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5 best and worst Yankees moves made by Brian Cashman, from acing Gerrit Cole signing to Sonny Gray debacle

PUBLISHED Oct 8, 2026, 7:15 AM ET

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Media Bias Meter

Sources: 44

Left 2%

Center 91%

Right 7%

Sources: 44

New York Yankees general manager Brian Cashman has overseen a complex tenure defined by both historic roster triumphs and high-profile acquisitions that failed to meet expectations. Among his most celebrated moves was securing elite starting pitcher Gerrit Cole via a landmark nine-year, $324 million contract in 2019, alongside drafting generational cornerstone Aaron Judge in 2013 and trading for dependable shortstop Didi Gregorius in 2014. Conversely, Cashman faced severe scrutiny for missteps such as the 2017 trade for right-hander Sonny Gray, who struggled under heavy media pressure in New York, and acquiring slugger Joey Gallo in 2021 before trading him a year later. These contrasting outcomes reflect the immense volatility of managing baseball operations in the Bronx, where massive financial commitments and intense fan expectations frequently amplify both personnel successes and high-stakes roster failures over multiple decades.

By Noormahi M. | JQJO News

Timeline of Events

On 2013-06-06 New York Yankees selected outfielder Aaron Judge in draft.
On 2013-12-03 New York Yankees signed outfielder Jacoby Ellsbury long term.
On 2014-12-05 New York Yankees acquired shortstop Didi Gregorius in trade.
On 2017-07-31 New York Yankees acquired starting pitcher Sonny Gray via trade.
On 2019-12-18 New York Yankees signed starting pitcher Gerrit Cole long term.
On 2021-07-29 New York Yankees acquired outfielder Joey Gallo via trade.
On 2022-08-02 New York Yankees acquired starting pitcher Frankie Montas via trade.
On 2026-10-08 analysts review historical front office tenure performance metrics nationwide.
On 2026-10-09 baseball observers evaluate strategic roster construction decisions across franchises.
On 2026-10-10 front office executives anticipate upcoming winter free agency decisions broadly.

News Intelligence

Immediate US impact: Baseball fans debate historical front office personnel decisions nationwide today.
Possible long-term US impact: Major league franchises adjust roster valuation models based on outcomes.
Most affected groups: New York Yankees supporters, baseball analysts, and sports media organizations.
Reader priority: Verify historical player statistics and official transaction records accurately.

Media Bias

Articles Published:: 44
Right Leaning:: 3
Left Leaning:: 1
Neutral:: 40
Distribution:: Left 2%, Center 91%, Right 7%

Explain Framing

Left: Focuses heavily on financial resource allocation disparities among major league teams. Center: Evaluates player performance metrics objectively against historical transaction costs and expectations. Right: Emphasizes intense fan expectations and traditional championship pressures in New York.