Trading Keepers for Picks — Is It Worth It?

I am in a 15-team 5×5 league, with 4 keepers. Every year before the deadline, some teams try to trade their #5 keepers to other teams for picks. Then, after keepers are processed, a few will still try to make trades by giving up a keeper for multiple picks. I found myself entrenched in this situation when I traded for Clayton Kershaw this offseason.

I pick first in the draft order, with a snake format. The owner of Kershaw asked for Donaldson and my 2nd round pick, or #30 overall. I said yes in a heartbeat, despite the fact that I had Jon Lester already on my keepers. Normally I don’t like to pair two starters in my keepers, but when Lester was clearly a cut above my other options (Adam Jones, Jason Kipnis), it made sense to pair him with Kershaw and give me a huge leg up in ERA, WHIP, and strikeouts. Plus, because I still had the #1 overall pick in the draft, I could grab the best available bat to boost my offense; in this case, it’s Yoenis Cespedes.

However, the owner has had second thoughts. He has traded several players for keeper downgrades and extra picks. He now has five picks in the first two rounds. And he wants Kershaw back. He asked me if I would give back Kershaw in exchange for his two first-round picks (#13 and #15 overall), plus a fifth round pick. I immediately said no, and it opened up a discussion about the value of picks, the value of keepers, and when you should prioritize this year or your future before the season even starts.

His Argument for Picks Being Valuable

I can understand parts of where he’s coming from, but the full picture doesn’t mesh with my own beliefs and strategies. As briefly and unbiased as possible, here is what he argues.

  • He sees a lot of value in giving up one elite player for “three really good ones.”

Normally, the safe fantasy adage says that you should always seek the best player in a trade, and that implies a 3-for-1 is never a win for the guy getting 3 players. I don’t believe that adage is always true in a vacuum, and clearly my trading partner doesn’t believe it either. He says that getting several good players for one elite one makes you more likely to win.

  • After keepers have processed, who they are makes no difference at all.

The reasoning here is that before the deadline, you’re looking to get the best 4 keepers on your team. However, after that fact, and during the season, your team is simply the 25 guys you have, and regardless of who was a keeper, they’re just players on your roster now.

  • He believes top keepers are always available for trades, during all parts of the year.

He doesn’t feel that most teams lock down their top players forever and refuse to trade them. As such, placing tons of value on your #1 keeper doesn’t make sense if you can get a haul for him to help you try and win now. He thinks that later in the year, if you’re out of the championship picture, then you can simply package some good pieces for a first-round kind of guy. In other words, there are always “win now” teams who will sell their best player to a team who wants better keepers; the market is always available for whatever you desire.

  • In roto leagues, you may be better off with “two or three Quintana types” than just one Kershaw.

Some good second-tier starters are available in the draft. Chris Archer is out there, as are Hendricks and Quintana. He seems to be arguing that with my extra picks, I can use them for 2-3 SP in order to replace Kershaw. It’s true that with more innings, you usually get more strikeouts, and the more pitchers you have with good ratios, the more impact they have on your team total.

My Argument for Keepers Being Better

  • “Really good” does not come near equaling an elite player.

In this same league a few years ago, I traded Mike Trout in attempt to win the year. It didn’t work. However, at the very least, I got in return Adam Jones, Ryan Braun, Gerrit Cole, and Alexei Ramirez. Jones and Braun were both considered tier-one OF and also top-30 players at the time. Trading the #1 player for two guys at or above #30 makes more sense to me than getting back two players outside the top-70. With 15 teams and 4 keepers, that’s 60 players kept. The fact that his picks were late in the first round means I’m giving up Kershaw for the #73 and #75 players. These “good” players can’t offer me the same value per roster spot.

Yes, I’m technically gaining an extra pick in the first round. However, the type of players available are ones like Adam Jones, Jose Bautista, and Ian Kinsler. None of them project to give me more than $25 value in 2017. Kinsler is the top value of the three due to his position. Kershaw alone projects to be $45 by one source, and that’s with only 28 starts. I have to spend two roster spots on Jones and Kinsler to come near $43 in value, but Kershaw is worth more than them alone, so the extra draft pick isn’t worth it.

In comparing my return for Trout, for Kershaw it means I’d be looking at getting two top-30 players — guys like Dan Murphy ($31) and Freddie Freeman ($26), plus two smaller pieces. At least then I’d technically come out ahead, and I currently wouldn’t have to discount the value for any drops because my roster isn’t full.

  • Keepers always are a factor, even if they’re a little less important in-season.

I disagree with the fact that once the season starts, a player is just a player. There’s a reason why people haven’t been valuing Adrian Beltre as a good keeper for the last few years. Despite his great production, he’s quite old for a keeper. He may finish a season with a better value than, say, Starling Marte, but 99% of players would keep Marte over Beltre. In this league, I’m always considering who my best core four players are. I wouldn’t trade my top two players for a bunch of guys who wouldn’t qualify as keepers in the first place.

  • Teams may always be willing to trade, but not everyone is going to move elite talent.

Yes, there’s usually one crazy trade guy who loves to make deals and will move his best players over and over. However, plenty of managers are going to lock down their young, elite talent because they want that steady core — and perhaps because they simply root for those young players. Mike Trout hasn’t been traded since I moved him. Nolan Arenado has been traded once — for Kris Bryant. Bryce Harper hasn’t been traded since he reached the majors. Maybe I could find someone else, some elite name to trade half my other keepers for. But not everyone will move top-25 players, and I don’t blame them. I don’t intend to move Kershaw or Corey Seager anytime soon.

  • One elite starter is always better than two or three lower-tier guys.

I won’t spend much on this one, because to me it’s self-explanatory. Plenty of data should be available to prove this point. But let’s look at the top-2 and top-3 starters in the FA pool, by ADP: Archer, Hendricks, Porcello. Most projections have Porcello fading in ERA, and neither Hendricks nor Porcello are strikeout studs. Still, by one projection source, those three together are due for a 3.14 ERA, 1.09 WHIP, and 7 to 9 K/9. The next best SP in the pool is Quintana, so while I wouldn’t do so, if I paired him with Kershaw, I’d have a 2.69 ERA, 1.05 WHIP, and 8.9 K/9. Pairing just Archer and Hendricks gets the K/9 closer, but the gap in WHIP increases.

Besides, let’s not forget that with Kershaw, I can already pair Jon Lester with him (combined 2.55 ERA, 0.97 ERA, 9.5 K/9). That’s far more valuable than Quintana, and it frees up my next several picks to focus on hitters. Moving Kershaw almost forces me to spend one of my two new picks on another SP. I’ll sit where I’m at, thanks.


In the long run, he ended up trading his #15 pick and a sixth-round pick for Justin Verlander. Verlander had a great 2016, but he is a lot older, has an ADP of 40 on CBS (our league site), and has a far worse ERA than Kershaw over the last four years. Despite his relatively high ADP on CBS, he’s only the tenth best starter, and Kershaw is the clear number one. It doesn’t make sense for me to get only double Verlander’s price for Kershaw.

And let’s not forget that I’ve done the “win now” trade of an elite player for a huge haul. If it doesn’t bring you the championship, you’re out that great keeper. I got two decent ones in return, but at the end of the year, I’d much rather have had Trout. In this case, I’m keeping Kershaw. Your actual keepers are worth more than a pick in the draft, because anyone kept is almost always better than what’s left in the FA pool.


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Kevin Jebens

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Fantasy baseball player since 2000; winning leagues ranging from 12-team H2H to 18-team experts 5x5. Has written for various baseball blogs, including the 2013 Bleed Cubbie Blue Annual.

2 thoughts on “Trading Keepers for Picks — Is It Worth It?”

  1. I appreciate your sharing this. At this point in the preseason, these are the main types of articles that are interesting to me. It seems that he wasn’t truly arguing with you, more just trying to persuade you to take a deal that he knew was significantly to his advantage. I bet he would acknowledge that he doesn’t really believe what he was saying.

    1. Thanks for reading, Nick. You know, as hard as it is to believe to some of us, I can believe he thought his reasoning was sound. A bunch of picks in the first round may well have been to my advantage this year. Losing Kershaw would have hurt for sure, and my brain is trained to go for the best player in a deal. But there are some who often trade away players for picks, because they like having half the first round to solidify their roster for one season.

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