Pittsburgh Pirates 2022-23 Winter League Recap

The Pittsburgh Pirates had a lot of players in winter ball this year, with the large majority playing in Australia, Colombia and Puerto Rico. They also lost numerous players during the winter season, either through waivers or the minor league Rule 5 draft. It was a busy winter if you include everyone. We will just focus here on the players still in the system. Here’s a breakdown by each country.


Starting in Australia, where the most action went on, the Pirates sent six players to the Sydney Blue Sox.

Jase Bowen hit .268/.329/.417 this winter, while mostly playing outfield, but he continued his trend of moving around for versatility, which should help him progress through the minors. It was a nice showing for Bowen, who struggled in his somewhat brief time with Greensboro in the second half of 2022.

Sammy Siani was the best Pirates hitter of the winter, at least once you factor in level of play compared to the player’s experience. His most impressive accomplishment may have been the improvements on his contact skills. He finished with an .899 OPS in 39 games, while dropping his strikeout rate from 36.2% during the regular season, down to 22.4% in the winter.

Dylan Shockley had a chance to make up for lost time during the season. His defense really impressed this winter, while his offense struggled a bit with a low average, but he showed some power later in the year. He thrived with regular playing time once he knocked off the rust from the missed time.

Solomon Maguire has missed a lot of time in pro ball due to three different injuries in two years. His time in Australia allowed him to learn a lot from playing against older competitors. He did very well for his age/experience in his home country, putting up a .238/.282/.313 slash line in 26 games, with a 20% strikeout rate.

Jesus Castillo was in over his head on offense, though his age/experience wasn’t ideal for the Australian League. However, his defense excelled in the league, with one error in 138 chances at shortstop. That’s extremely impressive at any level. He posted a .398 OPS, with his lone highlight being his strikeout rate, which was better than league average.

Ernny Ordonez was getting on base more often early on, then showed power over on base later, finishing with league average stats (.726 OPS) in his 39 games. He mostly played first base, but he saw time at four spots.

Puerto Rico

Tsung-Che Cheng played winter ball in Colombia last year and had a strong off-season. That was followed by an All-Star season in the Florida State League with Bradenton. He got bumped up quite a bit with his assignment to Puerto Rico this winter, and had some trouble with the jump in competition. That’s not completely unexpected due to his experience and the advanced placement.

Despite a .513 OPS in 19 regular season games (plus he played three playoff games), the Pirates were impressed with the work Cheng has put in this winter. He will be representing Chinese Taipei in the World Baseball Classic next month.

Duane Underwood Jr. was one of the best players in Puerto Rico this winter. As you might have suspected, he dominated the league in his brief time, which also included some playoff action. He’s going to be playing for Puerto Rico in the World Baseball Classic.

Brad Case had a lot of success this winter while working on a new slider. The bullpen the Pirates sent to Gigantes de Carolina dominated as a group. Case allowed two runs over 11 innings, and one of those runs was a rough one to take. He retired five batters in a row, allowed a two out single, then got pulled for a reliever who gave up two hits to score the run.

Will Kobos was also in that Carolina bullpen, where he allowed one run in 10.2 innings, while striking out 15 batters. He pitched just 21 innings during the regular season due to multiple trips to the IL, so he needed a big winter.

Jeffrey Passantino was the third piece in that Carolina bullpen. He allowed one run over 11.2 innings, while posting an 0.86 OPS. The only odd thing about his season was that he did that while striking out just three batters.

Aaron Shackelford played one game before a wrist injury ended his winter. Will Matthiessen eventually took his place, but he saw very little time. He went 0-for-10 with two walks in four games.

The Pirates picked up outfielders Josh Palacios (Rule 5) and Chavez Young (trade) mid-season this winter. Both saw regular playing time at the end of the winter, and then continued into the playoffs. Both will also be competing in the World Baseball Classic. Neither put up big numbers in the regular season this winter, though Young had a nice run in the playoffs.

Shawn Ross was a minor league signing this off-season as a non-drafted free agent. Puerto Rico was an advanced placement for him, though he’s from Puerto Rico, so it made the most sense. He really struggled, putting up a .119 average and a 40% strikeout rate in 100 plate appearances.


Colombia was busy from the start, though they lost Cristian Charle in the Rule 5. Both Eddy Yean and Johan Montero were supposed to pitch, but never played this winter. Santiago Florez is from Colombia, but he didn’t play either, though he’s going to play in the World Baseball Classic. That still left six Pirates who saw action.

Andres Alvarez was making a run at a league triple crown until the final week of the season when a player drove in eight runs in one game and pulled away in the RBI race. This league was not a good level for him, but our Winter Report (with help from Alvarez and his manager/Pirates FCL manager Jose Mosquera) showed that he was getting a lot of value on defense/versatility from the league.

Francisco Acuna’s winter couldn’t have gone any better. He played a full season. His team didn’t finish first, which meant he got a semi-final playoff series, then a finals, where his team won the league title. That was followed by nine more games in the Caribbean Series, where he reached base safely in every game. Basically, he played a lot of winter ball. That’s good because he was suspended for PEDs late in 2022, and he will miss the start of the 2023 season.

His winter started slow, but he finished the regular season strong. His playoffs were not great, though he had a couple of big hits for his team. He did outstanding in the Caribbean Series.

Rodolfo Nolasco had about two solid weeks in Colombia, which was the perfect level for him this winter with his experience. He’s Dominican, and has a team that owns his rights in that league, but that league is far too advanced for him at this point. He started off the winter slow and ended slow, leading to poor overall numbers (.195 average/.645 OPS) and a high strikeout rate. This was a disappointing showing for the young power hitter.

Diego Chiquillo only has DSL experience in pro ball, so the league in Colombia was too advanced for him. However, he’s from Colombia, so that’s where he’s going to play if he’s involved in winter ball. Walks were a major issue for the young pitcher going up against more experienced hitters. The overall results were poor.

Oliver Mateo didn’t see a lot of action, but he piled up the strikeouts, and was impossible to hit. He was hurt by control a little, which has been a career-long issue. He missed time during the regular season with Greensboro, so the extra innings this winter helped him out.

Adrian Florencio got into a few games, getting roughed up as a starter early, before putting together a few good appearances to finish well. He had a very rough season in Greensboro, after being named as our 2021 Pitcher of the Year. He’s in the same situation as Nolasco, where his rights are owned by a team in the Dominican, but the league is far too advanced for him at this point.

Dominican Republic

The Dominican had some name power, but it ended up rather quiet for what is usually a good league for content. We followed Lewin Diaz for as long as he was with the Pirates.

Endy Rodriguez, Liover Peguero, and Dariel Lopez all saw action early in the year, but once the more experienced players started playing, they were all done by the end of the first month.

The experience is great for the younger players, but it was all small sample sizes when the league wasn’t at its peak. By mid-season, some of the teams in the league were loaded to the point that they were throwing out lineups that were as good as the worst MLB teams.

Peguero was one of our early Winter Report articles. Lopez did very well on offense in his brief time, but he had defensive issues. Rodriguez had a .490 OPS in six games.

Rodolfo Castro had a rough start to his winter. He finished with a .225 average and a .623 OPS in 29 games. He also committed eight errors in his brief time, so it was not a good off-season from someone with his type of big league experience.

Osvaldo Bido had a terrific winter as a starter at the beginning of the year. Even with one poor start in a small sample size, he had a 2.53 ERA in 21.1 innings over six starts. He showed an ability to miss bats in Indianapolis this past year, but inconsistent starts led to bland overall results. A combination of his winter results and ability to miss bats would get him to the majors this year.

Miguel Andujar got off to a strong start this winter, then finished with a .247/.304/.353 slash line in 21 games. The Pirates designated him for assignment during the end of the winter season, but he cleared waivers and remained in the system.

Oneil Cruz and winter ball were not meant to be. He came out and said he would play all winter this year, missing just the start of the season. Then his debut kept getting pushed back. Once Cruz started playing, he was sick for a few days, had dental work that kept him out, then had a minor ankle injury that he claimed was nothing multiple times, but it still ended his season after just 12 games. He had one big game in a mostly quiet winter.

Yohan Ramirez was a silver lining in the Dominican, with one run over ten innings in 11 appearances. That should help him as he moves towards winning a bullpen spot this spring.

Lolo Sanchez saw very limited time off of the bench. He would have seen more playing time if he was around at the start of the winter instead of the middle/end when the talent was at its peak.


The winter was fairly quiet in Mexico. We followed Jared Oliva for a few months, until he was taken in the Rule 5 draft. That left us with outfielder Fabricio Macias and pitcher Denny Roman.

Macias was steady all winter, finishing with a .252/.298/.358 slash line in 60 games. That’s not bad considering his age/experience in that league.

Roman has less pro experience, but he has pitched in Mexico before. He had a 1.02 ERA in 17.2 innings over 14 appearances. His worst outing came during his second (of two) playoff appearances.


Venezuela wasn’t quiet in the winter until it was quiet. Diego Castillo, Ali Sanchez and Miguel Yajure were all playing at the time that they were lost on waivers.

The only other player to see action was Angel Basabe, who was around just long enough to play a doubleheader on the final day of the season. With only brief Single-A experience to his credit, he is still probably 2-3 years away from playing winter ball full-time.

Castillo was one of our early Winter Report subjects.

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.

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I just hope Siani can continue that 22% K rate at Altoona. Maybe one day we don’t have to say ‘We shudda taken Gunnar’??


Very impressive season for Siani

Combined with his time in Greensboro his season stats start to look OK

15 HR
29 SB (4 CS)

Triple slash of roughly 0.230 / 0.330 / 0.370

And good OF D


He learns how to put the ball in play more often and all those numbers will grow. 36% SO rate will get him nothing but a new career.

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