One Big Question: Is it smart to use Chandler Shepherd as a starter?

Welcome back to the One Big Question series here at Over The Monster. For those who weren’t around for last year’s series or simply forgot what it entails — there’s a lot going on in the world today, so don’t be ashamed! — here’s a brief reminder. Every day, Monday through Friday, for the next eight weeks we’ll profile a new member of Red Sox 40-man roster. Rather than simply going through a simple profile of their overall game and what they offer the team, we’ll focus on the one question that could very well dictate how their season will go in 2018. In order to keep the order objective and avoid side conversations like ranking the players on the roster, we’ll go straight down the roster in alphabetical order by position. In other words, we’ll go by how things are ordered here. If you miss any editions or would like to look back on some of last year’s, you can see all of them here. Today, we’re looking at Chandler Shepherd.

The Question: Is moving Chandler Shepherd to the rotation a smart move for the Red Sox?

With J.D. Martinez in tow, I think it’s now fair to say that Boston’s bullpen is the biggest question on the roster. It was a phenomenal unit in 2017 and essentially the entire group will be returning in 2018, but there’s no guarantee for a repeat performance. There is plenty of upside, but beyond Craig Kimbrel every reliever in the bullpen has fairly significant question marks. With that in mind, it makes sense for the team to gather as much depth as possible and attack the problem with quantity. If someone doesn’t work out, they can just turn to the next guy in line and hope he does. Rinse and repeat until you get a formidable unit. Despite that theory, Boston is preparing Chandler Shepherd to work out of the rotation, potentially removing one of their depth options in the ‘pen. Is that really a good idea?

Jasen Vinlove-USA TODAY Sports

To say that Shepherd isn’t taking the typical pat for a pitcher would be an understatement. The righty has been pitching primarily out of the bullpen since he started college at the University of Kentucky, though he did make some starts back then. Since being drafted by Boston in 2014, he’s made exactly three starts with the organization and never more than one per season. Then, all of a sudden, he pitched as a starter in the Mexican Winter League over this offseason and the reports came back relatively positive. Now, the team plans to continue that developmental plan over the spring.

Usually, it always makes sense to err towards developing someone as a starter rather than a reliever, but this could be a special case where Boston could be trying to get too cute. The biggest potential downside in my eyes is that they are simply wasting time. Presumably, there’s a reason Shepherd’s coaches since college have had him throwing out of the bullpen, and while pitchers grow it’s really rare to see this kind of late-in-the-game developing. It’s true that they could always go back and move him back to the bullpen, but one could argue that with all of the questions with Boston’s bullpen it makes more sense to get Shepherd as much preparation as possible to help in that role and give him the best chance to help as early in the year as possible.

That being said, there are plenty of potential positives here, too, and the more you look into it the more it makes sense from a Red Sox perspective. The biggest thing about this is that Shepherd physically should be able to make this jump. He has a starters frame, listed at 6’2” and 210 pounds, and should be able to make it through a full season in this role. His delivery has also improved over the years and become more repeatable and clean. Most importantly, he has a repertoire that can stick in the rotation with three average pitches in his fastball, changeup and slider.

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Photo by Hunter Martin/Getty Images

Furthermore, while this could potentially take him out of the running to help the bullpen at the start of the year, that’s no guarantee and if/when he could help the bullpen he could be more valuable. While Shepherd was good enough to merit Rule 5 protection, this is not a pitcher with a huge ceiling or a future as a closer. If he doesn’t make it as a starter, at the very least he could be adding a little more versatility as someone who could pitch multiple innings at a time. In this era of baseball in which teams are pulling starters earlier than ever, having someone that could go two or three frames in relief every time out is a huge asset that is only gaining value with each passing season. Plus, of course, there is the best case scenario in which it does work and Shepherd does turn into a viable back-of-the-rotation pitcher. I may not bet on it, but there’s no doubt this possibility is much more valuable for the team and for Shepherd than his likely ceiling as a reliever.

At the end of the day, I think it’s hard to argue against this being positive. While it was a total shock when I first heard that he was starting in Mexico and the plan was for him to keep starting in the spring, it makes sense the more you think about it. It’s easier to move your workload down than up — it’s the same logic behind Brian Johnson starting camp with a starter’s workload — and with Shepherd in particular he’s someone who could stand to gain plenty of value as a multi-inning arm. I would bet against the righty putting it together and sticking as a starter in the long-term, but he does have to tools to make it possible. Why not take a shot?