The New York Yankees’ offseason is shaping up to be a masterclass in missed opportunities, as highlighted by Randy Miller and Bob Klapisch of NJ.com on Thursday. While the Bronx Bombers have tinkered with minor moves, they’ve struck out spectacularly on landing big-name free agents like four-time All-Star Kyle Tucker, three-time All-Star Bo Bichette, or even their own 29-homer slugger from last season, Cody Bellinger.

Cody Bellinger dealt troubling news in MLB free agency after Yankees report

Bellinger, fresh off a solid 2025 campaign with the Yankees, appeared to be GM Brian Cashman’s prime target. According to a Thursday report from The Athletic, the team dangled a multi-year deal with an average annual value exceeding $30 million—positioning him as the fifth-highest-paid outfielder annually, despite his eighth-ranked OPS among outfielders last year. However, Bellinger is digging in for at least a seven-year commitment, and the Yankees’ offer fell short on length, leaving negotiations in limbo.

Yankees’ Epic Fail: Letting a Rising Star Slip Away

But amid the Bellinger drama, the Yankees committed what could be Brian Cashman’s most egregious oversight in decades: quietly allowing 26-year-old outfielder Brennen Davis—a former top Cubs prospect with a scorching .975 OPS across three minor league levels in 2025—to walk into minor league free agency. Davis, who smashed 17 home runs in a mere 170 at-bats (one every 10 trips to the plate), has now signed with the Seattle Mariners on December 18, assigned to their Triple-A Tacoma Rainiers. The move wasn’t even reported publicly until this week, underscoring how under-the-radar this blunder was.

For context, that’s a homer rate that outpaces elite talents: Last year’s No. 1 overall prospect Roman Anthony hit one every 22.2 at-bats in his final minor league stretch before joining the Boston Red Sox, while Yankees legend Aaron Judge managed one every 18.5 at-bats in his 2016 minor league finale.

Brennen Davis: From Top-15 Phenom to Forgotten Gem

Drafted in the second round by the Chicago Cubs in 2018 out of Basha High School in Chandler, Arizona, Davis skyrocketed to No. 15 overall in MLB Pipeline’s 2023 rankings and No. 3 in the Cubs’ system—solidly a top-5 prospect within one of baseball’s deepest farms. At just 26, he’s still primed for growth, boasting a career .792 OPS in the minors.

Yet, a barrage of injuries—back and core surgeries, additional back issues, multiple concussions, and a brutal ankle fracture—derailed his trajectory, sidelining him for chunks of seasons since 2019 (excluding the 2020 COVID shutdown). The Cubs DFA’d him in November 2024, and the Yankees scooped him up in December, only to watch him stage a remarkable 2025 resurgence.

Why on earth did Cashman let this potential star escape? Despite Davis’s breakout performance, the Yankees showed zero interest in retaining him, allowing him to hit free agency. Now, Seattle gets a high-upside outfielder who could soon crack the majors, while the Yankees’ outfield depth takes a needless hit. In an offseason already plagued by inaction, this whiff might haunt the Bronx for years—a once-in-a-century Cashman clunker that fans won’t soon forget.