feldman's assumed schedule.

Well, that ended up being more long-winded than I anticipated, but I hope it was a helpful reminder of something that seems so simple, but is so difficult for some owners to do. In August, trades don't always have to make perfect sense when described in 140 characters -- sometimes it requires a deeper look. If the person I'm negotiating with wants to win the trade, that's absolutely fine with me -- I'd rather win the league.

Follow me on Twitter at @dynastyguru.