The Red Sox May Have To Trade Prospects At The Deadline, Whether They Want To Or Not

Let’s nerd it up a little bit and talk about the Rule 5 Draft.

For those of you who have heard of the draft before but have never quite understood what it is (which is just about everyone), the Rule 5 Draft is designed to prevent teams from hoarding minor leaguers who might otherwise have the ability to crack the big league roster in another organization. The foundational rules of the draft are pretty simple. After signing an amateur player (either via the draft or international free agency) a team then has either four or five years (depending on the age of the player when he signed) to assign that player to the 40-man MLB roster. Any player who has been in the minors for four or five years who is not protected on their organization’s 40-man roster is then eligible for the Rule 5 Draft and can be selected by another organization. It gets a little more complicated after that, and there are scenarios whereby a player selected in the draft can be subsequently returned to his original team, but we don’t need to get into that stuff right now.

The Rule 5 Draft is rarely very impactful, owing to the simple fact that any player who hasn’t made a 40-man roster after four or five years in the minors probably isn’t very good. In fact, in last year’s draft (which only consists of a single round) only 15 total players were selected. That means that half the teams in the Major League Baseball took a look at the entire pool of Rule 5 eligible players and said “meh, we’re good.”

But there was something curious about last year’s Rule 5 draft with respect to the team we’re here to talk about. Of the 15 players selected last year, two THREE(!) of them were property of the Boston Red Sox: Thaddeus Ward, a pitcher who maintained a 2.43 ERA over seven starts with AA Portland, Noah Song, a pitcher who had been drafted by the Sox in 2019 and who subsequently spent several years in the Navy, and AJ Politi, a AA reliever who ended up getting sent back to the Sox. Song was the eleventh payer picked, snagged by the Phillies; Ward was the first overall pick by the Washington Nationals.

How did it come to pass that, of just 15 players selected in the draft, two three of them came from the Sox? Well, it’s something of a natural byproduct of Chaim Bloom’s team-building strategy. Since taking the reins on Jersey Street in late 2019, Bloom has been nothing if not a prospect hoarder. In his four years on the job, he has dealt away just two semi-notable minor leaguers: there was the 2021 deadline deal in which he sent Aldo Ramirez (then the team’s 19th-ranked prospect according to SoxProspects.com) to the Nats for Kyle Schwarber, and there was last year’s deal in which he sent post-prospect Jay Groome to San Diego for Eric Hosmer.

Bloom has held onto to just about every other prospect or fringe-prospect he could get his hands on, with the result of this being that, when the Rule 5 Draft came around last year, the Sox had a glut of mid-level prospect types in the upper minors who weren’t ready/good enough to contribute to the big league team, but who would be eligible for the draft if not added to the 40-man. Ultimately, Bloom elected to protect Ceddanne Rafaela, David Hamilton, Brandon Walter, Chris Murphey, and Wilyer Abreu. Ward and Song were left unprotect and went on their way.

Okay, so given that the Rule V draft isn’t held until December, why are we talking about this now? Well, that’s because the Sox are going to face a similar glut this offseason, and Chaim Bloom now has one week to do something about it.

Sixty-eight total Red Sox minor leaguers will be eligible for the 2023 Rule 5 Draft if they are not put on the 40-man roster beforehand. The vast majority of them are players you have never heard of and will never hear of. But there are probably 15-20 players of that 68 who have some prospect value and would potentially be picked by another team if left unprotected. Let’s go ahead and try to guess who those might be, and rank them by prospect status, according to Soxprospects.com:

1. Shane Drohan, #6 Red Sox prospect
2. Luis Peralas, 7
3. Wikelman Gonzalez, 9
4. Brainer Bonaci, 12
5. Eddinson Paulino, 17
6. Allan Castro, 24
7. Ryan Fernandez, 26
8. Mathew Lugo, 35
9. Bradley Blalock, 37
10. Stephen Scott, 38
11. Angel Bastardo, 40
12. Christian Koss, 43
13. AJ Politi, 44
14. Chih-Jung Liu, 52
15. Ryan Zeferjahn, 54
16. Grant Gambrell, 55
17. Jose Ramirez, 57

Now we have to clarify something further: the Red Sox will be able to leave a lot of these guys unprotected without fear of losing them in the draft. That’s because one of those “more complicated” rules I glossed over above stipulates that, when a team selects a player in the Rule 5 Draft, they then need to place that player on their 26-man roster and keep him there for the subsequent MLB season. So with respect to the list above, no one is going to take Allan Castro, for example, as he’s a 20-year-old who has yet to advance above single-A. But the Red Sox will need to protect any players on the above list who are both (a) potential big leaguers the Sox like, and (b) either close enough to the big leagues that they could be selected by another team, or promising enough that a team would try to stash them on the 26-man roster even if they aren’t truly ready.

There are three absolute locks that fit that profile, three guys who, if the Sox don’t put them on the 40-man roster, will definitely be picked by another team: Shane Drohan, Luis Perales, and Wikelman Gonzalez, who are the top three pitching prospects in the entire organization. Beyond those three, Brainer Bonaci, Eddinson Paulino, Ryan Fernandez, Matthew Lugo, Bradley Blalock, Angel Bastardo, AJ Politi, Chih-Jung Liu, and Ryan Zeferjahn all fit the profile of potentially valuable minor leaguers who could be picked by another team. That’s 12 players that the Red Sox have to at least consider adding to the 40-man roster, lest they lose them for nothing. And there’s where next week’s trade deadline comes into play.

With the trade deadline now almost exactly a week away, the Red Sox have yet to commit to either buying or selling. In fact, they’ve stated publicly that they’re essentially seeing how the big league team does over the next week before deciding what tack to take. But with respect to the Rule 5 Draft, they really don’t have a choice. The Sox will likely want to protect at least four players, if not five-to-six. That means they need roster spots to give them, and that means they need to consider trading away any potential draftees now, lest they lose them for nothing.

Maybe that tips the scales for Bloom and makes the Red Sox buyers, even if they ultimately don’t want to spend that much in prospect capital; if there’s a team out there offering some middle relief help who wouldn’t mind giving it away for Brainer Bonaci, you might as well do it, because it’s going to be difficult to hold onto him anyway. Or, perhaps more likely, it’ll make the Sox both buyers and sellers, sending tough-to-protect prospects out in one deal, while bringing younger prospects who aren’t yet eligible for the Rule 5 Draft back in another.

We’ll see what the team does over the next seven days, and then we’ll argue about it. Ultimately, it probably won’t matter in the end; as I said, the Rule 5 Draft is rarely that impactful. But it always could be impactful (hello, Garrett Whitlock!), so Bloom and the Red Sox need to be careful.