Rebuilding in a Dynasty League

Massive dynasty leagues have become increasingly popular among fantasy baseball players in the past half decade. They tend to involve much larger rosters than standard rotisserie leagues and may or may not utilize a contract system that impacts the amount of time an person can own rights to a player.

The most-difficult question a fantasy owner must address in a dynasty league, though, does not take place on draft day. Most of the time, the mind-numbing conundrum occurs midseason when an owner must decide whether or not his or her team will buy, sell, or hold. It’s not a simple question to address, as rebuilding in a larger dynasty league isn’t generally a one-and-done deal. Those rebuilding jobs literally take two or three seasons, at the very least. Embarking on such a strategy isn’t fun, nor is it easy to do well.

As someone who is currently undergoing a massive rebuild in a 20-team dynasty league with 40-man rosters and 35 keepers per year, I wanted to offer a few pieces of advice to owners who have decided they want to sell.

(1) Be aggressive and sell early.

If you’ve decided to pull the trigger and begin the rebuilding process, the worst thing one can do is half-commit. I’m not suggesting one should engage in a complete firesale and move every big-league piece in favor of prospects, but it pays to go big and to go early. After all, if you beat everyone to the party, you can have your pick of the prospects or young players you want to target. Additionally, and perhaps most importantly, being the first one to sell allows you to avoid negotiating against people, and it places the rebuilding owner in the driver’s seat. If you adore someone like Javier Baez, the worst-case scenario for a rebuilding owner is to have the Javier Baez owner negotiating with three or four rebuilding teams. You want to corner that market.

In my current rebuilding process, I’ve made five separate deals. It’s the middle of May. While certainly aggressive, I’ve been talking to other owners who are debating on whether they want to sell, and they’re lamenting the lack of attractive prospects on the trading block. Why? Because many of those prospects that were available are now on my squad. I beat my competing owners to the punch, and now they’re wanting to sell without anything they want to buy.

(2) Target players in Double-A and Triple-A, if not in the big leagues.

Engaging in a rebuilding process is difficult. It’s even more difficult when that rebuilding process takes three or four years to come to fruition because you’re waiting on guys in A-ball to make it to The Show. Not only do those players have a higher risk of flaming out before reaching the majors, but as an owner, you’re also forced to twiddle your thumbs for a couple of years with nothing productive happening.

Targeting MLB-ready players — or at least near MLB-ready players — shortens the rebuilding process as much as possible. Again, using myself as an example, I’ve acquired guys like Jon Singleton, Oswaldo Arcia, Trevor Bauer, Rymer Liriano, Maikel Franco, Alex Meyer, Luis Sardinas, Jarrod Parker, Mike Foltynewicz, Yorman Rodriguez, and Sean Nolin (and a couple lower-level players). There’s an exceedingly-small chance all of those players panning out. However, I’m building a wide base of players who have the chance to be at least league-average players, and in a 20-team league with 40-man rosters and 35 keepers, that depth is crazy important.

Importantly, though, many of those guys listed above are expected to begin breaking into the big leagues later this year, if they haven’t already. I’m shortening my rebuilding time as much as possible by acquiring guys who should contribute as soon as next season. And going back to point number one, it wouldn’t have been possible to acquire so many Double-A and Triple-A guys if I hadn’t been aggressive and sold early.

(3) Don’t be overly concerned with “winning the trade.”

Too often, trade negotiations in fantasy leagues crumble, or don’t even get beyond the initial proposal, because each side becomes too worried about winning or losing the trade. It’s the way we’ve been conditioned to evaluate trades, and when that email is sent to the entire league that announces the trade, we naturally do not want the remaining owners to view us as incompetent or foolish. Thus, owners often become too timid to accept a trade proposal unless it’s overwhelmingly clear that they’ve “won” the deal.

And, well, that doesn’t happen all that often.

When entering trade negotiations, understand your overall goal and seek to achieve that goal, even if the other owner may slightly be getting more value. And context matters. Quite simply, if you feel a trade will ultimately improve your squad with your particular roster construction, that’s what is paramount. It’s not about winning or losing the deal in the abstract. It’s about getting your team back in contention as quickly as possible.

Overall, rebuilding in deep dynasty leagues is difficult. One must have a plan, and execute that plan. But more directly, if you’re absolutely out of contention and have no hope of climbing back into contention, it pays huge dividends to sell early and beat the crowd. Focus on those prospects close to the big leagues, and short-circuit the rebuilding process as much as possible, while the remainder of the rebuilding clubs acquire A-ball prospects later in the summer and have to wait three or four years.