Remember when Torpedo bats were all the rage? Yawn. That was so March.
Welcome to April. Welcome to extension season.
Tuesday, Garrett Crochet ¨C who had set an Opening Day deadline for any extension talks ¨C agreed to a six-year, $170 million extension with the Red Sox, who followed that up Wednesday with an eight-year, $60 million extension for rookie Kristian Campbell.
Jackson Merrill also hopped on the extension train Wednesday, signing a nine-year, $135 million deal to remain with the Padres through the 2034 season.
What happened to players not wanting to negotiate during the season?
¡°I wouldn¡¯t view these as ¡®in-season¡¯ deals,'¡± a National League executive said. ¡°Clearly both of them started during Spring Training and they got close enough that both sides decided to give it a small amount of additional time. When 90% of the work is done during the offseason, you see these bleed into the regular season sometimes. It also happens with lots of the deals that don¡¯t get done.¡±
Mariners catcher Cal Raleigh (six years, $105 million) and Athletics outfielder Lawrence Butler (seven years, $65.5 million) inked extensions during Spring Training, bringing the total to five extensions in the past month alone. Wednesday, second baseman Ketel Marte and the D-backs agreed to a restructuring of his current deal that will keep him in Arizona through at least 2030, though because he was signed through 2027, he falls into a separate category than the rest.
Four of the five extended players were at least three seasons away from free agency, so their clubs bought out all of their remaining arbitration years in addition to some free-agent years. Only Crochet ¨C who was closest to free agency with only two years of club control remaining ¨C had set an Opening Day deadline to get an extension done.
Yet a few days after Boston¡¯s opener, a deal got done. So much for deadlines.
¡°I¡¯m sure these were talks going back a few months,¡± an American League executive said. ¡°Overall I am a firm believer that deadlines are good since both parties are working toward a finish line that¡¯s defined. Maybe that deal just had to go into extra innings to get completed.¡±
An NL executive whose club signed a player to an extension during the first week of a recent season recalled working around a similar Opening Day ¡°deadline,¡± eventually consummating the deal days after the season had started.
¡°In my experience, that usually happens because the talks started during the spring and just didn¡¯t get wrapped up, but there was momentum so neither side wanted to shut it down,¡± the exec said. ¡°I think as long as the talk gets started and there is clearly motivation on both sides to figure something out, they tend to continue past any ¡®deadline.¡¯¡±
Which brings us to the most fascinating extension candidate of 2025: Vladimir Guerrero Jr.
If we are to believe Guerrero, who set a mid-February deadline for contract talks, the Blue Jays missed their window to extend him once the first pitch of 2025 was thrown. But what if Toronto approached his agents with a Godfather offer ¨C i.e., one he couldn¡¯t refuse?
One agent noted that such deadlines often mean ¡°no negotiation,¡± though if a club extends an offer, the agent has a fiduciary duty to take that to his or her client.
¡°If there have been zero talks, I would tell a team that approached me now, even if we didn¡¯t set a deadline, that I will not engage in conversations,¡± the agent said.
¡°If they want to simply make an offer, I will review and discuss with my client, but any offer will either get done or not get done in one conversation. If you truly want to make an attempt, come with what you¡¯ve got right away. My client will not have this on his mind for more than a few hours. And I mean that.¡±
¡°Every player and agency is different,¡± said an NL executive. ¡°Usually [any talks after Opening Day] have to start with being close enough for the distraction to be worth it.¡±
Another agent said he does not believe in imposing such soft deadlines, as both sides know there is nothing firm or binding about them.
¡°This has been passed down from player to player as the thing to do to try to exert leverage,¡± the agent said. ¡°It¡¯s dumb.¡±
Unlike free agency, players considering an extension aren¡¯t shuttling around from city to city, taking time-consuming meetings with interested clubs. Their involvement in such talks typically consists of hearing the offer, discussing the pros and cons with their agent, then making a yes or no decision. Veteran players might get a little more involved in such talks, which is why they tend to be the ones to impose such deadlines.
¡°In reality, everything in baseball ¨C everything ¨C only happens where there is a deadline,¡± the first agent said, citing hard deadlines such as the arbitration exchange date, the Trade Deadline and the expiration of the collective bargaining agreement. ¡°[Extension] deadlines typically are very soft and are meant to pressure teams publicly. Most teams monitor the media and social media and are very aware of fan and media perception, so these deadlines do impact teams, at least emotionally. But are players going to ignore offers if they are very big?¡±
Despite the presence of Opening Day deadlines, some teams will continue to try coming to a deal in conversations with the agent.
¡°It depends on the nature of the relationship between the team, agent and player,¡± an NL executive said. ¡°Sometimes one side has little choice but to impose a hard deadline in order to spur constructive dialogue. In other situations, the relationship between the parties is strong enough to have open and honest conversations right from the start. There are no hard feelings if one side receives a polite ¡®No, thank you¡¯ early on in the process.¡±
The history of players entering their contract years agreeing to an extension once the season has started suggests that Guerrero will indeed test free agency.
Mookie Betts agreed to his 12-year, $365 million deal on the day before the delayed season-opener in 2020, while Rafael Devers signed his 11-year, $331 million extension with the Red Sox in January 2023 as he prepared to enter his contract year. Other would-be free agents including Aaron Judge, Xander Bogaerts and Carlos Correa held to their self-imposed Opening Day deadlines, testing the free-agent market after the season in each case.
Matt Chapman was one of the few outliers in this category, agreeing to a six-year, $151 million deal last September, roughly one month before he was eligible to opt out of the three-year, $54 million deal he had signed prior to the season.
¡°Is it possible Vlad signs a deal before the end of the year? Absolutely,¡± an AL executive said. ¡°Toronto seems motivated to get something done, but it¡¯s going to take a big offer to get him locked up this close to free agency, especially after he imposed that deadline. Like anything else, it will be about the money.¡±