During Cashman's tenure as general manager, he inherited a core that was built by Gene Michael and Bob Watson and the Yankees have won seven American League pennants and four World Series championships.

He was named assistant general manager in 1992, helping to run the team while owner George Steinbrenner was suspended from baseball.

[4] He became a baseball fan at a young age, attending a summer camp hosted by Bucky Dent before starting high school.

[3][6] The Cashman family moved to Lexington, Kentucky, where his father managed Castleton Farm, raising standardbreds for harness racing.

Cashman played baseball and junior varsity basketball at both schools, and added football in his senior year.

In 1999, Cashman traded fan favorite David Wells to the Toronto Blue Jays to acquire Roger Clemens.

Instead, Cashman agreed to a new contract with the Yankees following the conclusion of the 2005 season which gave him more authority in personnel decisions and paid him an average of $1.3 million more over the following three years.

[18] With the increased authority, Cashman created a department of professional scouting, and tabbed Billy Eppler as its director.

[21] Following the 2008 season, when the Yankees failed to make the playoffs, Cashman signed CC Sabathia, A. J. Burnett, and Mark Teixeira to long-term free agent contracts and traded for Nick Swisher.

[27] After the 2013 season, the Yankees signed Masahiro Tanaka, Jacoby Ellsbury, Brian McCann, and Carlos Beltrán to contracts that totaled $438 million.

[30] In the 2016 season, he traded Carlos Beltrán to the Texas Rangers, Andrew Miller to the Cleveland Indians, and Aroldis Chapman to the eventual World Series Champion Chicago Cubs to bolster the Yankees farm system.

Making their first appearance in the American League Championship Series since 2012, the Yankees lost to the Houston Astros in seven games, far outpacing the expectations of many analysts.

Despite a lopsided victory in the AL Wildcard game over the A's, New York would fall to their rivals: Boston Red Sox in the Division Series.

The team finished both August and September 14–13, which included a 1–7 stretch against the Baltimore Orioles, Toronto Blue Jays, Tampa Bay Rays, and New York Mets, before an 11–2 run, and finished the season 33–27, good for second-place in the East and a spot in the American League Wild Card Series, their 28th consecutive winning season.

Numerous player injuries in the first half of the season contributed to poor offense (through July, the Yankees had the second-lowest number of runs scored in the A.L.).

Looking to bolster offensive production, Cashman traded for Anthony Rizzo and Joey Gallo, two strong left-handed batters.

[43] The Boston chapter of the Baseball Writers' Association of America selected Cashman as their MLB Executive of the Year for 2009.

The day prior, prosecutors charged a woman with stalking Cashman in an attempt to extort money regarding an extramarital affair.

[51] He jumped from an airplane with members of the United States Army Parachute Team to raise awareness for the Wounded Warrior Project and broke his right fibula and dislocated his right ankle in the process.

[52] In November 2014, Cashman slept on a New York City sidewalk to raise awareness on behalf of homeless youth.