By Jon VankinShareNewsweek is a Trust Project memberIn the three weeks since the offseason got underway, the Boston Red Sox have already lost four left-handers from their bullpen. Trade deadline pickup Steven Matz, who allowed just five earned runs in 21 2/3 innings down the stretch after being acquired, departed in free agency.
Fellow southpaws Chris Murphy and Brennan Bernardino were traded, to the Chicago White Sox and Colorado Rockies, respectively. And Justin Wilson, the first free agent signed by Boston after the 2024 season, became one of the first to declare free agency this year.
...The quartet of departures leave the Red Sox bullpen, at least for the moment, with closer Aroldis Chapman as the only left-handed option — though how the Red Sox plan to handle their No. 2 overall prospect Payton Tolle is not yet clear. The 6-foot-6, 250-pound left-hander started 18 of his 20 games across three minor league levels this year, and then started three more after his promotion to Fenway Park.
But the Red Sox then sent him to the bullpen for another five appearances, including one in the postseason.
With Tolle's role up in the air, the Red Sox have a glaring need for at least one left-handed reliever. Baseball analyst Griffey "G.G." Geiss, writing for the site Medium on Sunday, identified a "buy low option" who, despite likely needing to start next season on the injured list has "the ability to become your first non-Chapman lefty out of the pen," Geiss wrote. "NEED IT."
That pitcher is Cleveland Guardians 2014 fourth-round draft pick Sam Hentges. The Guardians non-tendered Hentges on Friday, making him an immediate free agent, after the lanky left missed the entire 2025 season recovering from shoulder surgery in September 2024.
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The 29-year-old also underwent arthroscopic knee surgery in September this year, requiring another four months of rehab.
Drafted out of Mounds View High School in Arden Hills, Minnesota, Hentges finally made it to the major leagues with Cleveland in 2021, throwing 206 2/3 innings over 168 games, all but 12 out of the bullpen. Hentges has not started a game since Aug. 26, 2021.
In his three seasons as a full-time bullpen arm, Hentges threw 138 innings with a solid 2.93 ERA, striking out 155 against just 42 walks and a 1.12 WHIP. His WHIP came in below 1.0 in two of his three bullpen seasons.
Listed at 6-foot-8, 245 pounds, Hentges achieves a reach of seven feet, according to statistics cited by Geiss, well above the MLB average of 6 feet, 4 inches, a trait that "makes him so intriguing, not to mention he generates plenty of ground balls and limits pull-side balls in the air," Geiss wrote.
Hentges' four-seam fastball averages 95 mph, according to Statcast, placing him in only 65th percentile of major league pitchers, though hitters perceive his pitches as somewhat faster due to his arm extension off the mound.
But his most frequently used pitch, 32 percent of all pitches thrown, is his curve ball, which Geiss called "nasty," and "one of the best in the entire game."
Before the Guardians declined to offer him a contract, Hentges was estimated by Spotrac to be expecting a $1.4 million salary in his third year of arbitration, making him a low-risk option for Red Sox chief baseball officer Craig Breslow to try, as he adds left-handers to the Boston bullpen this offseason.
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