The Boston Red Sox made a massive gamble ahead of the trade deadline, sending a massive haul of prospects to the Baltimore Orioles in exchange for three-time All-Star catcher Adley Rutschman. After underperforming in 32 games with Boston, Rutschman now enters his final year of salary arbitration. But the Red Sox face a tough decision on whether to try to extend Rutschman ahead of the 2027 season. 

Here’s what a potential extension could look like: 

Prior to being traded to Boston, Rutschman had exploratory talks with Baltimore about a potential extension. “Rutschman, then, would probably want a deal that makes him a lifetime Oriole, or close to it,” wrote The Athletic’s Ken Rosenthal on July 6. “His benchmark might be the nine-year, $167 million extension Buster Posey signed with the San Francisco Giants in March 2013,” he continued. 

The idea that Rutschman could be in line for a deal like Posey's, who will almost assuredly be in Cooperstown in the near future, is a bit far-fetched. Prior to signing that deal, Posey posted a career slash line of .314/.380/.503/.883 with 46 home runs and 191 RBI, winning the 2010 National League Rookie of the Year award, the 2012 National League Most Valuable Player award, and two World Series titles. A far cry from Rutschman’s .252/.339/.414/.753 with 74 home runs and 290 RBI, with a career accolade list of three All-Star appearances. 

Catchers typically struggle to capitalize on their value given the high injury risk from the wear and tear of being behind the plate nightly. Rutschman is no stranger to those concerns, having played just 189 games over the last two seasons. 

Beyond Rutschman's worse resume than Posey's, the Red Sox have shied away from deals that take players well into their 30s, with the longest deal in recent memory being the eight-year extension given to Roman Anthony, which takes him through his age-29 season. 

With Posey’s nine-year deal seemingly out the window, we’ll have to look at some more recent catcher deals, which… gets complicated, to say the least. Of the five richest deals signed by catchers, only one was signed with one year of service time remaining: Toronto Blue Jays’ Alejandro Kirk. So let’s start there: 

Ahead of the 2026 season, Kirk signed a five-year, $58-million deal to remain in Toronto through 2030. Before signing, Kirk was a two-time All-Star with a career line of .268/.345/.398/.743. Like Rutschman, Kirk is a strong defensive catcher when it comes to blocking balls in the dirt and framing. However, he struggles to throw runners out. 

Though an average annual value of $11.6 million feels low based on Rosenthal’s reporting, we’ll have to keep looking. 

At 29, Murphy signed a six-year, $73-million extension with the Atlanta Braves, buying out his final two years of arbitration. According to Spotrac, Murphy was paid $9 million in 2024, his penultimate arbitration year, and $15 million annually for the remainder of the deal. 

At the time of signing, Murphy posted a .240/.336/.441/.778 line with 67 home runs and 215 RBI, earning an All-Star selection and becoming one of the game’s best defensive catchers. 

The runner-up for the 2025 American League Most Valuable Player award, Raleigh signed a six-year, $105-million deal to remain with the Seattle Mariners through the 2030 season, buying out his final three arbitration years. In the four seasons leading up to his extension, Raleigh posted a line of .218/.296/.444/.740 with 93 home runs and 251 RBI. Defensively. Raleigh is a mixed bag, with improving blocking skills, but is middle of the road in both framing and throwing runners out. 

Raleigh's deal is also slightly different than the one Rutschman would be looking to sign. While his deal carries an AAV of $17.5 million, the number is lower because he's receiving a lower salary in what would have been his arbitration years. Beginning in 2028, Raleigh will be paid $24.6 million annually. 

Will Smith of the Los Angeles Dodgers has the richest catcher contract (by total value). Smith signed a 10-year, $140-million extension with Los Angeles ahead of the 2024 season, buying out his final two arbitration years. However, in typical Dodgers fashion, Smith will be paid $5 million annually from 2034-2043 in deferred payments, lowering the luxury tax hit to just $12 million annually. The deferred payments, expected to be a hot-button topic in ongoing labor talks, paired with Smith being paid through his age-38 season, make the comparison a bit far-fetched. 

Before signing the deal, Smith hit .261/.357/.483/.840 with 91 home runs and 306 RBI over five seasons, while providing slightly above-average defense behind the plate. 

Projecting contracts is an imperfect science. From a strictly production standpoint, Rutschman is most similar to Murphy or Kirk. However, neither player dealt with the same injury problems as Rutschman in the seasons leading up to their extensions. Murphy also represents the closest fit defensively to Rutschman, profiling as one of the best defensive catchers in the sport. The $15 million AAV Murphy would earn from 2025 through 2028 would seem to be the floor of what Rutschman would look for in a potential deal. With MLB Trade Rumors projecting Rutschman to make $9 million in arbitration in 2027, could the Red Sox bump that number up slightly to lower the value of the remainder of the deal to, say, $11 million in 2027 and $14-15 million each year after? 

Then, of course, comes the term: catchers especially struggle to cash in on the open market later in their careers. Philadelphia Phillies backstop JT Realmuto posted a line of .257/.315/.384/.700 in 134 games in 2025 before hitting the open market ahead of his age-35 season. Realmuto sat on the free-agent market until Jan. 20, when he signed a three-year, $45-million extension to return to Philadelphia, a move widely criticized as an overpay for a catcher his age.  

Red Sox Chief Baseball Officer Craig Breslow will have to get creative to find common ground with Rutschman. A six-year contract would take him through his age-34 season, having him hit the market at a rather inopportune time. One possible solution for the Red Sox to give Rutschman the long-term commitment he's reportedly seeking could be to front-load the deal, paying him more in his prime while paying him incrementally less as he ages, reducing the franchise's financial burden as he ages and presumably declines.