New Red Sox chief baseball officer has a tall task ahead of him, trying to bring a fifth-place club back into contention in a stacked AL East. Perhaps the hardest part of his job will be improving a starting rotation that finished with a bottom-ten ERA and FanGraphs WAR last season. Indeed, while the Red Sox have starting pitching depth, their rotation has too many question marks and not enough top-end talent. is a lock for the 2024 rotation. So is 24-year-old , who pitched to a 4.24 ERA in 28 starts last year. After that, the Red Sox have four more experienced arms who will stretch out to start this winter but could move into a bullpen role at any time: , , , and . All four have made at least ten starts and at least ten relief appearances over the past two years. With a rotation led by an aging, oft-injured veteran followed by a still-developing young starter and four guys who have bounced in and out of bullpen roles the past years, its clear the Red Sox could use a lot more stability and at least one front-line pitcher. Its not surprising to hear Breslow call rotation upgrades his top priority as the Red Sox navigate the offseason (links via and of Ma sLive.com). Breslow expre sed optimism about Sales health, at least publicly voicing confidence that the lefty could hold up over a full, healthy season in 2024. Of course, thats quite a charitable outlook for a pitcher whos totaled just 151 innings over the past four seasons. Granted, 102 2/3 of those frames came in 2023, when Sale worked to a respectable 4.30 ERA with excellent strikeout and walk rates of 29.4% and 6.8%, respectively. But Sale still mi sed two months last summer with a shoulder injury, and in the three seasons prior he underwent Tommy John surgery, suffered a stre s fracture in his ribcage, broke his wrist in bicycling accident and sustained a broken a pinkie finger on his pitching hand upon being struck by a comeback liner. The Sox dont have much choice but to hope Sale is healthy this year hes entering the final season of his five-year, $145MM contract but recent history is not on their side, regardle s of whatever optimism the teams bra s wants to forecast. Even if the Sox Gary Payton II Jersey were able to somehow manifest a 32-start season from Sale, thered be need to further solidify the group. For his part, Breslow pledged to be as aggre sive as we po sibly can to fill the rotation ( ), be it via free agency or trade. Boston has already been linked to , and in free agency. McCaffrey indicates that the Sox had an initial Zoom meeting with Yamamotos camp (as has been standard for interested teams thus far) but adds that a team official declined to state whether the Red Sox were in position for a forthcoming in-person sitdown with the NPB ace. Breslows pledge to be as aggre sive as po sible is sensible for a team with a projected payroll ( ) thats more than $10MM shy of their end-of-season levels and a whopping $64MM short of their franchise-record Opening Day mark of $236MM. That said, its also somewhat at odds with prior reporting on Bostons rotation search. McAdam reported last month that the Sox before free agency, notably specifying that at that point, they had not yet been active in the market for . The previously mentioned piece from McCaffrey quotes Breslow in acknowledging that the Sox will have to be willing to give up position player capital in order to bolster the starting staff, though McCaffrey notes that the Sox arent likely to trade top-end prospects for pitchers with only one year of club control remaining. Thatll make names like , and division foe particularly difficult to obtain. And just yesterday, Alex Speier of the Boston Globe reported that Boston prefers to . Theres room to be aggre sive within a fairly measured set of free-agent and trade targets, but whether avoiding qualified free agents and one-year rentals is truly acting as aggre sive as we po sibly can is up for debate, at the very least. Its understandable that Breslow, particularly in his first season on the job, might not want to reckle sly spend and saddle the club with a long-term contract or deplete the farm system hes still learning, but imposing those limitations on his front office only makes the goal of bettering the starting staff in a meaningful way all the more daunting. Of course, the goal in the long term is to better the organizations ability to develop its own pitchers. To that end, the Red Sox announced yesterday that theyve hired Twins minor league pitching coordinator Justin Willard as their new director of pitching. Were really excited to bring him on board, Breslow said ( ). Someone that comes with a pretty strong track record of pitching development. Weve been mindful of what Minnesotas done over the last few years in the development of some of their guys. We feel really lucky, really fortunate. The Twins have had some succe s stories with late-round starters, as both and have reached the Majors and held their own (a good bit more than that in the case of Ober, a 12th-rounder). The Twins bullpen has seen multiple names emerge from within the system as well, headlined by closer and setup man . Willard will join newly hired pitching coach in working with Breslow and the rest of the Boston baseball ops and player development staff to hopefully optimize the Sox pitching development systems. While each of Bello, Houck and Crawford has had some big league succe s, theyre all still relatively inexperienced. The Red Sox have regularly relied on free agency and the trade market to round out the pitching staff over the past decade, but theyve struggled to supplement those high-profile additions (e.g. Sale, Rick Porcello, , ) with cost-effective arms produced by their own system. Troy Brown Jr. Jersey