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.”