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3 Players To Watch Series

LOD’s 3 Players to Watch: Boston Red Sox

For this series, LOD writers will pick three players from each MLB team that we feel are players to watch in the 2023 season.

The Red Sox have done a great job over the years of stock piling young talented ball players and even though some don’t make it to the big leagues with the home club, there are a few that are still with the organization that have either gotten their big league debut or on the cusp of making it in 2023.

Check out the three below that are a must watch for 2023.

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Josh Winckowski jumped into the mix of the Red Sox pitching staff rather quickly in 2022 after coming over from the Toronto Blue Jays Organization. The Toledo, OH native who played High School baseball in Estero, Florida was drafted by the Blue Jays in the 2016 June draft; Round 15, 462th overall.

The 6’4″ right hander started 84 of the 90 games he appeared in the minors spanning six seasons, while posting a 29-25 win/loss record, with a 3.57 ERA and 400 strikeouts in 436.1 innings pitched.

On May 28, 2022 he made his MLB debut with the Red Sox as a starter and tossed three innings allowing four runs on six hits, while taking the loss. The young right hander was probably a bit nervous as anyone would be in their 1st MLB start, as he walked two batters while giving up a single in the first inning, but got out of the jam unscathed.  He did show signs that he belonged as he struck out Rougned Odor swinging on a high fast ball for his MLB strikeout. After allowing a two-out single, he struck out Cedric Mullins to end the inning.

In the 4th, the Orioles would finally get to the Rookie pitcher with two singles, a double and a home run as the Orioles put four runs on the board.  But the soon to be mainstay in the rotation, battled back to strike out Ryan McKenna to end the inning and his debut.

Winckowski earned his first MLB win in his next outing by tossing a four-hit shutout through five innings of work and added two more wins by end the month of June. The rookie struggled in July with keeping runs off the board, but mark that up to learning how to pitch on the big league level, especially in his first MLB season. He ended the month with a win, tossing five innings, while allowing two runs on seven hits. In August, he was 1-2, and did not get a decision through his last two starts in September and October. The Estero High School product, finished the season with five victories, while logging in 70.1 innings on the mound as the righty showed that he has the tools to be a successful big league starting pitcher.

On the Red Sox depth chart for 2023, he is slated as one of the starters and will use spring training to see if he can possibly break camp in the rotation that looks to have Chris Sale, Corey Kluber, and James Paxton, all of whom are looking to have comeback seasons. The others vying for starting nods are Nick Pivetta, Garrett Whitlock, and Brayan Bello.

Look out for Winckowski in 2023 as he works his way to earning a spot in the rotation.


Bryan Mata has been with the organization since he signed an International free agent contract in 2016. He has always had success in the minors posting a 29-23 win/loss record, with a 3.21 ERA and 412 strikeouts through 398 innings. The #6 Prospect on the Red Sox Top Prospect list and top pitcher in the organization is poised to show the baseball world that he is ready to take on the big league batters.

After appearing in the World Futures game in 2018, he came out the gates in 2019 for the Salem Red Sox in the High A ball and started 1o games posting a 3-1 record with a 1.75 ERA and 52 K’s in 51.1 innings. The Red Sox then sent the righty to Double A and after winning his first start, he struggled to keep runs off the board and lost three of his next four starts. He battled his way through the season and won his last game impressively by tossing seven innings of shutout baseball, allowing just one hit, and struck out nine batters. He truly left his best for the last game of 2019.

In 2020, he was invited to big league camp, but the Covid-19 Pandemic shut down the minor league season and in April of 2021, Mata was shut down as he had to undergo Tommy John surgery.

In 2022, the Red Sox moved Mata through the minors from Low A, to High A, then AA and lastly AAA and all along the way he was 7-3, with a 2.49 ERA , with 105 strikeouts through 83 innings.

The Maracay, Venezuela native enters 2023 with an opportunity to make the big league club.  It may not happen out of spring training, but as manager Alex Cora was quoted saying that Mata can help the big club win some games. That is a great thing to hear from your skipper.

The 2023 season will be the year that Bryan Mata finally makes his debut.



The #3 Top overall Prospect in the organization and top outfielder Ceddanne Rafaela has improved on every step of the way through his minor league journey. The Willemstad, Curacao native was signed by the Red Sox to a minor league contract in 2018.

In his rookie campaign in the Dominican Summer League in 2018, he batted .271, with nine doubles, two triples, three home runs and 28 RBIs, through 54 games. In 2019, he split time between the Gulf Coast League (Rookie) and Low A ball and even though his batting average dipped to .244, he showed a consistent power bat by hitting six home runs through 44 games in with the Gulf Coast League team.

After the suspended 2020 season due to the Covid-19 Pandemic, Boston sent him to the Low A Salem Red Sox, (the previous High A ball club) and through 105 games, he batted .251, with 20 doubles, nine triples, 10 home runs, 53 RBIs, 25 walks and 23 stolen bases.

The 2022 season was a big one for Rafaela as he showcased more power and consistent hitting from High A ball to Double A. Combined he batted .299, with 32 doubles, 10 triples, 12 home runs and 86 RBIs.

The 5’8″ outfielder will be in big league camp for the first time in his career and is slated to play with Team Netherlands in the World Baseball Classic.

The word on the blogs is that Rafaela is being looked at as possibly making his MLB debut in the second half of the season. So keep an eye out on this young star as he prepares for a big season that will lead to helping out the big club win.

David is the Co-Founder and Executive Editor of Legends On Deck®, as well as a Co-Host on Legends On Deck Podcast. David was a Senior Editor for, and Contributor for that spanned from 2010 to 2014. David made his MLB Debut as a writer in June 2014, while covering the NY Mets at Citi Field, for David also managed his Cape Coral 16U Rec Ball team for the past two seasons and on May 13, 2024 they won their league Championship. On May 15th, David started the first ever Legends on Deck 16U Travel Baseball team in SWFL. David's passion is teaching the game he loves to the future Legends of Tomorrow as well as making available a website that people can have fun sharing and reading. David is also passionate about his career as a Mortgage Loan Officer which allows him to help many families reach their dreams of owning a home. Connect with David via his Social Media pages as he loves to chat all about baseball.

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