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Talking Mid-Season Trades: Developing a Trading Game Plan

I’ve spent a good chunk of the past three weeks in Ireland, celebrating the wedding of one of my best friends, so please excuse my absence from the interwebs during that time. I had intended to make a post when I returned about a week ago, but when a New Orleans family marries a Russian family in Ireland…well, let’s just say you need about a week of recovery time afterwards. Congratulations Ed and Kristyn.

As great as the trip was, I’m excited to be back and focusing on baseball again. We are about two weeks from the mid-point of the season, and now is a great time to take stock of where you stand and start trying to address your needs via trade (if you haven’t been already). At this point, most hot and cold starts have normalized (see: Charlie Blackmon and Edwin Encarnacion) and you should have a pretty good idea of the overall makeup of your team. It’s time to identify your strengths and figure out how best to use them to address your weaknesses.

Everyone has a different philosophy about trading. Some people stubbornly cling to their pre-draft beliefs and almost never trade. Some people just like to mix it up and trade all the time. Some will only accept a deal if it’s heavily in their favor. Others will accept a deal regardless of overall value as long as it addresses team needs. Whatever your style, before you enter into trade talks or propose or accept any deals, it’s important to have a game plan and know what kind of deals will actually help your team.

Not all trades are created equal. Giving up Dee Gordon for Josh Donaldson may seem like a steal on the surface, and you may even feel great about selling Dee high while you have the chance. But if you already have a lot of other power and you’re set at 3B, and Gordon is the only guy on your team providing any steals, then accepting that trade will probably end up doing more harm than good in the final standings.

This far into the season, you should only be entertaining offers that help you address specific categories of need, or positions at which you are weak. Trading for trading’s sake can be fun sometimes, but the ultimate goal in fantasy baseball is to win, is it not? I’m going to assume that you agree if you are still coming here reading articles this far into the season.

Now, if you are doing well so far (in the top 3-4 spots of your league, say) then you’re in the catbird’s seat. You can sit around and wait for offers to come to you, and only accept the ones that blow you away. It wouldn’t even be a bad idea to see if any struggling teams in your league have injured superstars who they’d be willing to part with for cheap because they need help now. You don’t need to make any moves, so you have the upper hand in any negotiations.

If you’re struggling, on the other hand, it’s past time to start getting proactive. Have a look at the full standings of your Roto league (or head-to-head stats page in h2h leagues) and get an idea of where you are actually good. Unless your draft was absolutely horrendous, you should have a category or two that you are at least serviceable in, and hopefully you will have a bit of an excess there from which to deal. Next, look at the standings to see which teams need help in the category that you are trying to give up. Finally, look at the categories you are struggling in and figure out which ones you can realistically make the most gains in. Keep in mind that the ratio cats (BA, OPS, ERA, WHIP) are usually the most difficult to make up ground in. If you are already 10 points back in BA from the next worst team, you might as well punt that category and try to make up ground elsewhere.

Now you have a trading game plan. 

In order to maximize your value during these trade negotiations, it’s also important to determine the marketability of each of the players providing the stats that you are trying to give up. You want to identify the most marketable player (the one that will fetch you the highest return) that you can spare without taking a big hit in the standings. If you are loaded in power and trying to trade some for pitching, you are likely to get more in return for Giancarlo Stanton than Nelson Cruz. Obviously Cruz is a bit more risky rest-of-season than Stanton, but if you are buried in the standings and need a big time pitching impact to climb back in, then that’s a risk you should take to try to get as big of an arm as possible in return.

I’ve recently made a couple moves in my big-money Roto league that I think exemplify some of these principles. Some of you may remember the draft results from this league that I wrote about pre-season. If so, then you probably already know that I need some help in a major way to climb back into the hunt. That draft started with Robinson Cano and Prince Fielder (thanks for giving him a physical, Rangers mgmt), and also included as starters Ryan Zimmerman, JJ Hardy, and Domonic Brown. Amazingly enough, however, offense hasn’t been a huge problem as some late rounders have managed to keep me afloat (Dee Gordon, Michael Brantley) and my third rounder (Jose Bautista) has been a team carrier to this point.

My pitching staff, on the other hand, has to be one of the most disastrous ever assembled. Justin Verlander, Mat Latos, Danny Salazar, Justin Masterson, Dan Haren, and Yovani Gallardo were my six starters at the onset of the season, and the only one who’s really still fantasy relevant is Latos, who just pitched his first innings of the season Saturday. It became clear that pitching stats (all of them) were what I desperately needed, and luckily enough one of our managers announced a few weeks ago that he was willing to part with a big pitcher in exchange for a good closer and something else.

We only have two RP lineup spots in this league, so having a third closer is unnecessary excess unless one of them qualifies at SP too. At this point I only had two (Rafael Soriano and Ernesto Frieri), but Sean Doolittle was a free agent and had just recorded his first save for the A’s, so I scooped him up in anticipation of trading one of the three for a new SP. Now, each of these three closers’ marketability came into play.

I viewed Soriano as the safest of the three, so I tried to move the other two first. But, as is often the case, his opinions were aligned with mine and he didn’t want Frieri (Joe Smith had gotten a couple saves in the previous weeks) or Doolittle (“you just picked him up, dude”). Clearly, Soriano was the most marketable of the three, and if I really wanted to upgrade pitching I needed to take on some risk myself by offering him up and relying on Frieri/Doolittle the rest of the way. So I offered Verlander and Soriano for his Strasburg.

And poof! Justin Verlander turned into Stephen Strasburg for very little because I was able to make up the difference from a position of excess, in this case closers. Yeah, Soriano’s probably better than Frieri, but I’ll take my chances because the impact Strasburg can make will dwarf the difference between those two closers. Oh, and that Doolittle guy? He’s been pretty darn good since.

But one pitcher wasn’t going to be enough to clean up the steaming mess left by the rotation I drafted, so it was back to the full standings to see where else I had excess from which to deal. With the aforementioned Gordon, along with Billy Hamilton and a number of other guys chipping in, I was tops in SB with a 14 steal cushion over 2nd place. In Roto leagues, winning a category by one is just as valuable as winning it by 100. So now I had a new game plan: time to turn steals into another ace pitcher.

Again, player marketability came into play. Gordon was clearly more marketable, but he was also much more valuable to me because of his position flexibility and the rest of the stats he was providing. I figured Hamilton was still fairly marketable as well, as he was a 5th round pick and still had the upside to singlehandedly carry a team in the steals category. So I tested the market for Hamilton.

The offers I got back were not terrible, but not exactly the difference-makers I was looking for either. I was looking at the likes of Ian Kennedy, Tyson Ross, Jesse Chavez, Garrett Richards, Drew Pomeranz, or Mark Buehrle in return for Billy Hamilton. So next I tested the waters for Dee.

As Dee was a top 20 player at the time, I was hoping to package him and someone else for an Ace. I put together packages for Madison Bumgarner, Adam Wainwright, Zack Grienke, and Yu Darvish or Johnny Cueto (one team has both of those guys), but got no takers. The best offers I got in return were Dallas Kuechel, Michael Wacha, or Richards and Homer Bailey. Clearly, Dee Gordon was not as marketable as I expected him to be, as people still didn’t really believe he is for real. So I decided he was more valuable to my team than as a trade chip, and I would keep him and take what I could get for Hamilton.

I ended up settling for Tyson Ross. Is he the ace I was hoping to get for one of my elite speed guys? No, of course not. But he is a good young pitcher who has been strong in his sophomore season, fairly consistent, and a reliable K producer. Moreover, he pitches in the better league, in a great home park, and in a fairly tame division, so he has a pretty safe floor.

Feel free to tear apart this deal in the comments or on twitter. On the surface, it looks like a pretty clear loss based on overall values alone. But this deal was extra valuable to me because Hamilton was doing almost nothing to help me in the standings. With a 14 steal lead, I could have still been in 2nd in the category if I hadn’t had him all year. His production in other categories is mediocre at best, and highly detrimental at worst (hello .660 OPS). Trading him for any reasonably good pitcher would have benefited me, but I got one with good current numbers, a good setup, and youth enough to still have upside for greater things.

Though these deals, a couple free agent pickups, and Latos finally returning from the DL I’ve turned a rotation of Verlander, Masterson, Roenis Elias (picked up when Salazar was DFA’d), Haren, and Gallardo into Strasburg, Latos, Ross, Phil Hughes, and Masterson, Haren, and Jake Odorizzi battling for the last spot. It may not be the most elite rotation ever, but at least it doesn’t make me want to throw things at my computer screen. And it should be good enough to let me crawl back to the middle of the pack in a number of pitching categories. All while giving up nothing but excess.

So when you’re looking to make deals at this point in the season, make sure you know what categories and positions you really need, and which ones you can easily spare. Whenever you are considering trades, you should always have a game plan. Trades that look great on the surface may actually be detrimental based on the makeup of your team as it currently stands. And sometimes, trades that don’t look so great may be just the ones your team needs to make that necessary push in the standings.

I’d love to hear about some of your experiences with mid-season trades, especially in light of your team needs and how the trade fit into them. Let us know about them in the comment section, or on Twitter at @RotoClayton. Thanks for reading, I’ll be back soon with some more Sleeping Beauties for those of you looking for help from the waiver wire instead of your leaguemates. Until next time…