The Boston Red Sox were among the most active teams ahead of the trade deadline, landing All-Star catcher Adley Rutschman and infielder Curtis Mead in two of the league's biggest pre-deadline deals. One market the Red Sox were heavily involved in, but did not make a move in, was the pursuit of a long-term answer at shortstop. 

Whether it was Otto Lopez, Zach Neto, Jeremy Pena, or even seemingly untouchable stars like Bobby Witt Jr. and Elly De La Cruz, the Red Sox reportedly checked in on several options to fill the team's shortstop void to no avail. 

As Chief Baseball Officer Craig Breslow looks to add much-needed star power to his lineup, could the team reengage in the shortstop market, hoping the asking price has come down? 

Among the most glaring holes in the Red Sox lineup in 2027, shortstop was at the top. Thanks to injuries and underperformance, the Red Sox used a host of players at the position, including Trevor Story, Marcelo Mayer, Isiah Kiner-Falefa, and Andruw Monasterio. Red Sox shortstops combined to hit .248/.309/.350/.659, ranking in the bottom half of the league across the board, but bottom 10 in slugging percentage (24th), home runs (9, 28th), and weighted runs created plus (83, 23rd). 

As you look across the Red Sox lineup heading into 2027, shortstop is one of a few positions that isn't locked in beyond the season, with Story entering the final year of the six-year, $140-million deal signed ahead of the 2022 season. 

Boston's top organizational prospect and second-ranked prospect in the sport, Franklin Arias, appears to be the future at the position after a breakout season in 2026 that saw him hit .323/.400/.557/.957, with 25 home runs and 28 doubles. He also drove in 91 runs and posted a WRC+ of 145, tying for the 18th-best mark among all minor league hitters with at least 400 plate appearances. 

Arias' breakout campaign, fueled by newfound power, earned him Minor League Hitter of the Year honors in the Red Sox system and Eastern League Player of the Year honors.

Despite his great year and lofty status, the Red Sox seemed willing to trade Arias for a long-term piece at the position. However, after emptying the farm system to land Rutschman, the question is whether or not Boston has the pieces to acquire that "long-term" solution now.

De La Cruz and Witt Jr. seem like pipe dreams, with the former under team control until 2030 and the latter under a seven-year, $148.78 million deal that will keep him in Kansas City until at least 2030. However, it's equally unlikely the Red Sox have the assets to land either superstar, even if they were ever made available. 

Beyond De La Cruz and Witt, the position lacks much star power. Lopez is a fine player under team control through the 2030 season; however, the Red Sox may be better off sticking with Arias than meeting the asking price on a player who isn't a true bona fide star. The same goes for Neto, a fine player who posted a respectable slash line of .239/.330/.436/.766, with 27 home runs and 31 doubles, but a 30.5 strikeout rate that was the ninth-highest among all qualified hitters. 

Finally, there's Pena, who is arguably the best of the non-Witt, De La Cruz players. The 2022 World Series MVP with the Houston Astros hit .277/.325/.477/.802 with 22 home runs and 19 doubles in 112 games in 2026 while providing outstanding defense at the position. After choosing to hang onto the 28-year-old through the deadline, the Astros figure to try to find a trade partner ahead of his final year of team control. That's where the problem lies for the Red Sox. 

After expending a ton of prospect capital to land Rutschman, who is also set to hit the open market after the 2027 season, will Breslow want to potentially move Arias for one year of Pena and then have to issue two hefty contract extensions after the season or risk losing one or both of Pena and Rutschman to free agency? 

Whichever way you look at it, there is no perfect solution to turn the Red Sox into a World Series contender, unless Breslow is committed to paying whatever the ask may be to land a player of De La Cruz or Witt's caliber if they do become available. It all circles back to what is becoming an early theme of the Red Sox offseason: creativity. Whichever path Breslow takes to build the 2027 Red Sox, it will require serious creativity as he navigates an uncertain labor situation, a tighter-than-expected budget, and a free-agent class and trade market that seemingly lacks top-end, controllable talent. 

Of note

Looking for more on the Red Sox needs heading into the offseason? Zach Coe and David Azer are back on the 'Entering Kenmore' Podcast discussing how close Boston is to winning a World Series, whether the 2026 season was a success, and whether fans should have faith in Craig Breslow's ability to build a World Series contender. Check it out wherever you get your podcasts, or in the YouTube player below: