Boston Red Sox chief baseball officer Craig Breslow can cross another name off his list — and not in the way he would hope —as the Red Sox have lost out on yet another race for a notable free agent.

And the loss comes at the hands of Breslow’s old club, the Chicago Cubs, who have put the pen to paper with Japanese pitcher Shota Imanaga on a multi-year contract.

According to multiple baseball insiders, Imanaga’s deal with the Cubs is loaded with various options, esclators, and options that can make it ‘complicated’ to know the full scope of its value. But at the very least, it will be for $30 million over two years, according to a Tuesday evening update from Jon Heyman.

• Shota Imanaga Cubs deal is complicated and includes player/team options and escalators that could boost it to way up to $80M. Guarantee suggested to be somewhere around $30M for two years by @JimBowdenGM @jonmorosi 1st said $15M/year

  — Jon Heyman (@JonHeyman) January 10, 2024

  Chicago’s ability to close the deal on the 30-year-old lefty came with just two days left on Imanaga’s 45-day posting window, with the deadline slated to pass at 5 p.m. on Jan. 11.

• 

  MIAMI, FLORIDA – MARCH 21: Shota Imanaga #21 of Team Japan pitches in the first inning against Team USA during the World Baseball Classic Championship at loanDepot park on March 21, 2023. (Megan Briggs/Getty Images)

  Considered to be among that second tier of free-agent pitching options behind Yoshinobu Yamamoto, Imanaga hit the open market in search of an MLB contract after a 2023 campaign that featured a 7-5 record, 2.66 ERA, and career-high 188 strikeouts for Yokohama.

  And when talking about Imanaga, you were talking about a pitcher with a straight-up deep arsenal, with the ability to work in six different pitches with considerable regularity. Overall, the 5-foot-10 Imanaga was moving to the MLB after a career that included a 74-55 record and 2.96 ERA in eight seasons in Japan.

• And the Red Sox, for what it’s worth, were linked to Imanaga pretty consistently throughout his exploration process. Some even considered them to be among the ‘finalists’ as recently as last week.

  They were even ‘in’ on him when Tuesday began, but their ability to actually land him was considered “doubtful,” according to the Boston Globe’s Alex Speier.

  The Red Sox remained involved in the Imanaga bidding as recently as this morning, but had been described as “doubtful” to land him. https://t.co/KLsTfDP1FN

  — Alex Speier (@alexspeier) January 10, 2024

  This ultimately seems to be the theme when it comes to the Red Sox and their offseason to date.

  It happened with outfielder Teoscar Hernandez, who the Red Sox were linked to all the way up to his signing with the Los Angeles Dodgers while reports suggested that the Red Sox ‘had’ to shed payroll before signing him, and now it’s happened with Imanaga.

• 

  ARLINGTON, TEXAS – OCTOBER 28: Jordan Montgomery #52 of the Texas Rangers pitches in the first inning against the Arizona Diamondbacks during Game Two of the World Series at Globe Life Field. (Jamie Squire/Getty Images)

  As for where the Red Sox go from here, it’s of course worth noting that both Jordan Montgomery and Blake Snell remain in search of homes for the 2024 season. Both players seemingly represent the ‘best options remaining’ on the market’s starting pitching front, but recent reports have indicated that they are — and this is going to shock you, I know — out of Boston’s price range.

  There’s also other second-tier options such as Marcus Stroman, Mike Clevinger, and James Paxton.

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