For months, the Boston Red Sox were among the most disappointing teams in baseball, hitting 14 games under .500 and in the American League basement at their lowest point. All the while, third-year Chief Baseball Officer Craig Breslow remained confident in his roster, echoing that a run was right around the corner. 

He was right, as the Red Sox have completely changed the tenor of their season thanks to an 18-4 record in July that has propelled the team to the second wild card spot and made them surefire buyers ahead of the Aug. 3 trade deadline. 

Now, Breslow faces his biggest test to date: getting the roster the reinforcements necessary to be the World Series contenders he thought you were entering the season. 

When the Red Sox hired Breslow ahead of the 2024 season, there were expected to be some growing pains as the then-43-year-old took on his first role as the primary decision-maker of an organization. There has been no better example of those growing pains than the trade deadline, where, in his first two seasons at the helm, he has left a lot to be desired. 

With the Red Sox at 56-51 and 2.5 games back of the final wild-card spot in the American League, Breslow took a quantity-over-quality approach to the trade deadline. Making four deals, adding starter James Paxton, catcher Danny Jansen, and relievers Lucas Sims and Luis Garcia for the playoff push. 

The 35-year-old Paxton made only three starts in his second stint in Boston, posting a 4.09 ERA across 11 innings of work before partially tearing his right calf, ending not only his season but also his career. As both Sims and Garcia struggled in the bullpen, combining for a 7.26 ERA in 29.1 innings pitched. 

Jansen was perhaps the biggest miss of the 2024 deadline for Breslow, as the team was in desperate need of a right-handed bat to make up for the loss of shortstop Trevor Story, who underwent season-ending shoulder surgery. In 30 games for the Red Sox, Jansen hit just .188/.323/.300/.623. 

There was, however, one move that may have worked in Breslow's favor as he sent former first-round pick infielder Nick Yorke to the Pittsburgh Pirates for starter Quinn Priester. The then-23-year-old made one start in a Red Sox uniform before being dealt to Milwaukee in an offseason deal in exchange for prospects Yophery Rodriguez, John Holobetz, and a competitive balance selection in the 2025 draft, which was used on pitcher Marcus Phillips.

Overall, Breslow's acquisitions combined for a -0.7 bWAR as Boston finished the regular season 25-30, missing the playoffs for the third consecutive season.

Breslow entered the 2025 deadline with the Red Sox in firm possession of the second wild-card spot in the American League with a record of 59-51, but with two clear areas of need: A power bat to replace the production left behind by Rafael Devers and a "Robin" to Garrett Crochet's "Batman". 

After weeks of rumors linking Boston to Minnesota Twins' ace Joe Ryan, the two sides took negotiations up until the final whistle, but were unable to come to an agreement on a deal. After failing to land Ryan, Breslow was forced to make a last-minute pivot, acquiring Dustin May from the Los Angeles Dodgers for a pair of prospects, outfielders James Tibbs III and Zach Ehrhard. 

May made only five starts for Boston, posting a 5.68 ERA across 25.1 innings before being moved to the bullpen, where he made one appearance before missing the remainder of the season with right elbow neuritis. 

Breslow also acquired left-handed reliever Steven Matz in a deal with the St. Louis Cardinals for first base prospect Blaze Jordan. Matz performed well in his short stint with the Red Sox, posting a 2.08 ERA in 21 appearances for Boston before leaving for Tampa in free agency. 

Unfortunately for Breslow, his failure to add offense was ultimately the Red Sox' undoing as they fell to the New York Yankees in three games in a Wild Card series in which the team scored only six runs.

Across two deadlines at the helm of the Red Sox, Breslow has added six players who combined for -0.5 bWAR as both teams limped to the finish line, finishing 55-52 in the 107 games after the deadline.

Despite poor results in each of his first two trade deadlines, Breslow has given fans some reason to be optimistic, as for the first time in his tenure, he got out ahead of the market, adding power-hitting infielder Curtis Mead in a deal with the Washington Nationals 9 days before the trade deadline. 

However, those good vibes didn't last long as the 25-year-old was hit in his left wrist by a pitch in his second plate appearance in a Boston uniform, breaking a bone and landing him on the injured list indefinitely, leaving Breslow to fill the power void in the lineup once again. 

Unlike in 2025, Breslow has seemingly cast a much wider net in targeting players ahead of the deadline, with Boston linked to nearly every shortstop and catcher who may become available in the days leading up to it, rather than focusing on one particular target, as happened with Ryan. 

Make no mistake about it, though: after back-to-back trade deadline disasters, the pressure is firmly on Breslow to show that he is learning from his prior mistakes and is capable of getting a team that is firmly in the mix the reinforcements they deserve to be one of the best teams in the American League. 

The MLB Trade Deadline is Aug. 3 at 6:00 p.m. ET. 

Boston will look to bounce back from Tuesday night's 4-3 loss to the Athletics in game three of four from Sutter Health Park in West Sacramento. Patrick Sandoval (0-0, 3.21 ERA) will get the start for the Red Sox opposite Jacob Lopez (5-4, 6.12 ERA) for the A's. First pitch set for 9:40 p.m. ET.