Baseball can be a tumultuous journey, and Maestri has learned firsthand. America's favourite pastime will bring you in, get you hooked, and help you discover a love and a passion that you never knew before.
But it can also break your heart.
The game has taken Maestri all over the world, his baseball resume not short on accomplishments. He was the first Italian-born pitcher signed by one of Major League Baseball's 30 teams, the Chicago Cubs, and he was an all-star in two of his first three professional seasons.
He also played for Team Italy in the first two World Baseball Classics, with a third one on the horizon coming up in March.
After having his heart broken when he was released by the Cubs, he played a season of independent ball. The game then brought the Italian ace right-hander down under, where he impressed immediately and gained back the confidence he had lost.
A RENAISSANCE IN BRISBANE
The Italian Stallion led the Brisbane Bandits pitching staff both on the field and in most statistical categories. He was an Australian Baseball League all-star, and was also named the fan favourite of the entire league.
What Maestri accomplished down under did not go unnoticed. After the season ended and the 27-year-old went back home to Cesena, he soon heard from an independent team in Japan. The Kagawa Olive Guyners expressed interest in the righty and he ventured over to play in yet another part of the world.
Despite only playing for the Guyners for just over two months, he was twice named the league's pitcher of the month.
Now he is once again working his way up to the big leagues, but this time in Japan, after signing a contract to play with the Orix Buffaloes. He is currently on their farm team, with the hope that he will soon be heading to the majors.
Who was the right-handed hurler most excited to share his news with when he learned of his potential call-up to the Buffaloes?
"I definitely called my parents right away," Maestri said. "I told my parents that it was probably going to happen even before it did. They knew I had a chance to sign and they were really happy for me. They know I went through a tough time when I was released by the Cubs and I played independent ball. They're happy that I'm in affiliated pro ball."
Brisbane's front-of-the-line starter has always been impressed by the support that his family has given him. They've been there through the countless number of days, months and years that he continued to try and live his dream.
Maestri's brother, Francesco, has probably been his most vocal supporter, following absolutely everything that his younger brother does through both the media and in talking to Alex. Francesco shares all of the stories that are posted about his baseball-playing brother on a website that he created for him (after translating it all into Italian of course).
The younger Maestri was incredibly excited to learn in recent days that his brother would be coming to visit him in Japan, getting to see him play professionally in person for the first time in a long time.
"I've finally got somebody who actually loves me," Maestri said jokingly. "But no really, I'm happy that he's coming. I'm excited. This is the first time that somebody has actually come to visit me."
It's been hard for the pitcher's family to be able to see him play in person since he rarely plays at home in Italy, and an intense fear of flying has been a preventative factor for an immediate family member.
In the few months that Maestri has been in Japan, however, he has developed a good network of people to hang out with and to help him out around the foreign country. In Kagawa, he spent a lot of his time with a teammate from Dominican Republic, and, since he's been living in Kobe, he is now much closer in proximity to fellow Bandits pitcher Steven Chambers, who is playing for the Yamato Samurai Reds.
"My brother's coming to visit of course," he said. "And then I've been lucky because I've got Steve and now he's not too far away so I can hang out with somebody that I know every once in a while. Then there's a Japanese guy that used to play in Italy and he lives in this city. He always takes me out, even just for dinner. He keeps me busy. It's pretty cool."
NEXT STOP: ORIX
Maestri has so far enjoyed his time with the Orix Buffaloes organisation, but he's only been with them for a short time since officially signing on July 9.
"It's been a gradual process," he said. "My team [in Kagawa] started telling me that Orix had an interest in me and I knew about it a couple of weeks before I actually signed. I couldn't tell anybody but I kind of knew that it was going to happen. I was hoping more than anything but it started getting more sure as the days went on."
The Buffaloes first saw Maestri pitch near the start of his stint in Japan and likely followed his progress with the Guyners from then until the deal was done.
"We actually played against this team with our team probably two months ago," the righty said. "We played against them and the guy that I talked to from the team; he told me that they were really looking at me. Then I guess that was the last test, when I pitched against them. I went two innings and my second inning was pretty good so I guess that's when they decided to sign me."
Maestri's impressive run in Kagawa saw him take on the role of the team's closer. He was incredibly dominant, earning the top pitching award for both May and June, though he doesn't believe he should have been given the honour for a second consecutive month.
"It was two in a row," he said of the awards. "But in the last month that I won, we didn't play that many games. It rained a lot and honestly, I didn't feel like I deserved it. I only pitched like 13 innings. I pitched in most of the games we had but we didn't have that many games. I did well but, I don't know."
Well, the rest of his team knew. The fans did too, as the Guyners hosted a ceremony for Maestri before he left to join the Buffaloes, to show their appreciation and gratitude for what he had done for the team. Their closer also got a chance to thank them.
"After the last game that I played there they just told all the fans that I was going to leave," Maestri said. "My teammates had a present for me on the field and then I had to talk to say goodbye to the fans.
"I actually read a speech in Japanese that my teammates helped me to write in their language. So I had the microphone and I spoke in Japanese to all the fans. It was good."
It is no surprise that Maestri is a fan favourite no matter where he is playing, and it likely won't take long for him to make his mark with his new team. For now, he's only appeared in one game with the Buffaloes, and he is still not sure what his long-term role with the team will be.
"I've only pitched one time with the new team and it was just as a reliever," he said. "I pitched the seventh inning the other day. [On Monday] I was warming up in the sixth and seventh but I didn't get into the game. I might end up being a starter here. I don't know yet. I don't think they know yet either. I think they're still trying to figure it out."
Unfortunately for Bandits fans, the Japanese baseball season stretches into November with a fall league and an instructional league after the regular season is finished.
"Being here, I don't know if I'm going to be able to go back to Australia this year, but I'm going to miss it if I can't. I would have liked to go back there and play again in Brisbane.
"But right now it looks like I'll be done at the end of November and then they start playing again in February. On the first day of February, you've got to be here. It's only two months off. And they tend to throw a lot here so I think in November I might be tired.
"I'll miss Australia. But the season is months away from now so we'll see what happens."