How the Red Sox can turn a wild card exit into a World Series championship

Boston is a town blessed with tremendous sporting success. We claim 38 championships in hockey, basketball, football, and baseball combined — we are literally one of the winningest cities in America. 

2025 was another opportunity for Boston to add to its championship record. Unfortunately, the World Series-contending Red Sox could not go the extra mile. Stymied by the Yankees, this year’s first-round playoff exit for the Red Sox marked the end of a season that started with uncertainty and ended with the same. Yet, if the front office plays its cards carefully, there can be much to look forward to in 2026. 

First, growth follows the numbers. In 2024, the Red Sox had a cumulative revenue of $514 million, according to a CNBC report. This year, the Sox had an estimated payroll of just over $200 million. Thus, the team has a good amount to spend on building a winning squad. 

One of the main focuses for the front office needs to be re-signing third baseman Alex Bregman. As of the writing of this article, Bregman has become a free agent following his decision to opt out of his 2026-2027 contract options with the Sox. At this point, Bregman is on the open market for other teams to pursue. So the question is: do the Sox replace Bregman with young shortstop Marcelo Mayer at third base? Do they offer more money to Bregman? Or should they let him walk and replace him with a slugger of the same caliber?

My first instinct is to say, “Let Bregman go and have Marcelo play third base.” However, there are implications to losing Bregman. The Sox would give up a well-rounded player with above-average defense and hitting skills. He has also been cited as a leader by fellow players and manager Alex Cora. They’d also likely lose Bregman to a big-market rival. There’s not enough risk-to-reward in letting a rookie like Mayer take the majority of games at third base, especially as he’s a traditionally trained shortstop. In my eyes, $80 million or more is money well spent on Bregman, especially if he can stay healthy for the next two to five seasons. 

The second thing the Sox need for 2026 is solid starting pitching. Garrett Crochet had a Cy Young-caliber season, but outside of Crochet, the team’s pitching proved shaky and unreliable. This is where the Sox need to start signing players. Talented starters like righty Dylan Cease — who has a career ERA of 3.88 — would be the perfect signing for the Sox. He’s a proven power pitcher, meaning that he would fit in perfectly with a rotation that features another fireballer in Crochet. The Sox should lock him up for five to six years, at $120 million in total contract value — about $20 million a year. 

Next on the signing block is first baseman slugger Pete Alonso, who is a free agent. Earlier in 2025, first baseman Triston Casas suffered a severe knee injury, rendering him unable to play for the rest of the season and into next year, leaving him only as a trade piece for Boston. The first baseman slot is extremely important; it’s a position with a high percentage of players who swing for power, netting high extra-base hit totals. Alonso is entering his age-31 season and has been hitting with excellence. With the Mets in 2025, Alonso put up a .272 batting average while roping a league-leading 42 doubles. Alonso at first base would provide the Sox a boost in pure power — he also hit 38 home runs in 2025, thirteen more than any hitter on the Red Sox. 

Finally, the Sox need to make big offseason trades. I wouldn’t be opposed to a package deal that involved some of the Sox’s outfielders. Outfielder Jarren Duran, who is at his highest value to date, and platoon player Masataka Yoshida should be at the top of trade considerations, alongside prospects such as Jhostynxon García, who finished 2025 in MLB’s top 100 young prospects. While many see Duran as a key clubhouse player, he is the best option for the Sox to trade for a top pitcher. A deal with the Minnesota Twins for top starting pitcher Joe Ryan seems like a must. The Sox would likely have to give up García, Duran, and a pitching prospect for Ryan, who is under team control until 2028, which likely is the full scope of the Sox’s World Series contention window. 

So, let’s review. The Sox desperately need starting pitching — offseason signings of Dylan Cease and a trade with the Twins for Joe Ryan would create an effective three-headed monster in the pitching rotation. Not only that, prospect Connelly Early could fit in well in the No. 4 starting role, giving the Sox extra depth. With pitching out of the way, the Sox can then focus on signing Alex Bregman and Pete Alonso to medium-term deals to help anchor the Sox’s relatively young core. Players like Ceddane Rafaela, Wilyer Abreu, and Marcelo Mayer — who all had great seasons at their respective positions — need help settling into high-leverage environments like the playoffs. 

2026 looks like it will shape up to be an exciting year for the Red Sox. With the right offseason moves, they have a great chance to make a deep playoff run. The only question now is: what will ownership actually do to help this team?