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OTM Mailbag: Looking into the near-future for pitching prospects

And a look at some other potential transactions.

Boston Red Sox v Baltimore Orioles Photo by Rob Carr/Getty Images

It’s been a little bit since we’ve done a mailbag, partially due to me not having the kind of time on the weekends over the last couple of weeks that I had previously and partially because of a lack of questions. But we’re back in the middle of the week now and I’ll try to get back to these being regular. For this edition, we’re looking at a couple of pitching prospects we’ve already seen in the majors, and a few other near-future type questions.

Steve via Twitter asks

What will Garret Whitlock’s role be by the All-Star break?

This is one of the most fascinating questions for the Red Sox over the next couple of months, in my opinion. Despite the hot streak we’re seeing right now, I do expect things to even out overall on this roster and for them to get back to something resembling a .500 team, give or take a few wins in either direction. But while it’s too early to have had my mind changed on most things, Whitlock has been the exception. His stuff has stood out since the spring and he’s already making waves with his first couple of appearances in the regular season.

His future both short-term, as in the rest of this season, and long-term, 2022 and beyond, is one that I can see going in a number of directions. I would assume they want to get him into the rotation for the long-term, but we’ve seen pitchers who project as a back-end starter have success in the bullpen before and be kept in that role. It’s not out of the question that happens for Whitlock, though I’m also not really going to make any impressions like that this early in the year.

As for the question here, on the podcast a couple of weeks ago I mentioned that I could see Whitlock entering the rotation by the second half of the year due both to his own performance and injury/poor performance from the starters in front of him. I think I was off-base there, though. (Shocking, I know.) Whitlock is coming off Tommy John surgery and playing in the majors sooner than he would had it not been for the Rule 5 Draft. I don’t think they’re going to put him into that kind of workload this year.

I do, however, think we’ll see him getting high-leverage spots. I don’t see him leapfrogging Matt Barnes or Adam Ottavino, but there are a lot of question marks beyond that and it’s not at all out of the question Whitlock gets himself into that equation. And if he succeeds there, well that question about the longer term future could become interesting.

Boston Red Sox Spring Training Photo by Billie Weiss/Boston Red Sox/Getty Images

The_surfing_guy via Twitter asks

If we’re “in it” at trade deadline, does ownership go all in with this group?

All of this depends on the definitions we’re using for “in it” as well as “all in.” If the Red Sox are four games out of the wildcard, I suppose that’s in it but I don’t think that means we’ll see them taking on massive salary for a run in 2021. But if they have the best record in baseball, I can see it. So I guess to answer the question vaguely first, there is a scenario in which the owners will do what needs to be done to make a run in October. We’ve seen them do it before, and while I stand by my criticism of their financial decisions over the last couple of years I’ve also consistently mentioned that I do believe they’ll get back to spending again.

The interesting equation to work out here is what exactly would count as “in it.” Unfortunately I don’t think I have an interesting answer to that question. I see it as the definition of porn type scenario where it’s just, I know it when I see it. I don’t necessarily expect them to be in that position, but if they defy my expectations and it seems like they have a legitimate shot at a run in October by the time July rolls around, I do think they’ll be willing to make the big move to put them over the top, provided it’s out there.

Julian via email asks

Will Tanner Houck be able to pitch his way into the rotation permanently by the All-Star break?

We talked about Whitlock heading into the All-Star break, so it only makes sense we talk about the other pitching prospect we’ve seen this season. I think this one is an easier answer, though, and that is an emphatic yes. The only way I don’t think he’ll be part of the rotation picture even by Memorial Day is if there is both no injuries to the current rotation and no one pitching below expectations. I just can’t see both of those things happening simulataneously all the way into mid-July. I do think Houck can get some valuable development with his splitter in the minors, but he’s also the obvious sixth starter on the roster and there’s almost no way they won’t need him on a permanent basis by that point.

Cuyler via Twitter asks

If and when do you think a Raffy extension will happen?

I’m not aware of any hard deadline from either side about not working on anything during the season, so it’s possible something happens this year, but I wouldn’t expect it. These things tend to happen in the offseason, so I’d look for next winter for that to get done. Of course, with the CBA coming up next winter it could be a weird offseason so who knows how realistic extension talks will be. I do think an extension will happen, though. There’s no reason to believe either side doesn’t want it, and well, they have some money to spend from trading that other guy they could have extended.

The Big Man via Twitter asks

Do you hate our odds against the Dodgers in the World Series?

No, the Red Sox are definitely World Series favorites.

Thanks again for all of your questions. And again, if I didn’t get to yours look out for it in a future edition of the mailbag or on the podcast. We always appreciate more questions, so please if you have any you can either ask me on Twitter @OverTheMonster, you can leave a comment on our Facebook page, you can drop a comment down below on this post, or you can send it via email to