Beyond our fantasy baseball content, be sure to check out our award-winning slate of Fantasy Baseball Tools as you prepare for your draft this season. From our Cheat Sheet Creator – which allows you to combine rankings from 100+ experts into one cheat sheet – to our Draft Assistant – that optimizes your picks with expert advice – we’ve got you covered this fantasy baseball draft season.

“A boat’s a boat, but a mystery box could be anything. It could even be a boat. You know how much we’ve wanted one of those.”

Even though I haven’t watched Family Guy in years, those words from Peter Griffin — along with his ill-fated decision to take the box — always runs through my head when discussing trades involving prospects in keeper and dynasty leagues. Sometimes we all get so blinded by the sweet nectar of untapped potential that we forget the risks.

That toolsy 19-year-old might blossom into an All-Star four or five years down the road. You know who else who could be a star for your fantasy squad? A current one.

Sometimes a grand prize looms inside the mystery box. Other times, prospects never return any value. This is not a call to sell the whole farm; developing a strong crop of young talent is paramount to long-term dynasty success. Winning managers, however, must know when to exchange some of those risky youngsters for immediate help. Let’s examine the keys to optimizing the value of prospects in keeper and dynasty trades.

Get expert advice during your draft with our fantasy baseball draft software

Consider Your Team and League

The beginning of a rebuild is not the time to trade prospects for veterans. It’s also unwise to unload the fruits of that long-term planning the second your team is once again semi-competitive.

Before proceeding, keep your team’s situation in mind. When a championship is in sight, it’s time to dangle some youth on the trading block.

Of course, there are far more variables that one must weigh. Beyond your scoring system, some factors include:

• Do you have a farm system beyond the big league roster? If so, how many players can it hold?
• How many rounds is your annual prospect/restocking draft? Do you have to cut down your roster beforehand?
• Are there salaries/yearly limits to keepers, or can you protect someone forever?
• What are the league’s rookie eligibility rules? Some allow more leeway beyond the MLB’s rookie definitions of 130 at-bats for a hitter and 50 innings or a pitcher.
• Can you freely call up/send down prospects as long as they’re still eligible, or do they need to stay up once they’re called up?

It’s imperative to weigh all of your league’s settings. The shallower the league, the easier it is to find talent. That can often come in the way of post-hype sleepers who are cut after tumultuous starts to their careers. In these circumstances, a B-level prospect is expendable. In fact, it’s probably wise to shop them while their allure remains intact.

The math, of course, would change in a 16-team league with an expansive farm system and a five-round offseason draft. And in a league with an uncapped farm system, don’t try to collect them all unless you can exchange some for big-league upgrades.

Find the Sellers/Prospect Hounds

It’s virtually impossible to map out a prospect’s entire career before his MLB debut. As a result, there are often wide gaps in perceived value from manager to manager.

Opinions of particular players vary, but an astute dynasty manager can often identify trends in the competition’s overall prospect philosophy. Some league-mates view them as expendable lottery tickets. Others love hoarding prospects to the point where rebuilding becomes a way of life rather than a necessary short-term project.

Knowing where everyone else stands will make it easier to find the right trading partners. It also helps to pinpoint any homers liable to overpay for minor leaguers from their favorite team.

Sell at the Right Time

A 25-year-old batter tearing up Triple-A’s notoriously hitter-friendly Pacific Coast League may never hit his weight in the majors. That 20-year-old firing gas past overmatched Single-A opposition will eventually need to locate his secondary offerings.

Not everyone reaches The Show, and plenty who do never amount to much. That means many prospects have already peaked in terms of their fantasy value. Gamers tend to hold on tight to any prospect working his way up the organizational hierarchy, but a clear-headed one will move risers before some warning flags rise to the surface.

In some cases, a prospect’s big-league promotion might be the perfect time to strike. Perhaps even an unsustainably strong start will propel the helium out of proportion. The key is often reacting before they have a chance to depreciate their value with early growing pains.

There’s No Such Thing as a Pitching Prospect

This saying is admittedly a bit harsh. Clayton Kershaw, Gerrit Cole, and Stephen Strasburg were once top pitching prospects. Some young hurlers pan out, but the success rate is uncomfortably low. Even if they perform well on the grand stage, the added injury risk makes them highly volatile commodities.

Before assuming you have the next ace in tow, let’s take a sobering look at MLB.com’s top pitching prospects from 2016.

 
As of May 2020, 10 of these pitchers have undergone Tommy John surgery. Some keeper and dynasty managers might have lost patience with Giolito and Glasnow by the time they finally turned a corner in 2019. The only other success story, Hader, found his niche in the bullpen.

When in doubt, trade the pitcher instead of a hitter. For that matter, draft or add more position players in the first place. While plenty also flamed out, MLB.com’s overall top 40 in 2016 also included Yoan Moncada, Gleyber Torres, Aaron Judge, Cody Bellinger, Rafael Devers, Ozzie Albies, Austin Meadows, and Josh Bell. To build a winning pitching staff, tackle the waiver wire aggressively and acquire reclamation projections like Giolito at their value’s nadir.

Build Depth, and Keep Some Blue Chippers

For a good blueprint to optimally maneuvering prospects as a contender, consider the Dodgers. They’ve leveraged their deep farm to land Manny Machado and Yu Darvish in midseason deals. They snagged Mookie Betts before 2020 … all without sacrificing one of their top-tier prospects.

Team president Andrew Friedman has shown a willingness to address needs and chase available stars, but he refused to part with Bellinger, Corey Seager, and Walker Buehler. This has resulted in a loaded roster led by home-grown cornerstones.

In a dynasty league without expiring contracts, you’d need to trade your top prospect to acquire a superstar hitter in his prime a la Betts. For that type of MVP-level stud in his prime, it’d be a no-brainer decision for any minor leaguer short of a Ronald Acuna Jr-level phenom.

By building a strong farm system, fantasy managers can exude some selectivity. Only sell your blue-chip hitting prospect if you can land a young enough stud in return. Don’t worry, the other guys will draw interest. Some people can be optimistic to a fault, which leads to them mistaking a mid-tier prospect’s floor as “solid regular” when it’s really “Triple-A depth piece.”

With strong drafting and careful planning, a fantasy manager can build a championship contender without entirely jeopardizing the future.

2020 Draft Kit: View printable cheat sheets, sleepers & mistakes to avoid

Subscribe: Apple Podcasts | Google Play | SoundCloud | Stitcher | TuneIn

Andrew Gould is a featured writer at FantasyPros. For more from Andrew, check out his archive and follow him @andrewgould4.