Pirates Hire Veteran Pitcher Alessandro Maestri as DSL Pitching Coach

The Pittsburgh Pirates have hired Alessandro Maestri, who pitched 15 seasons of pro ball, as one of their two Dominican Summer League pitching coaches.

Maestri was born in Italy and he was signed by the Chicago Cubs in 2006. He made it up to Double-A in their system. From 2011-20 he played in independent ball, Japan, Korea, Mexico, Italy, and Australia. He went out on a high note in Italy in 2020, going 7-0, with a 1.01 ERA in 44.2 innings, along with an 0.92 WHIP and 63 strikeouts.

After retiring following the 2020 season, he began coaching in Italy. He has helped the Pirates with pitcher Alessandro Ercolani, the 18-year-old pitcher from San Marino, which in turn led to an opportunity with the Pirates last year.

Maestri was supposed to accompany Ercolani to the U.S. at the start of minor league Spring Training last year, but last minute travel restrictions led to just Ercolani making the trip. When the Pirates had extra pitchers in Extended Spring Training late in April, they asked Maestri if he could help them for a short time as an added pitching coach. He ended up spending three weeks with the team at Pirate City.

The Pirates must have liked what they saw from his work with the pitchers during that brief time, because now he will be helping out with their younger pitchers down in the Dominican Summer League.

Tony Harris is a scout for the Pirates in Australia, and the manager of the Sydney Blue Sox. He was Maestri’s manager for two years recently, and saw him put up a 2.98 ERA over 17 starts. I reached out to Harris to get his reaction to Maestri’s hire.

“I recruited Alessandro into Sydney a few years back and he pitched us into a preliminary final as our #1 starter,” Harris said. “He always had the traits of a leader. Uber professional, and a student of his game. He’s a quality person both on and off the field. He’s a great fit for the younger pitchers in our organization.”

John started working at Pirates Prospects in 2009, but his connection to the Pittsburgh Pirates started exactly 100 years earlier when Dots Miller debuted for the 1909 World Series champions. John was born in Kearny, NJ, two blocks from the house where Dots Miller grew up. From that hometown hero connection came a love of Pirates history, as well as the sport of baseball.

When he didn't make it as a lefty pitcher with an 80+ MPH fastball and a slider that needed work, John turned to covering the game, eventually focusing in on the prospects side, where his interest was pushed by the big league team being below .500 for so long. John has covered the minors in some form since the 2002 season, and leads the draft and international coverage on Pirates Prospects. He writes daily on Pittsburgh Baseball History, when he's not covering the entire system daily throughout the entire year on Pirates Prospects.

Support Pirates Prospects

Related articles

join the discussion

Notify of
Oldest Most Voted
Inline Feedbacks
View all comments

I hope he can speak Spanish?

b mcferren

nice name for a teacher

Wilbur Miller

If this guy had a hand in Ercolani’s performance so far, then 👏


DEVELOPMENT. (Lit up in flashing, neon lights…)

Identifying the right coaches is imperative; I like the direction chosen By Baker.

Share article

Pirates Prospects Daily

Latest articles

Pirates Prospects Weekly

MONDAY: First Pitch

TUESDAY: Article Drop


THURSDAY: Roundtable

FRIDAY: Discussion

SATURDAY: Pirates Draft Report

SUNDAY: Pirates Business

Latest comments

Would love your thoughts, please comment.x