Matt Chapman or Robbie Ray? Which current Giant should Blue Jays have kept longer?

At one point in their careers, third baseman Matt Chapman and pitcher Robbie Ray could have signed long-term deals to extend their tenures with the Toronto Blue Jays. Neither of them did and today (Sunday) both of them will suit up as members of the San Francisco Giants to take on the Blue Jays at Rogers Centre.

During their time with the Blue Jays, both Chapman and Ray were a part of seperate playoff runs for the Blue Jays. Ray helped the 2020 squad make it into Covid-season expanded postseason, but left Toronto after the 2021 campaign. Chapman joined the Blue Jays via trade in the 2021 offseason, and after making it to the playoffs in 2022 and 2023, he left as a free agent.

With both players doing their part to help the Giants chase a spot for the 2025 MLB Postseason, we can reflect on both of their careers and make a case for whether the Blue Jays should've kept Chapman or Ray.

Why Blue Jays should've kept Ray or Chapman

In both years Chapman was a member of the Blue Jays, Toronto made the postseason but were swept in the Wild Card series. Chapman, a three-time Gold Glove winner before joining Toronto, brought his elite defense to the Blue Jays as well, earning a Gold Glove award in 2023. He was the first player to earn that award at the Hot Corner for the Blue Jays since Kelly Gruber in 1990.

However, Chapman struggled offensively. While he had a good power hitting year in 2022 (27 home runs, 116 OPS+) he also struck out 170 times. In 2023, his power numbers dropped hitting 10 less home runs and recording 22 less runs batted in from the previous year. After 2023, Chapman joined the Giants and won a Gold Glove in 2024. He posted another strong power year as well in his first season in San Fran (27 home runs, 124 OPS+), but his numbers in 2025 are down.

For Ray, his success in Toronto was evident. Ray was acquired by the Blue Jays in a trade with the Arizona Diamondbacks mid-way through the 60-game season in 2020. Ray went 1-1 with a 4.79 earned run average in five games (4 starts) while the Blue Jays made the 2020 postseason, but his 2021 season is where he dominated.

In 2021, Ray won the American League Cy Young award, something not many experts saw coming considering he didn't make the All-Star Game. Ray recorded a 13-7 record with a 2.84 ERA. Ray also led American League pitchers with a 6.9 WAR and 193.1 inning pitched, while leading all of MLB with 248 strikeouts. Solid numbers from the southpaw that got helped get the Blue Jays to within a game of a playoff spot.

However, Ray was a free agent after 2021 and the Blue Jays didn't end up re-signing him. He chose to sign with the Seattle Mariners while the Blue Jays brought in former Giant, Kevin Gausman and former Seattle Mariners pitcher Yusei Kikuchi.

While Gausman had a great season in 2022 for Toronto, Kikuchi was a little more inconsistent with the Blue Jays and didn't replace Ray's Cy Young numbers. Ray was also a needed left-handed pitcher that the Blue Jays were lacking in their rotation.

What stung more for the Blue Jays in 2022 is Ray was a member of the Mainers team that defeated the Blue Jays in the Wild Card series. A gut punch to Blue Jay fans' stomachs considering Ray was a solid Blue Jay that was on the opposite side celebrating a playoff series win in Toronto.

While Ray never returned to his Cy Young form with the Mariners, and was battling injuries over the last two seasons, he has redeemed himself in 2025. Ray made the All-Star Game in 2025 and is solid for the Giants, with a 9-3 record and a 2.65 ERA.

The Blue Jays and Giants have both had turnaround seasons in 2025, but keeping Ray over Chapman would've been a big move for the Blue Jays after the 2021 season as it would have provided their rotation with a lot more depth and stability as they navigated through a handful of pitchers, over these last few seasons. From openers, to bullpen days, to spot starters, having Ray with the Blue Jays could have made a big difference.