About two months ago, I was asked by a member of the local league I commish to replace an inactive owner in the league he commishes. I replied that I don’t have the time to monitor another team, but if all I’m asked to do is respond to trade offers and ensure I maintain a healthy active lineup (I totally failed at that task), then sure, I’ll take over the team. This is a keeper league in its inaugural year that I was actually asked to join before the season began, but declined for several irrelevant reasons. The league rules are relatively standard, with mixed rosters, 14 teams, and a limit of three keepers. An auction was conducted to roster players and keepers could only be selected from players acquired via the auction, with a salary $5 above their auction price.

Not surprisingly, the team I took over was pretty bad. It had some surprising gems, including a $1 Aaron Judge, but lots of crap and the team languished in the bottom five. I barely did anything with the team, aside from bidding on a potential closer at some point, along with rejecting a bunch of bad trade offers. But the trade deadline comes on August 20, and that means it’s quickly time to look at the standings, then your roster, and assess if you have a shot at the money or not. To dump or not to dump is the question.

Obviously, I have nothing on the line so I’m a bit biased, but the team is weak and with a thin free agent pool, it appeared impossible to ever get this team into the money. So it was an easy call to dump, and that’s when the ethics and integrity issues arise.

I have only participated in a keeper league once, and in that one time, I didn’t even remain for the second season. So, I have never actually played a season, selected keepers, and then entered the following year with a list of keepers with which to surround during the draft or auction. However, I do know that if you have no shot at the money in a keeper league, then every player you own at a non-keeper price is worthless to you. Ideally, you trade off all your pieces to improve your keeper situation next year. Unfortunately, that likely means ensuring the rich get richer and really pissing off the rest of the league.

So this is what just happened…

A week or so ago, I reviewed all the rosters and auction salaries and made a short list of the best keepers in the league. I generally only cared about $1 keepers and focused on hitters. Turned out, every single one of the five keepers I listed belonged to the same team…ya know, the one in first place, of course (who is also a member of my local league). So I emailed him, told him exactly who I was interested in and which of my players were off limits as potential keepers.

The top two keepers in my mind were Cody Bellinger and Yoan Moncada, both with $1 salaries, keepable next year for $6 each. While I preferred Bellinger, he had little interest in trading him, so the focus shifted toward Moncada. As we continued to discuss possibilities, I posted a message on the league message board with my intention to trade my stars for keepers. In a keeper league, this is the best strategy as teams fight for your best players. Though that was my hope, it didn’t happen. I got a couple of offers from one team, all terrible, and I quickly declined. That was it.

So back to the first place team. In my mind, anyone I was not going to keep had no value to me. So he could ask for every player that was an upgrade and if that was what he required to send me Moncada, then sure, we have a deal!

I logged on today to find the following offer made to me:

Yoan Moncada for Jake Arrieta, Gary Sanchez, Josh Donaldson, and Robinson Cano

Wowzers, that’s a lot for Moncada. But who cares? None of those players are at prices I would considering keeping, so if that’s what I need to give up to acquire a top keeper for next year, that’s what I’ll have to pay. It’s not like anyone else made any real offers to compete anyway.

Since I would need to replace all those stars and don’t feel like searching the free agent pool, I asked the Moncada owner to send over the guys he’s benching/dropping to make room for his new collection of stars. So the final offer included Jonathan Lucroy, Ariel Miranda, and Chris Davis, to go along for Moncada.

Accepted.

After I asked the owner to send over those replacements, I said I hope this doesn’t piss off the rest of the league. I genuinely meant that because it sucks when these types of trades occur and the standings are potentially affected in a dramatic fashion by someone at the bottom of the standings.

Sure enough, I got an email soon after from the commish questioning the trade. Knowing the two of us, he wasn’t suspecting collusion, but still felt like I gave up wayyyyyy too much for Moncada and was none too thrilled.

So what am I supposed to do? The way keeper leagues are set up, this is just a side effect of the structure. Whether I finish in 11th place or 13th place, it doesn’t matter. If my non-keepable players have no value to me, why wouldn’t I just give up whatever is requested to secure a guy I considered one of the top keepers in the league? Should I have negotiated with the first place owner? What would have been the point? It’s not like I need to save my stars for another keeper trade. We could only keep three players, and one of them would be Judge. I have several other good options for a second keeper, so I don’t need any additional keepers after Moncada.

So keeper league players — Did I act foolishly? Is this truly ruining the integrity of the league, as the commish claimed? Should I care about how a trade affects the standings, even if I am looking out for the best interest of my team and improving my position for next year (am I really supposed to reject a trade because I think other owners will be pissed?!)? Should I really have negotiated with the first place team to perhaps give him two to three players, instead of four? Is this just what happens in keeper leagues and there’s nothing one can do about it? And last of all, is there really any reason to hold onto non-keepable players if you’re headed for a non-money finish?