Reaching for the Stars
Estero High Pitcher Josh Winckowski makes the Big Leagues in Boston
By Craig Handel
A baseball pitcher is called many things — hurler, sidewinder, moundsman, hard thrower, soft tosser, southpaw, reliever, closer.
Not a catapulter.
But that’s how Boston Red Sox and former Estero High pitcher Josh Winckowski described his pitching style in his teen years.
By altering those mechanics, his pitching improved, which led to him being drafted by the Toronto Blue Jays in 2016.
After being traded twice within a month in 2021, he went to the mound 15 times as a part-time starter last year with the Red Sox. This year the 6-foot-4, 202-pound right-hander has gone into spring training hoping to take the next step as a major-leaguer and pitcher.
“As you get older and change physically and mentally and evolve from high school to pro ball, there’s a level you need to be at competitively,” Winckowski said. “In high school, I only threw one to two pitches. Now it’s 4 1/2 to five, depending on the day. The key is evolving and working to change things over time and getting better every month, every year. Keep on working.”
Winckowski started his career at Cypress Lake High before coming to Estero as a junior.
“Word on the street was he had a pretty good arm, some control problems or he’s easy to hit,” said Gary White, who coached Winckowski at Estero.
After watching and coaching him in fall leagues, White couldn’t pinpoint it, but “something wasn’t right.”
He watched Winckowski throw from behind, took videos of him with his iPhone, then took about 50 still photos. He also showed him photos of Roger Clemens, Tim Lincecum and Corey Kluber, who ironically, now is Winckowski’s teammate.
As White kept studying Winckowski, a light went off in his head.
“His back was bent so far to the left side, the arm angle looked like it was over the top,” he said. “He was constantly off balance. As much velocity as he had, he was easy to hit.”
As Winckowski’s described it, “When I threw, it also was like a catapult. I was straight level with the ground with not quite a natural release point. I pulled over to first base and flew open more. It was harder to throw strikes.”
White worked with his student to be straighter and more balanced while throwing from three-quarters angle instead of over the top. He knew this adjustment would take time; but when Winckowski got used to it, he’d be tough to hit.
“I said, ‘You’re young enough to fix this,’” White said. “I also said, ‘You’ll just have to trust me on this.”
White said Winckowski is the most competitive player he’s ever coached. And that was needed because he had to learn while pitching in games. There were some rough outings, but by the end of his junior season, he started to see progress. His velocity increased from 87 to 89 mph.
“He really ironed things out in the summer with travel ball,” White said. “Then he started throwing darts.”
A more mechanically sound Winckowski saw his velocity increase to 92 mph.
Major League scouts started to notice. Early in Winckowski’s senior year he received phone calls. When he pitched during the week, four to 10 scouts came to watch.
Winckowski was set to attend Southwest Florida College, but that changed when the Blue Jays made him the 462nd player chosen.
After moving up Toronto’s minor-league system, Winckowski moved around before the 2021 season commenced. On Jan. 27, he was traded to the New York Mets. Two weeks later, Winckowski was sent to the Red Sox. By now, he could throw his slider between 83-87 mph. He could throw a fastball between 94-96 mph.
In 2022, Winckowski went 5-7 with 5.89 earned run average with the Red Sox while striking out 44 batters in 70 1/3 innings. Rather than getting frustrated by shuttling between Boston and Worcester, Mass., he relished his opportunities.
“It’s not that long of a trip between the two places,” he said. “And anytime you get the call, they trust you’ll be ready.
“In the majors, it’s more about winning and performing. If you don’t perform, the game only gives you so many chances.”
From being around pitchers like former FGCU lefty Chris Sale – who has made just 11 starts the last three seasons because of injuries – he has seen what it’s like to deal with adversity. So he won’t be satisfied.
“As soon as you get complacent, as soon as you think you got baseball figured out, you’ll get a reminder there and there,” Winckowski said.
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