The Boston Red Sox entered the offseason in desperate need of starting pitching, leading to the team pursuing multiple top starters then failing to land them. One of those targets, Chicago Cubs pitcher Shota Imanaga, reportedly gave the Red Sox one last chance and they passed on the opportunity.

Imanaga, age 30, has been one of the best pitchers in baseball this season for the Chicago Cubs. After playing for the Yokohama DeNA Baystars of the Nippon Professional Baseball, Imanaga came over to the majors as one of the most coveted starting pitchers in free agency.

• Shota Imanaga stats: 0.98 ERA, 0.8 WHIP, 25.9% strikeout rate, 2.8% walk rate, .181 batting average allowed, 0.65 HR/9 in 27.2 innings pitched

Chicago ultimately won the bidding war for him and he’s been outstanding on the mound. He leads the team in wins (four) and ERA (0.98), carrying a Cubs rotation without ace Justin Steele. The Red Sox saw what he could do first-hand at Fenway Park on Friday – 6.1 innings pitched, 5 hits allowed, 7 strikeouts and 1 earned run – but what might be even more painful is that his start was a reminder of a missed opportunity.

Bob Nightengale of USA Today reported that the Red Sox joined the Cubs as finalists for Imanaga along with the Pittsburgh Pirates and Milwaukee Brewers. While he signed with Chicago, Boston reportedly blew its chance to prevent that from happening.

According to Alex Speier of The Boston Globe, the Red Sox were provided the opportunity to match the CUbs’ offer and they could’ve landed him. Instead, Boston declined in part due to cost but also reportedly because sources believed the team had ‘medical concerns’ with Imanaga.

• Shota Imanaga contract: $9 million salary in 2024, $13 million salary in 2025, $15 million mutual options (2026-’27), $17 million club option for 2028

As noted by Nightengale, Imanaga could opt out of his contract following the 2025 season. However, Chicago also protected itself with the right to give him a three-year extension worth $57 million following 2025. If that is exercised, Imanaga would be paid $20 million annually from 2026-’27 then $17 million in 2028.

The medical concerns are particularly ironic considering Boston’s top free-agent signing, starting pitcher Lucas Giolito underwent elbow surgery in March with an internal brace placed inside his right elbow to repair a damaged UCL. While Imanaga pitches brilliantly for Chicago, Boston is paying Giolito $18 million in 2024 and he was sidelined with season-ending surgery before Opening Day.