The clock is ticking for the Boston Red Sox and Garrett Crochet to strike a deal before Opening Day, and if they don’t, his price tag could explode. And there’s a catch too—Crochet has already made it clear that once the season starts, extension talks are off the table. That leaves Boston, who traded for him this offseason, with a tight window to get a deal done.

The 25-year-old left-hander, currently earning just $3.8 million in 2025, is at a career crossroads. This isn’t just about a nice raise—it’s about potentially breaking records. If Crochet delivers the season many expect, he could become the most coveted starting pitcher in baseball next winter. That’s why Boston faces a crucial decision: extend him now or risk losing him in a historic bidding war.

“If Crochet does what most people in baseball think he will do this season, his price tag will blow past every other starting pitcher in baseball,” Rob Bradford said this week. Crochet’s situation is rare. He started his career in the league as a relief pitcher for the White Sox before moving into a starting pitcher role in 2024. With his speed, impressive slider, and fluid pitching techniques he is shaping up to be a top-tier prospect.

On the flip side, Bradford also reflected on the team management’s perspective: “But from the Red Sox point of view, there is the opportunity to try and siphon some certainty by waiting out what would be Crochet’s second full season as a big league starter.” Regardless, Boston’s front office has a history of waiting too long on extensions, and it has backfired. Just ask Mookie Betts or Xander Bogaerts. Letting Crochet hit free agency could force the Red Sox into a bidding war with deep-pocketed rivals like the Dodgers, Mets, or Yankees—not exactly an ideal scenario.

Further, if Crochet dominates in 2025, his price tag could shatter expectations. We’re talking about a lefty with frontline stuff, entering free agency at just 25 years old—something MLB hasn’t seen in a long time. The top left-handed starters in recent years, like Carlos Rodón and Blake Snell, landed massive contracts despite injury concerns and being several years older than Crochet. If he pitches to his potential, he could command a deal that exceeds others, both in length and total value. But the deal-clinching factor for the Boston outfit still remains very much in the air.

The next eight days could define the Red Sox’s future. If they act now, they might secure an ace at a price that looks like a bargain in a few years. If they don’t? They’ll spend the season watching Crochet’s value soar—and hoping they don’t end up paying for it later.

The risk of waiting: Will Red Sox regret it?

The Red Sox have been burned before by waiting too long on extensions, and they can’t afford to make the same mistake with Garrett Crochet. Allowing Mookie Betts and Xander Bogaerts to enter free agency resulted in departures that forced the team to shift focus to damage control rather than nurturing their own talent at home base. If Boston fails to secure Crochet’s contract now, they might find themselves in a fierce bidding war, against wealthy teams like the Dodgers, Mets, or Yankees that they may not emerge victorious from. Also, his age and potential as an agent set him apart, resulting in his value surpassing the estimations.

Waiting might seem like the safer play, allowing the Red Sox to evaluate Crochet over a full season as a starter. But if he thrives, they’ll have zero leverage in negotiations. By next winter, he wouldn’t just be the best young starter available, he’d be a unicorn in free agency. At just 25 years old, Crochet could become the most valuable pitcher on the market, commanding a deal that dwarfs recent contracts given to elite lefties.

By then, Boston may be forced to choose between paying a record-breaking price or watching another star walk away. Do you think the Red Sox should make a move now or wait for him to prove himself?