Winning in fantasy football is all about knowledge and luck. You need to know your stuff but you also need to get lucky. If you do this long enough, you’ll have a person who drafts a kicker (and/or defense) in the 7th round, starts guys on a bye, and still ends up making the playoffs over you. It’s frustrating but these things happen. While you can’t really control that, there are actions you can take in other ways to improve yourself. One of those is draft pick strategy when trading.
When I was brand new to fantasy football, the main league I was in allowed us to trade draft picks 2 years ahead. I noticed that one owner would always have a lot of extra picks. I noticed he was always “getting lucky” in drafts and doing a lot of trading on draft day. He was doing something fairly simple that can really help in the long term. If a trade was even, he’d ask for a late pick (or round upgrade). If he was giving a pick, he’d ask for a late one back. It occurred to me that he wasn’t “getting lucky”. He was making sure he always had a full draft and while upgrading his team, he was giving himself shots for sleepers in the draft. You don’t find sleepers in the first or second rounds. You find them in later rounds. If I’m trading away early picks and I feel my team is worth it, I am damn sure going to try to stay even with multiple picks in later rounds. Sleepers are essentially lottery tickets you take late in the draft. If you have more lottery tickets, the better shot you have of winning something.
I took this strategy a step further. I’ve said before that you should know your trading partner. You need to know their roster. You also need to know their draft pick set up. If you’re moving a guy that a team really wants, it isn’t insane to ask for a draft pick (or two) in a later round that they can’t use anyways. Example: you keep 12 players and draft 8 rounds for a 20 man roster. This person has their 12 but they have double picks in two rounds so they won’t be using their 7th or 8th rd pick, ask for it. Not for free but when you do a deal, it’s worth a shot. It’s a lot easier to take a flier on someone at the end of the draft and hope they hit than to be short and battle the rest of the league in waivers. In my deep keeper (12 protects, 8 rounds, sound familiar?), I was able to get Karlos Williams late. He started off the 2015 season productive, fell off, but came back again in week 9 (110 yds and 2 TDs) and closed out the year with a TD in his final two games. Did he set the world on fire? Not really. Did he help me win that week 9 game and become trade bait? Absolutely. Of course, when I did trade him, I asked for a draft pick in the deal. I didn’t get him but Danny Woodhead went late in the same draft. He was a beast in PPR. He also had 9 total TDs. Pretty good for a guy who went late. There are tons of examples you can give but don’t be afraid to ask “how about you throw in a pick?”.