The Boston Red Sox, after another early exit from the playoffs at the Wild Card stage, are looking to retool for a deeper run in 2027. But how active chief baseball officer Craig Breslow will be on the trade market hangs as an unresolved question for Red Sox Nation to obsess over for the next several months.
But the hosts of “Play Tessie” got a jump on Breslow Wednesday when, in the latest edition of their popular WEEI-affiliated podcast, they presented the Red Sox with a trade pitch that would help ease the team’s outfield logjam while bringing in a former second-round pick righthander and a three-time member of the 20-20 club.
What’s the trade pitch? As outlined by “Play Tessie” host Nat “Gordo” Gordon, Boston would land Oneil Cruz and Mitch Keller from the Pittsburgh Pirates for Jarren Duran and three other current members of the major league club. A prospect swap doesn’t figure into their proposed deal.
Cruz brings rare speed and power to a lineup that needs both, but the price includes left-handed starter Jake Bennett as well as Jarren Duran, and the hosts split on whether either club says yes.
Gordon built the deal for the show’s first “Who Says No” segment of the offseason. Boston would send Bennett, Duran, Mickey Gasper and Masataka Yoshida’s one-year, $18 million contract to the Pirates. His pitch rests on Cruz’s 2026 season.
“He hit 20 homers and stole 30 bags in 97 games,” Gordon said on WEEI’s Play Tessie podcast Wednesday.
Cruz, a 6-foot-7 left-handed hitter born Oct. 4, 1998, in Nizao, Dominican Republic, owns a career .243/.322/.438 line with 80 homers and 103 steals in 476 games since his 2021 debut. He hit .280/.368/.486 in 97 games in 2026, good for 2.8 WAR, and missed time with non-displaced fractures in the metacarpals of his left hand.
Keller, a 6-foot-3 right-hander born April 4, 1996, in Cedar Rapids, Iowa, was a second-round Pirates pick in 2014. He went 6-8 with a 5.29 ERA and a 1.37 WHIP over 115 2/3 innings in 22 starts this year amid shoulder issues. His career record stands at 48-73 with a 4.60 ERA. He signed a five-year, $77 million extension in 2024, leaving roughly $18 million for 2027 and $20 million for 2028.
Bennett, a 6-foot-6 lefty born Dec. 2, 2000, in Tulsa, Oklahoma, arrived from Washington for Luis Perales in December 2025 and debuted May 1. He went 9-7 with a 3.65 ERA and struck out 91 in 113 1/3 innings over 19 starts.
Duran, a speedy, 6-foot outfielder born Sept. 5, 1996, in Corona, California, and a 2018 Red Sox draft pick, made the 2024 All-Star team, and won the All-Star Game MVP award, while batting .285/.342/.492 with 21 homers and 34 steals. He slumped to .207/.266/.361 in 2026, with 20 homers and 21 steals in 151 games, and projects to earn about $11 million in arbitration.
Gasper, a 5-foot-9 switch-hitter born Oct. 11, 1995, in New Hampshire and drafted by the Yankees in 2018, hit .251/.357/.466 with 10 homers in 67 games.
Yoshida, born July 15, 1993, in Japan, signed a five-year, $90 million deal that expires after 2027. He batted .274/.347/.399 in 87 games this year.
Oneil Cruz’s Fit in the Boston Red Sox Lineup
Cruz saw fastballs on 49.5 percent of pitches during the best offensive season of his career, according to Gordon.
“Oneil Cruz is good at handling that velocity,” the podcaster said. Gordon identified high-velocity pitches as a Boston weakness, but cautioned that the sample covers roughly one season.
Co-host Pat Brown flagged the other side.
“He was first percentile in strikeout rate, second percentile in whiff rate. That’s adding a lot of downside with risk,” Brown said. Cruz posted a .676 OPS in 2025, and his .854 mark in 2026 sits well above his career .760.
Position is the larger question. Gordon ruled out shortstop and left the rest open. “Probably mostly an outfielder and a DH, but you’re getting him for the bat and what he can do for you offensively,” Gordon said.
Boston’s outfield already features Roman Anthony, Ceddanne Rafaela and Wilyer Abreu, and Rafaela, Abreu and third baseman Caleb Durbin all won 2026 Rawlings Gold Glove awards. Cruz’s defensive metrics in center field have been mixed to negative. “He was horrific at shortstop,” Pat said. Sammy saw third base as the best fit, but Durbin holds that job. The designated hitter spot is the opening, and Yoshida and Gasper, the players who fill it now, are the players leaving under the “Play Tessie” trade pitch.
The rotation takes a hit as well.
“If he’s in the deal, he takes the Jake Bennett slot,” Gordon said of Keller.
“Your rotation probably will be downgraded a bit,” co-host Sammy James added. Keller does not replace Sonny Gray either. Gray became a free agent in October after going 18-5 with a 2.72 ERA and 169 innings, against Keller’s 5.29 ERA.
Oneil Cruz Trade Verdict for Boston Red Sox and Pirates
The Pirates shed about $38 million in Keller money and absorb Yoshida’s $18 million, a savings of roughly $20 million, Gordon and James calculated. Duran’s $11 million arbitration figure and Cruz’s projected $7 million shrink that gap.
“For a Major League Baseball team, that’s not that much. But the Pirates are only technically a Major League Baseball team,” James quipped.
Brown sees Pittsburgh pulling the trigger.
“They are so strapped for cash that they would take the hit on a potential Oneil Cruz return just to free up a little bit of money,” he said. Brown sees Boston declining.
“You trade Yoshida, but you basically added a year of Yoshida,” Brown said.
James had both teams saying no, though barely for Pittsburgh.
“It’s very close to the Pirates taking it,” Sammy said. Gordon agreed and pointed to Boston’s preferences.
“If you brought this straight to their front offices, they would both say, ‘Thanks, but no thanks,'” Gordo said. He added that the Red Sox need “more certainty when it comes to the bat we’re adding.”
The financial result favors Pittsburgh. The Pirates move Keller’s 2028 salary, and Boston extends its commitment through that season while giving up Bennett’s 3.65 ERA and years of control. Boston keeps prospects such as Franklin Arias and Payton Tolle, the hosts noted, and still gets a single high-variance bat. The offense improves only if Cruz repeats 2026. The defense gains little.
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