OTM Roundtable: How to approach an unprecedented draft

This is a very strange draft for the entire league and for the Red Sox in particular, as we’ve already discussed all week. To recap: The length of the draft has been shortened from 40 rounds to five. The bonuses are almost entirely deferred to the next two years. Bonuses for undrafted players are capped at a paltry $20,000. The Red Sox only have four selections with their second round pick being stripped as a result of their sign-stealing scheme from 2018. Scouts didn’t get to see players from the all-important March-June stretch because of the cancellation of high school and college seasons across the country. So, with all of that in mind, this week’s question of the staff was: With [everything I just mentioned], would you prefer a more conservative or aggressive approach with this draft?

Jake Kostik

I would prefer the Red Sox to be more aggressive in the draft. With only five rounds, and four picks, there’s an argument that we should play it safe because we need to hit with those five picks. Even still, I would argue that with only four picks, we have so little to lose that we may as well reach for the stars.

Following the draft, there’s a signing phase, and college seniors are going to have an incentive to sign. You may even get a few non-seniors who are willing to jump over to baseball with the unknown state of the world right now. In any case, there will be plenty of “safety” picks available later on, following the draft, but you won’t have a chance to get those aggressive picks if they go undrafted. They’ll just go to college or return to it.

Ultimately, it just comes down to luck anyway, so we may as well dream big.

Shelly Verougstraete

I would love the team to take a pretty aggressive approach when it comes to the draft. While the system has been getting better, it is still lacking many high ceiling guys. The team could, hopefully, sign some safer guys after the draft to offset some of the risk taken on during the draft.

Michael Walsh

The Red Sox should definitely take a conservative approach to this unique draft process. I’m most in favor of going after collegiate hitters with at least two or three picks. While high school players tend to have higher ceilings, they also have much lower floors. Collegiate players have proven to be much safer bets, and typically spend less time in the minors than the average high school prospect. Safe is ideal for this unprecedented draft; with only 4 picks, having multiple busts could render the draft virtually useless. Without naming prospects, my ideal draft would be to nab three collegiate hitters and a collegiate pitcher. Perhaps next year, with a full draft, a potentially reset tax, and a (somewhat) rejuvenated farm system, will be the time to go aggressive.

Mike Carlucci

The MLB draft is not a tool for immediate gain. Players selected out of college or high school are usually not ready to step in and help their team. For every John Olerud who skips the minors there are many, many Jacob deGroms or Josh Donaldsons who aren’t stars until they actually hit the majors. The aggression I’d like to see is after the four picks are made. The rest of the draft is essentially free agency with contracts capped at $20,000. The Sox have the money. Sign as many kids as possible and see what happens.

Is this a fair system for kids who are unfortunate to be draft eligible this year? No, probably not. A lot of bonuses will be fractions of what they would otherwise have been worth. But from a team perspective, offer as many max contracts as you can and see who will take a chance with the Red Sox. Dave Dombrowski promoted, traded, and otherwise emptied the farm. No reason not to try and stock up now. 2020 was a lost season with Mookie, Price, and Sale not playing for the Red Sox. Don’t throw away any help for the future.

Phil Neuffer

Matt wrote a piece on the Red Sox’s loss of a second round pick at the end of … April. Wow. That feels like it was 25 years ago. Anyway, he outlined why there’s reason to believe if the Red Sox were going to lose a second round pick, this might be the best year to do it. I think he made a compelling point (and not just because he is my editor). Of course, you could use that point to go either way on this roundtable question, but to me, it adds credence to the need for a cautious approach. With so many unknowns, and there are a lot, I really don’t want the Red Sox to be too aggressive with the draft, especially if it could cost them players from their current prospect pool in an attempt to trade up or for more picks in a draft with less certainty than ever. I’m not a draft expert by any means, and maybe the next Mookie Betts is just a trade away, but this seems like the year to roll with what they’ve got.

Keaton DeRocher

With this weird-ass draft and missing a 2nd round pick, I don’t think they should have any approach. Wing it. Don’t even think about it until you’re on the clock. The most valuable part of this draft will be the undrafted free agent signings when players can essentially pick the team they want vs being drafted. Use the lure of being the Boston Red Sox and cash in on the post-draft signees and have a ball during the actual draft, like draft 4 catchers and make them race to majors just for funsies.

Bryan Joiner

I think the Red Sox need to take a conversative approach to this draft less because of the situation in the world and around the league than because they have basically telegraphed their intention to methodically rebuild the farm system and cannot hurt themselves by starting slow. I understand there’s huge upside to be had in injured or less heralded players, but I also know that the inherent value risk works better when you’re already sitting on a pile of found money. A few years of the slow approach and you can step on the gas again; if you swing and miss now at a big target, you’ve got even less to show for this season than you do right now, when you’ve got nothing except trading your best player in decades. Fun! All of us are here for the long haul, so if we must begin, let’s not crash in the first 10 miles.

Jake Devereaux

The Red Sox pick 17th overall this year, which is a better draft position than they typically have over the past 20 or so seasons. A good draft slot coupled with the lack of high upside prospects in the system leads me to think the team should shoot for the highest upside players available. With your first selection you don’t want to take a guy that is only upside and possesses massive risk, however, you don’t typically have to. The guys in the top 20 picks in any given draft typically have such a high talent level that they have a relatively high floor compared to the later picks. I would lean heavily towards ceiling with this pick even if that means taking a prep arm or prep bat that will take longer to develop. With the round three, four, and five selections, as well as whoever they sign for $20,000, I would lean heavily towards upside as well. I’m not sure that this system really benefits that much from guys with a low ceiling, we have a lot of those players already, let’s try and hit some home runs.

Matt Collins

This was actually my second attempt at a question this week for reasons I won’t get into here, but when I asked I kind of assumed everyone was going to say aggressive. But you know what they say about assuming. Sometimes you’re wrong. I was prepared to take the devil’s advocate side and argue for being conservative, which I do think is a valid position for the reasons outlined by others above. In reality, though, I think aggressive is the right approach. Take the upside and run with it. For one thing, there are very few “sure things” in any draft, and they will be long gone by 17, so the best case from a conservative approach is really just a medium floor, not a high one.

More importantly, I think the Red Sox farm system is a little underrated in terms of solid depth. They aren’t one of the bottom systems in the league because they lack solid players. What they lack is top-end talent. Mick Abel is the guy I most want, but really I think they should be swinging for the fences with whoever is available (my sense is that Abel will not be there at 17) to try and add to the top of their system rather than worrying about the middle of it.