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The Bailey Project: How Andrew Bailey Can Improve the Red Sox Pitching Staff

The Red Sox new pitching guru can help Brayan Bello, Lucas Giolito, and more.

MLB: Game Two-New York Yankees at Boston Red Sox Eric Canha-USA TODAY Sports

Towards the beginning of the offseason, Red Sox fans had their sights set on the top shelf of the free agent pitching class. While some of the class remains unsigned, it appears unlikely they’ll wind up in Boston, leaving us with the cards we were dealt over the past several years. If you’ve been following along over said years, you’re likely of the opinion that those cards aren’t good enough. The odds would say you’re correct. Fortunately, athletes are human beings who have the capacity for improvement.

That’s where new pitching coach Andrew Bailey comes in. He’s spent the past several years with the San Francisco Giants, turning around several pitchers’ careers. He’s not some super nerd who’s going to tell his guys they need to spin the ball 200 rpm faster or get 3.217 more inches of horizontal movement. He’s a former pitcher with a clear philosophy about pitching: Find what you do well, and do it often.

Easy to say, harder to do, but Bailey managed to get the most out of his staff in San Francisco. Take, for example, Logan Webb, a young pitcher who struggled in his first two Major League seasons. Webb didn’t have overpowering stuff or pristine command. His fastball topped out at 94, his walk rate near 10%. He did, however, manage to generate a ton of ground balls with his sinker and changeup combination. Naturally, Bailey had Webb ditch his terrible four-seamer, drop his release point slightly, and start throwing a ton of sinkers and changeups. Hitters today know that Webb will be up on the mound chucking bowling balls at them, and he still managed to lead the league in ground ball rate.

Webb isn’t the only pitcher who improved under Bailey. Kevin Gausman, Alex Wood, Jacob Junis, and Anthony DeSclafani all made strides, among others. They even had a rookie, Keaton Winn, throw solid innings while throwing 55% splitters. I can’t explain why that worked for him, but it doesn’t matter. The only thing that matters is that it worked. So, while the Red Sox pitching staff might have issues, that doesn’t mean it’s a lost cause. Here’s a look at what Bailey might do with some of the Red Sox arms in 2024.

Brayan Bello

Since arriving in the Majors, Brayan Bello has been good, but not great. If he wants to become great, he’ll have to find a way to get lefties out. I’ve already offered one suggestion this offseason, but there are other avenues as well. Bello is successful against righties on the back of his sinker and changeup. That brings us right back to Logan Webb. Take a look at how he attacks lefties.

Ignore the plots on the right; Bello’s approach against right-handers is just fine, save for improving his slider. Against lefties, rather than adding a cutter, or tweaking his fastball, why not copy Logan Webb, and throw your two best pitches at the front hip of lefties? It can be a difficult pitch to execute, but it’s effective when done correctly. Bello has had two decent seasons on the back of his sinker and changeup, so why not throw them?

Lucas Giolito

Another way Bailey has helped several of his pitchers is by tweaking their mechanics. Take a look at Kevin Gausman before and after getting to San Francisco.

As you can see, Gausman comes set at a different position and strides further down the mound on his release. Not only did that add velocity to his pitches, but increased his extension as well. Gausman lives and dies with his fastballs, and a more athletic delivery helped accentuate those pitches.

Over time, Lucas Giolito has seen his delivery change. His release point has fallen, and his velocity and vertical movement have dropped with it. And although his extension has increased, his mechanics look less efficient overall. Here’s a look.



Before Giolito even begins to move we can see some differences. With Cleveland, his feet are closer together, and his toes are pointed slightly outwards rather than straight toward home plate. His shoulders are also further back at the set position.

If you start to scrub through the videos you can see that at their lowest, his hands are in very similar positions, but as he loads, his hands and front leg come up much higher than in the past. He also has a more pronounced bend in his wrist at the top of his delivery, and his shoulders look a little more tense. As he begins his stride to the plate, his left foot comes back, nearly touching his right knee in his 2023 delivery.

That’s a lot of mumbo jumbo, who cares how his mechanics have changed? I won’t pretend to be a pitching coach. Well, that’s exactly what I’m doing. But I won’t pretend to be a good one. Still, mechanics certainly aren’t my area of expertise. That being said, to me, this looks a lot less efficient, which could explain the decrease in velocity. An easy way to evaluate someone based on “the eye test” is by looking at how easy things look. Giolito’s new delivery looks more effortful, and he’s had worse results. I expect Andrew Bailey to help the righty tighten things up and use a smoother, more athletic delivery.

Josh Winckowski

Early reports have stated that Josh Winckowski is reporting to camp and preparing as a starter. I’m not reading into that too much, as it’s much easier to become a reliever when stretched out to start than it is to go the other way. Right now, it seems like a three, maybe four-man race for one spot in the rotation, and Winckowski will likely find himself in the bullpen. Given that Winckowski will be pitching out of the pen, he can probably get away with throwing just two pitches.

In 2023, Winckowski had a reverse split, with righties hitting him much better than lefties. Against lefties, he used his entire arsenal (sinker, cutter, slider, changeup). Against righties, he cut out the changeup and used his other three pitchers.

Against same-handed hitters, his sinker and cutter each did a great job earning strikes, but his slider was hit hard. To me, the issue is his pitch separation.

As you can see, it’s very difficult to differentiate between his slider and cutter. Some of that has to do with how the pitches are classified, but even still, the two pitches are very similar. His slider is just a slightly slower version of his cutter and that’s causing problems.

It can be difficult to throw multiple breaking balls without them blending. Sometimes a pitcher who throws a cutter might start to put some cut on their four-seamer out of habit, which can be detrimental to their arsenal. As the season went on, Winckowski lost some of the lift on his cutter, bringing it even closer to the slider. Here, the fix is easy: get rid of one of the pitches. I would keep the cutter, as it’s useful against both sides of the plate. You can throw it down and away from righties, and up and in against lefties. After that, it’s just getting the sinker inside more often. Sinkers in, cutters away. Kind of like 2021 Garrett Whitlock.

Again, I’m not a pitching coach, and Andrew Bailey knows better than me what adjustments to make. These are just a few ideas to illustrate just how small changes can make a big difference.