In the storied annals of baseball, few teams have endured as many gut-wrenching trades as the Boston Red Sox. Over their 125-year legacy, the Sox have pulled off deals that still haunt fans to this day—none more infamous than the 1920 cash-only swap that shipped a young phenom named Babe Ruth to the rival New York Yankees. That blunder didn’t just alter the Red Sox’s fate; it reshaped the entire sport, cursing Boston with decades of heartache.
Fast-forward to 1972, and the wounds reopened with another Yankee fiasco. Boston acquired the underwhelming 32-year-old first baseman Danny Cater, only to surrender 26-year-old reliever Sparky Lyle in return. Lyle exploded in pinstripes, topping the American League in saves with 35 in his debut season and 23 more in 1976. He anchored the Yankees to World Series glory in 1977 and 1978, even snagging the AL Cy Young Award in ’77—the second reliever ever to claim the honor. Ouch.
The ’90s brought more regret: At the 1990 trade deadline, the Red Sox flipped 22-year-old prospect Jeff Bagwell to the Houston Astros for reliever Larry Andersen. Bagwell blossomed into a Hall of Famer, while Andersen tossed just 22 innings over 15 games before bolting in free agency to the San Diego Padres. Another swing and a miss for Boston.
But for today’s Red Sox faithful, nothing cuts deeper than the February 12, 2020, blockbuster that exiled superstar outfielder Mookie Betts—fresh off an AL MVP award and a 2018 World Series triumph—to the Los Angeles Dodgers. Starting pitcher David Price tagged along in the deal, leaving fans reeling from the loss of a homegrown hero.
In exchange? Three prospects: Outfielder Alex Verdugo, who was cut loose by the Atlanta Braves in July and remains unsigned; infielder Jeter Downs, who suited up for just 14 games with Boston in 2022 before heading overseas to the Fukuoka SoftBank Hawks in Japan’s Pacific League; and catcher Connor Wong, the lone survivor clinging to the Red Sox roster.
Nearly six years later, Wong stood as the final thread connecting Boston to that fateful trade. With the non-tender deadline looming on Friday—when teams must decide on contracts for arbitration-eligible players—the Red Sox faced a pivotal choice: Keep Wong for another season or sever the last tie to the Betts era?
The drama peaked early. On Thursday, Boston dropped the bombshell: They’ve locked in Wong with a fresh one-year contract. As reported by MassLive’s Chris Cotillo, the deal guarantees $1.4 million, with up to $75,000 in performance bonuses—a hefty bump from his $790,000 salary this past season, per Spotrac. Yet, it’s a tad shy of the $1.7 million projected by MLB Trade Rumors’ arbitration formula.
Wong’s 2025 season was a tale of grit amid adversity. The 29-year-old, originally drafted in the third round by the Dodgers in 2017, battled through a nagging right-hand injury that culminated in surgery on October 9. It undeniably hampered his output, resulting in a dismal .500 OPS, zero home runs, and just 32 hits across 168 at-bats. Still, his defensive prowess behind the plate and flashes of potential have earned him this second chance.
As the dust settles, Red Sox Nation is left pondering: Is this the dawn of redemption for Wong, or just another chapter in Boston’s long saga of trade regrets? One thing’s certain—the Mookie Betts mega-deal’s echoes linger, but with Wong’s return, the story isn’t over yet. Stay tuned, Sox fans; baseball’s twists are endless.