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Keeper League Trade: Going all in and knowing when to bail

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Ray discusses a few trades he made in one of his keeper leagues over the past few weeks.

Gary A. Vasquez-USA TODAY Sports

I have written here several times about the New York based UBA NL-only 4 x 4 keeper league I participate in with 11 other owners. Last season, I went all in after rebuilding in 2013, only to finish in 4th place.....in the money, but the season was a disappointment after I dealt several cheap keepers. You can read about how that all went about in the two articles linked below:

The cost of "playing for this year"

The cost of "playing for this year": Building a winner for 2015

This season, I came out of the draft without a first baseman and a closer, so my intent was to try to deal for them early in the season. Luckily, one owner had already announced prior to the draft that he was rebuilding in 2015. His rebuild began in the offseason, and has continued in the first two months of the season.

I had approached him soon after the draft indicating that I was interested in trading for his closer Kenley Jansen ($24 S2) and his first baseman Paul Goldschmidt ($45 S2). He made a trade about a week into the season, dealing Padres closer Craig Kimbrel ($33 S2) and Reds first baseman Joey Votto ($28 S2), and in return he received a $20 L2 Anthony Rendon and a $5 S2 Dilson Herrera.

We started trading trade offers via text soon after he made that deal, and I honestly went back and forth about whether to start dealing my cheap assets this early in the season, as my team went back and forth between 5th and 6th place. But, as my team started performing better and inching closer to being in the money, I decided to begin the trade discussions for both Goldschmidt and Jansen.

When discussing trades, there is a bit of a cat and mouse game that goes on sometimes. It is a tactic than can work at times, and work against you in others. Sometimes you get "I need player X in the deal or there will be no deal" or "here is my best offer". I also got the old "last chance to get Goldschmidt before he goes". When player X is severely undervalued, it is never easy dealing him, so the response would go something like "I think I am going to sit tight for now. I am not sure my team can compete this year anyway." Player X in this situation is Rockies third baseman Nolan Arenado, who I own at $15 for this year and next.

The team that is in rebuild wants to acquire as many cheap assets as he can, but he can't trade all of his assets for minor leaguers or rookie prospects, because a team full of young, major league prospects is likely to disappoint and not compete. So, the rebuilding team needs some established players, who are performing well, but who are also cheap.

Again, the trade negotiations went back and forth for weeks. He knew who I wanted, and I knew who he wanted, or who he was targeting. That usually comes out very early in the negotiations. In this league, we have an in-season salary cap of $315 ($260 at the draft), so trying to trade for a $45 Goldschmidt and a $24 Jansen and fit them under the cap while trading cheaper assets can be difficult.

The players he was targeting were a $15 L1 Arenado, a $10 S1 Kolten Wong and a $15 L1 Marcell Ozuna, in that order. So, for me to get Golschmidt and Jansen, I needed to give up a corner hitter for Goldy  and a pitcher for Jansen, and in return receive a middle infielder for Wong, and an outfielder for Ozuna. So, the trade wasn't going to be a 2 for 2 trade. It would be much larger.

When the negotiations got serious, they started out with me asking for "just Jansen", He came back saying "let's include Goldy" and we went from there. I forget how I did it, but somehow I was able to keep Arenado out of the deal, and that has proved to be the right call. So here is what the final deal looked like (my team is appropriately named Rays):

Rays gets: Jayson Werth Was from Holliston Donkeys
Joe Panik SF from Holliston Donkeys
Derek Norris SD from Holliston Donkeys
Paul Goldschmidt Ari from Holliston Donkeys
Kenley Jansen LAD from Holliston Donkeys
Holliston Donkeys gets: Jay Bruce Cin from Rays
Marcell Ozuna Mia from Rays
Kolten Wong StL from Rays
Tyler Moore Was from Rays
Mike McKenry Col from Rays

This deal was made on May 15th, so including Panik in the deal wasn't too difficult, but since the deal he has hit very well. I have to say I was reluctant to give up Bruce, as I needed his power, and coincidentally he went on to hit 3-4 home runs after I dealt him. That said, the trade has worked out very well for me, even with Werth going down with an injury. Panik has been a real surprise as he is hitting for average and some power, and Norris was an easy upgrade over McKenry.

We all know how Goldy has performed this year. He is probably the best fantasy hitter in the game right now, but Mike Trout and Bryce Harper certainly have their supporters. I got the closer I needed in Jansen, but need another one to compete.

That brings me to another trade I made.

I reached out to another owner in the league who has some cheap assets, including a very cheap $1 A.J. Ramos. Ramos is in the last year of his contract, so while he has plenty of value, he can't keep him for next season. Cheap closers usually bring back at least one or two keepers in this league. This owner is about 30 points out of 5th place (in the money) and about 45-50 points out of first. When I emailed him, I asked if Ramos was available, and he said "everyone is available". I took that as "hey, I'm ready to bail."

But that was not the case. I had offered my $5 S2 Maikel Franco in a bail offer. He responded that he wasn't bailing and "what else are you adding to Franco for Ramos?" My response was "I assumed you were bailing. and am looking for more than Ramos for Franco." He came back saying we weren't on the same page, which I agreed. I am sure this happens in most keeper leagues. Each owner feels their asset deserves more in a trade, and then subsequent negotiations either results in a trade or not.

The day after we traded these emails, I asked "what do you want for Ramos?" Simple question. Just wanted to guage what he wanted and whether I was willing to meet his asking price. He responded "Goldschmidt or Zimmermann." I wasn't trading Goldy, but was willing to deal Zimmermann. You see, Zimm is one of my few good starting pitchers, but I really needed another closer.

What surprised me about his asking price is that Zimmermann is also in the last year of his contract, and at $19, he is at value. Ramos is severely undervalued at $1. In this 4 x 4 league, good closers for for $30 or more. If Ramos was in the draft, he probably would have gone for around $25, which is what teammate Steve Cishek went for in our March auction.

So, i responded to his ask "Zimmermann for Ramos?". He responded "put it on the site, and I will think about it." He decided to accept the offer, so I got my second closer.

My point in writing about the last trade is that when you are out of the money by 30 points in a keeper league, you should bail. But, not every owner likes to bail and go through a rebuild. I have found that bailing and rebuilding has been a very successful strategy in my many years of playing in keeper leagues. I enjoy bailing because there is always a trade to be made, for cheap assets, minor league prospects or future farm picks.

So, my team is currently in 3rd place, 1.5 three points out of second and 9.5 points out of first place. I think I can compete for the title this season, but it won't be easy, and there will be more trades made.

I wrote this as an exercise in bail trades, playing for this year, how the trade negotiations can go, and knowing when to bail. Hope this is helpful.