Red Sox tabbed to deal top prospect, Jarren Duran for Cy Young lefty

Last December, the Boston Red Sox pulled off arguably the best trade of the offseason when they sent four of their top prospects — including catcher Kyle Teel, ranked No. 4 in their farm system — to the Chicago White Sox for lefty ace Garret Crochet.

The bold move paid off. Crochet won 18 games, with 2.59 ERA, led MLB in strikeouts with 255, and also pitched 7 2/3 innings allowing just one run in Boston’s lone postseason victory.

Could chief baseball officer Craig Breslow pull off another, similar blockbuster this time around?

The Red Sox podcast “Baseball Isn’t Boring” had a proposal for one on Tuesday — a massive trade that would send more shockwaves through MLB by bringing in 2024 American League Cy Young Award winner, and this year’s favorite, Tarik Skubal of the Detroit Tigers.

The catch, of course, is that Skubal has only one year remaining before he hits free agency. According to projections arrived at by the MLB Trade Rumors mathematical formula, the 28-year-old left-hander is expected to make $17.8 million next year — a significant hike over his $10.15 million 2025 salary.

To make the trade worthwhile, the Red Sox would likely want to sign Skubal to a contract extension. Given that the lefty is expected to become the first pitcher to haul in a $400 million long-term contract in free agency, the Red Sox would need to offer at least that sum in an extension.

Given those factors, what would the Red Sox need to give up to get Skubal, even for one season?

The trade, as proposed by podcaster Nat Gordon, who also hosts the Red Sox podcast “Play Tessie,” would send outfielder Jarren Duran — the subject of frequent Red Sox trade speculation — along with 2025 first-round draft pick, 15th overall, Kyson Witherspoon, to Detroit.

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Witherspoon, who turned 21 in August, was rated as the No. 10 draft prospect by MLB Pipeline, and the second-ranked right-handed pitcher. The former Oklahoma Sooners standout throws a fastball that tops out at 99 mph and is currently ranked No. 4 in the Red Sox farm system.

However, Gordon noted, the Tigers would ask even more of the Red Sox in order to give up Skubal, even for one season.

“If you’re the Tigers, you can’t make a deal like this if it doesn’t include a legitimate minimum potential of a mid- rotation starter coming back,” Gordon said on Tuesday’s “Baseball Isn’t Boring” podcast. “A guy who’s ready right now at the big league level.”

That guy, according to Gordon, is 23-year-old Connolly Early, who came up from Triple-A for four big league starts in September — and then received a baptism of fire when he was thrown in to start the third and deciding game of the AL Wild Card series against the Yankees.

“The reason I know it it could work is because I’m feeling the pain of trading three years of Jarren Duran, six years of Connelly Early and and your first round pick who you haven’t even seen touch touch a pro field yet,” Gordon continued. “He could be anything. He could even be Tarik Skubal.”

“Baseball Isn’t Boring” host Rob Bradford, a veteran Red Sox correspondent for WEEI.com, gave his seal of approval to the trade idea.

“If you get Tarik Skubal and — with the assumption that you’re going to do whatever it takes to sign him like you just did like with Garrett Crochet — if you do that, you get those two guys,” Bradford said, “what you have done is that you have set yourself up undeniably for the next five years to basically be the favorites in the American League.”

Early in the season, the Red Sox signed Crochet to a six-year extension for $170 million — but that, in all likelihood, is only a fraction of what it would take to retain Skubal beyond 2026.

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