The Cubs and the player are reportedly working out a 2024 contract. Whether this is a big league or minor league agreement is still up in the air.

The Pirates selected 31-year-old Brewer in the fourth round of the 2011 draft. Brewer made his big league debut with the Padres in 2018 after spending several years in the Pirates and Yankees farm systems; however, the right-hander struggled to a 5.59 ERA across 11 appearances in that maiden season. The right-hander then joined the Red Sox, with whom he played for the majority of his major league career. Brewer pitched 81 1/3 innings over three seasons with Boston, posting a 4.98 ERA and 5.20 FIP. Brewer walked an astounding 13.3% of hitters encountered during his tenure with the Red Sox, despite striking out a reasonable 20.3% of batters faced during that time and producing a strong 50.4% groundball rate.

The club designated Brewer for assignment back in June 2021 as a result of those control concerns. After being outrighted to Triple-A, he played in the minor leagues for the rest of the season. In the offseason that followed, he signed a minor league contract with the Royals, although he was limited to the minor leagues for the entire 2022 campaign. Brewer pitched 57 2/3 innings at the Triple-A level over an 18-month stay, recording a comparatively meagre 4.53 ERA but maintaining a walk rate of more than 10%.

Despite not making it to Opening Day as a member of the team, Brewer nevertheless signed a minor league contract with the Rays in the 2022–2023 offseason. Instead, just before the season began, the Rays and Yankees worked out a little deal that sent Brewer to the Bronx to join the team’s 40-man roster. Despite having a 4.32 ERA in 8 1/3 innings of work with the major league team, he was designated for assignment in the middle of April.