Chicago White Sox lefty Garrett Crochet could be on the trade market and the Red Sox might be interested, but acquiring him won’t be easy. Duane Burleson/Associated Press

MLB free agency is finally heating up. Here’s a few questions facing the Boston Red Sox:

1. Is Garrett Crochet worth one of Boston’s “Big Four” top prospects?

The Red Sox would have to give up a lot, possibly even one of their “Big Four” prospects – Roman Anthony, Kristian Campbell, Kyle Teel or Marcelo Mayer – in order to acquire White Sox left-hander Garrett Crochet’s last two years of club control.

Is the southpaw from the South Side worth the risk? This was his first year in the starting rotation, and his 146 innings are exactly double the number of innings he pitched previously. Not single-season total. Career total.

Crochet’s trade deadline strategy could also indicate his personality may not be a fit for Boston. Hurtling toward breaking MLB’s modern single-season loss record, the White Sox dealt away several players this summer. It looked like Crochet would be one of them before his comments about wanting a contract extension in order to pitch in the postseason threw off prospective trade partners. Crochet also made it clear that he didn’t want to pitch out of the bullpen again, something many starters do to help their teams get through the postseason. He cited health concerns in regards to both of his desired terms.

White Sox GM Chris Getz told ESPN that he was “a little surprised and taken aback” by the situation, saying “That’s not exactly the tactic I would have taken, being a former player.” Such boldness wouldn’t endear an unproven pitcher to a more demanding fan base such as Boston’s, either.

Perhaps the risk isn’t worth one of the “Big Four.” Or perhaps it’s the other way around. Trading proven talent for potential is often a lopsided exchange, because the shelf-life of a top prospect is short. Approximately 10% of minor leaguers make it to the majors, and only a small fraction stick around long enough to reach free agency, much less command a big payday. The Red Sox were in this boat when they made a trade with the White Sox for Chris Sale in December 2016. Boston got an ace and another championship, and didn’t lose much in dealing away Yoan Moncada, Michael Kopech, Luis Basabe and Victor Díaz.

2. Is Roki Sasaki a fit for the Red Sox?

Hard-throwing Roki Sasaki, the 23-year-old Japanese star nicknamed “The Monster of the Reiwa Era,” could be one of the best pitchers of the next decade, and he’s being posted by his Nippon team, the Chiba Lotte Marines, in the coming weeks.

Among the many highlights on the right-hander’s resumé: a 105-pitch perfect game with 19 strikeouts (including 13 consecutively) when he was a 20-year-old rookie in April 2021. What’s more, he followed that performance with eight perfect innings in his next start.

Roki Sasaki will be posted by the Chiba Lotte Marines in the coming weeks, and the 23-year-old right-hander is expected to draw significant interest from major league teams. Eugene Hoshiko/Associated Press

He’s also one of the most affordable options on the market. Because he’s under 25, Sasaki still qualifies as an international amateur free agent, so unlike Yoshinobu Yamamoto, who received an unprecedented 12-year, $325 million deal from the Dodgers last offseason, Sasaki can only sign the contract of a debuting minor leaguer, which gives the team six years of contractual control (three making the MLB minimum followed by three arbitration).

Sasaki’s amateur status also subjects him to international bonus pool money restrictions. The Dodgers, Orioles, Yankees, Giants and Red Sox (in that order) have the five largest remaining international bonus pools for this year.

The Red Sox haven’t had a marquee ace atop their rotation since early in Sale’s time with the team. And one as affordable as Sasaki comes around about as often as Halley’s Comet.

3. Will the Red Sox extend Tanner Houck?

The two sides have discussed an extension at various points over the years, including last winter, but the price will certainly be higher now that Houck is an All-Star. He just finished his first 30-start season with a 3.12 ERA, the best single-season mark by a Sox pitcher over at least 30 starts since Sale’s first Boston campaign in 2017. Houck, 28, also led the American League with a 0.6 HR/9, allowing just 11 homers across 178 2/3 innings. The last Red Sox pitchers to make at least 30 starts and allow no more than 11 home runs were Roger Clemens in 1990 and 1992, and Willard Nixon in 1955.

Red Sox starting pitcher Tanner Houck had the best season of his career in 2024, making the All-Star team for the first time. Paul Sancya/Associated Press

“I’m always open to (extension) conversations. I love Boston,” Houck told the Boston Herald on the last day of the season. “My wife and I love it here. We’ve made this place kind of our second home.”

4. Why haven’t the Red Sox discussed an extension with Jarren Duran?

Earlier this fall, sources told the Boston Herald that the Red Sox have never discussed an extension with Duran.

Age and competition are factors in this decision. Though Duran only turned 28 on Sept. 5, there are several younger rising outfield stars in the organization. The Red Sox extended center fielder/shortstop Ceddanne Rafaela last spring, and he turned 24 on Sept. 18. Right fielder Wilyer Abreu, who just became the first Red Sox rookie to win a Gold Glove since Fred Lynn in 1975, doesn’t turn 26 until June 25. Top prospects Roman Anthony, 20, and Kristian Campbell, 22, also play the outfield.

5. Does Masataka Yoshida have a future with the Red Sox?

Yoshida is the expensive puzzle piece that doesn’t quite fit the big picture. Trading him makes a lot of sense, but finding him a new home will likely hinge on the Red Sox covering a significant portion of the $55.8 million he’s owed over the last three years of his contract. That they decided they didn’t want him playing defense after only one year in the majors doesn’t boost his trade candidacy, either, as it was a clear vote of no-confidence in his defensive abilities.

Injuries are another drawback. After missing over a month of the season because of a thumb injury, Yoshida is spending the offseason in Boston, working with the medical staff as he recovers from right shoulder surgery.

6. Will the Red Sox be willing to pay Max Fried?

Does Max Fried want to reunite with his high school teammate, Lucas Giolito, in Boston? It’s a moot point if the Sox are unwilling to pony up the cash: MLB Trade Rumors projects that Fried will command a six-year deal in the ballpark of $156 million. The Red Sox would also have to forfeit a draft pick, the penalty for signing a free agent who rejected a qualifying offer from their former club.