Tsung-Che Cheng’s path from former Pittsburgh Pirates top prospect to unlikely contributor for the Boston Red Sox has been anything but straightforward.
Over the span of roughly six weeks this winter, Cheng belonged to five different MLB organizations. Such is life on the margins of a 40-man roster, where one transaction can suddenly make somebody expendable.
What makes Cheng’s story unusual is what happened next. Rather than disappearing into Triple-A depth somewhere, Cheng emerged as a useful piece of a Red Sox team that rattled off a historic 15-game winning streak before finally falling 5-1 to the Baltimore Orioles on Wednesday.
Cheng has hardly become Boston’s offensive centerpiece. Batting ninth, his job is mostly to make the occasional contribution at the plate and let the bigger bats behind him do the damage. Defensively, though, he has reminded everyone why he was once viewed as an intriguing prospect in Pittsburgh’s system.
Tsung-Che Cheng: ATHLETE pic.twitter.com/ZAeNjdbv8a
— NESN (@NESN) July 18, 2026
Tsung-Che Cheng's flashy defensive plays helped surging Red Sox complete historic 15-game win streak
Cheng signed with the Pirates as an international free agent out of Taiwan in 2019 and eventually worked his way into the organization’s upper levels. His glove at shortstop was always one of his calling cards, even as questions remained about whether his bat would allow him to stick in the majors.
The Pirates ultimately decided they needed Cheng's 40-man roster spot to complete the Brandon Lowe trade in December, and that started a transaction whirlwind. Pittsburgh designated Cheng for assignment, and the Tampa Bay Rays claimed him on Jan. 7 — only to waive him less than two weeks later. The New York Mets claimed him Jan. 16. The Washington Nationals grabbed him Jan. 28. Then, on Feb. 6, Boston became his fifth organization in barely a month.
The Red Sox easily could have continued the cycle. Instead, they held onto him in a decision that looks pretty smart now.
ANOTHER SENSATIONAL PLAY FROM CHENG TO SECURE THE W!
— NESN (@NESN) July 22, 2026
15. IN. A. ROW! 🤯 pic.twitter.com/LnY3cu8vBk
Cheng’s emergence doesn't necessarily mean the Pirates made some catastrophic mistake by letting him go. Players like him get caught in roster crunches all the time, and Pittsburgh had legitimate reasons to prioritize other pieces.
Cheng didn’t suddenly become a superstar after leaving Pittsburgh, but he became a dependable major leaguer who could play premium defense, occupy the bottom of the lineup and help a contender keep winning. For Boston, the results speak for themselves.
After spending the winter getting passed from organization to organization, Cheng finally found one willing to keep him. Then he helped make history.
