In the recent weeks, the world of Major League Baseball has been buzzing with multiple high-profile players securing lengthy extensions as the regular playing season initiated. The crowning jewel among these was the Boston Red Sox’s landmark agreement of a six-year, $170 million deal with their primary pitcher, Garrett Crochet. It is particularly worth noting that these extension agreements neither occur in isolation nor are they devoid of future implications. Let’s delve deeper into these recent agreements to decipher how they are reflective of the present market trajectory and their potential to shape the contract negotiations of corresponding players.
Garrett Crochet’s prematurity paid off. When Boston Red Sox navigated a trade with the Chicago White Sox to acquire Crochet, the signal was quite clear: they had a substantial interest in the pitcher that extended beyond his remaining two season tenure. Crochet had already expressed desires for an extension the previous summer, hence, the likelihood of this contract extension was high. The prophecy is now realized.
Previously, in the summer and then again in the spring, I had predicted Crochet’s extension to span five years worth $110 million. While this might appear as a justification, the southpaw’s recent deal with Boston aligns almost perfectly with this prediction. My initial estimates had factored in Crochet’s $3.8 million wage for the current season while the agreed extension kicks in from 2026.
Initially, I had envisioned the Red Sox cashing in on three years of Crochet’s free agency for $32 million each; however, they secured five years of his agency at an equal rate with a strategic opt-out after the season of 2029. Crochet’s relative youth, ripe to hit free agency just ahead of his age-28 season in 2027, undoubtedly instilled confidence in Boston to invest in the longer deal. The valuation of $32 million for Crochet, following a sturdy season, bodes well for other starting pitchers eyeing the extension market.
Earlier in spring, I valued the free-agent years of pitchers like Tarik Skubal, Logan Gilbert, and George Kirby at $35 million, $30 million, and $30 million respectively. Skubal, with arguably a stronger record than Crochet to date, and Gilbert and Kirby, possessing more documented careers, albeit being further from free agency, could cite Crochet’s valuation as a base standard for their long-term contract discussions.
The contract extensions signed by Tanner Bibee (five years, $48 million) and Brandon Pfaadt (five years, $45 million), fit conveniently into a broader sphere of agreements for pitchers of similar calibre. Free agency awaited Hunter Greene, Brayan Bello, and Pfaadt in five years when they signed their deals. The negotiations, although, postponed Pfaadt’s extension until 2026 akin to Crochet’s.
These agreements provide for a single year of free agency within the $22 million to $25 million range and uniformly contain an exclusive option for the club to extend at $21 million. Considering Bibee’s pending free agency was a year earlier and his record boasted of two good seasons, it’s slightly surprising that his inclusion in this group aligns as fittingly as it does. After sanding a season with 3 WAR or more according to FanGraphs, he contracted for a price lower than Greene.
This group of pitchers with similar contract scenarios might eventually welcome Spencer Schwellenbach, Spencer Arrighetti, Simeon Woods Richardson, Bryce Miller, Bryan Woo, and Andrew Abbott. The apparent impending evolution of the catcher market led me to advise Adley Rutschman and William Contreras against signing extensions. The initial extension among these two and Cal Raleigh, who all entered the arbitration process with matching price tags last winter, would establish the minimum negotiation standard for the remaining duo.
Veteran catcher J.T. Realmuto’s impending free agency at the end of this season and a potential short-term, higher-AAV contract could propel the catcher market. Raleigh’s agreement of a six-year, $105 million contract extension with Seattle, is quite fitting for the dependable catcher.
Previously, while evaluating potential extensions for Contreras and Rutschman, I had noted the salary cap of the second tier of catchers at approximately a $23 million yearly wage. Raleigh’s agreement comprises three years of team control, with his arbitration earnings estimated at around $30 million across these seasons, and buys out three free-agent years at approximately $25 million yearly. This contract reflects a slight market progression, and we can expect Contreras and Rutschman to further pioneer the upward trend.
The imminent changes in the catching market majorly justify Toronto’s contract extension for Alejandro Kirk spanning five years for $58 million. Kirk’s deal, kicking off in 2026, secures four free-agent years for an estimated total of about $50 million, breaking down to $12.5 million per annum.
Although Kirk does not match Raleigh, Contreras, and Rutschman’s standards – earning less in his second arbitration year than what the others earned in their first – he could have arguably negotiated a slightly more lucrative contract had it come after Raleigh’s extension. However, given Kirk’s defensive strengths especially his exceptional pitch framing, which could potentially be edged out with the anticipated introduction of a ball-strike challenge infrastructure, the locking in of long-term earnings at the present moment makes sense.
Kirk’s agreement could potentially set a benchmark for catchers of the next rung such as Ryan Jeffers of Minnesota or Shea Langeliers of the Athletics.