Is it possible for a trade to be fair in one league but not in another? I think the answer to that question is pretty obvious. If it wasn’t at first, the fact that I asked should be a dead giveaway. The answer is yes. The key here is tied to the simple fact that not all points leagues are created equal. It’s an extremely important principle that needs to be understood and one I have mentioned countless times over the years. Ronald Acuña Jr. is even more valuable in a league that does not penalize for strikeouts. Using 2019 stats as an example, with 188 strikeouts he finished as the 13th most productive (most points) hitter with 516 points. Cody Bellinger finished top of the list with 623 points. If hitters didn’t lose a point for a strikeout, Acuña would have had 704 points. That would have made him the number two hitter behind Bellinger. Just in case you didn’t think he could be more valuable. The key here is that the scoring system of the league directly affects a player’s value. That is why I put together my draft day spreadsheet that allows you to enter your league’s settings.

It’s very easy to judge a book by its cover when first being notified of a trade. On the surface trading Bryce Harper for Marcus Semien seems like a very foolish maneuver, but in 2019 that would have been a very fair deal considering Semien led the two in points. Now I’m not saying I believe I would have actually given up Harper to make this deal, but if I had, perhaps I would have finished first instead of second. Remember, it doesn’t matter how a player earns his points. A point is a point. Six walks is the same as a home run as they both total six points where walks, runs and RBIs are one point and a homer is four. The big difference is that it took six plate appearances for the walks and just one for the ding dong. Who you calling a ding dong?!

Whether or not a league is a keeper or a redraft league goes a long way in determining if a trade make sense. It’s not such a big deal to give up a big name player for the right pieces in a redraft league, especially when said big name isn’t having the best season. The fear in keeper leagues is that they will rebound in future seasons and in hindsight the trade will have been shortsighted. In my opinion, there are no players that should be off the trading block in redraft leagues. In keeper leagues however, you really need to be thinking not just about this season, but a few seasons ahead as well. Anyone that has had Vladimir Guerrero Jr. since he was a rookie or in the minors that traded him last year better have gotten 120 cents on the dollar. Did he have a blockbuster 2020? No. Should that have scared you off? No. He only turned 22 this past March.

Trades in keeper leagues are also subject to the keeper rules. If you can only keep five players and already have five strong keepers, it limits the value of receiving a keeper quality player in a trade to some extent. If you are playing for the current year then I’m sure it make sense. Trade away some young, unproven talent for aging stars. Either way, it also sets you up for the option to trade two keeper level players for one keeper that’s better individually than the two you’re trading away. Something like Corey Seager and Rafael Devers for Mike Trout.

However, if I’m in a league that allows trading draft picks, I always try and move my extra keepers for draft picks. Trading draft picks can be a powerful bargaining chip. Just keep in mind that if your league allows you to keep five players, the the first round is really the sixth round. It’s important to point that out during negotiations to downplay the value of the first round pick you are trying to secure. Ideally, the top 60 players will be off the board (kept) at the start of your draft in a 12-team league. Although there will be teams that have more than five keepers that will be forced to throw the extras back, making them available on draft day. I often try and target draft pick trades with teams that look like they will have an early first round pick.

It wasn’t until recent seasons that I began to trade away my draft picks. I used to cling to them for dear life, but then I did some research. I looked back at the last ten or so seasons to see how valuable my first round pick was in relation to my team as a whole. What I found was that first round pick rarely ever made a huge deal for any team in the league. With 60 players off the board before the draft even begins, the “sure things” are gone.

In leagues formerly known as “auction” leagues, it is vital to factor in the player’s expected salary. During Cody Bellinger’s rookie season I snagged him towards the end of our auction for $1. Mike Trout went for $43. Which one of those players do you think was more valuable going into the following season? That’s a trick question. It was Bellinger and it wasn’t even close. That season I was in strong contention for the title so I traded Bellinger away for Trout ($43) and Clayton Kershaw ($48). From a 10,000 foot view that trade seems awfully lopsided, but when you factor in each players’ salary, it’s a perfectly fair deal. Like Billy Jean said “fair is fair“.

A common rule of thumb many will preach is that you always want to get the best player in the deal. That is something I have abided by with every trade I have made. If it’s a 2 for 1 or 2 for 3 type deal I am always the team giving up more players. The previous anecdote with the $1 Bellinger doesn’t count because salaries change the dynamics of the trade.

When calculating a potential trade you need to consider your positional needs. Why trade for Xander Bogaerts when you already have Corey Seager and Francisco Lindor? If you’d have to sit one of them to start Bogaerts then you’re not really making your starting lineup much better are you. So instead of targeting Bogaerts, why not aim for Manny Machado, Nolan Arenado or Rafael Devers to replace Colin Moran at 3B. The goal should always be to improve your starting lineup. Points on the bench are as useless as tits on a bull.

Last week I made the following trade in my primary head-to-head points league which I’ve been in for twenty years. I traded away Gerrit Cole and got back Walker Buehler, Juan Soto and Logan Gilbert. Without any of the league details, it seems like a steal. The most important thing to know is that the scoring system in this league is severely skewed towards starting pitchers. To put that into perspective, here are the top hitters and pitchers points totals over the last six years.

2020: Freddie Freeman 262 points, Shane Bieber 381
2019: Cody Bellinger 623 points, Justin Verlander 902 (there were 9 pitchers with more than 623 points)
2018: Jose Ramirez 637 points, Max Scherzer 843 (11 pitchers with more than 637)
2017: Joey Votto 619, Corey Kluber 852 (11 pitchers with more than 619 points)
2016: Mookie Betts 620, Max Scherzer 833 (14 pitchers with more than 620 points)
2015: Bryce Harper 573, Jake Arrieta 927 (16 pitchers with more than 573 points)

The trend continues every year.

Based on my draft day spreadsheet, Gerrit Cole was the number one ranked player in the league with a projected points total of 740. Guess who’s the second ranked player? That’s right, Juan Soto with a projection of 580 points. Based on my projections there are eight pitchers ahead of Soto. Buehler is not one of them. He’s the tenth ranked pitcher and 35th overall player with 563 projected points. So I trade the best player in the league for the second and 35th best players. This trade also violates my “get the best player in the trade” policy. So why’d I do it? We can keep ten players (plus four minor leaguers) forever without any sort of penalty. The determining factor here was the age of the players involved. Cole is 30 years old, while Soto is 22, Buehler is 26 and Gilbert is 23. Giving up Cole was a tough pill to swallow, especially for a lifelong Yankees fan, but this was a deal I could not pass up. Buehler is unlikely to ever be the strikeout pitcher Cole has become, but if he can be 80% of Cole, Soto shifts the balance of this deal in my favor by a fair amount. Gilbert becomes the wildcard that could really tip the scales.

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