Early life

Cashman was born in Rockville Centre, New York, and raised in Washingtonville, New York. He was raised in an Irish Catholic family, as the middle of five children born to Nancy and John Cashman.

The Cashman family moved to Lexington, Kentucky, where his father managed Castleton Farm, raising standardbreds for harness racing. Cashman described moving out of Washingtonville before starting high school as "the best thing to happen to, to get out of there." He attended Lexington Catholic High School before moving to the Washington, D.C., metropolitan area. He graduated from Georgetown Preparatory School in 1985. Cashman played baseball and junior varsity basketball at both schools, and added football in his senior year.

The Catholic University of America offered Cashman the opportunity to play college baseball for the Catholic Cardinals, competing in the National Collegiate Athletic Association's Division III, guaranteeing him playing time as a freshman. He was a four-year starter at second base and the team's leadoff hitter. He set a school record for most hits in a season, which has since been broken. He earned a bachelor's degree with a major in history in 1989.

New York Yankees (1986-present)

Yankees' owner George Steinbrenner met Cashman's father while John Cashman managed Pompano Park in Pompano Beach, Florida, and the two became friends. Cashman started with the New York Yankees organization as an intern in 1986. After he graduated from Catholic, the Yankees offered Cashman a position as a baseball operations assistant, which he accepted.

Steinbrenner was banned from baseball in July 1990 for hiring a gambler to investigate Dave Winfield. Gene Michael, then the Yankees' General Manager, took over daily operations of the Yankees, and Cashman assisted him. Michael named Cashman an Assistant General Manager in 1992.

General Manager (1998-present)

In February 1998, Cashman was named Senior Vice-President and General Manager, succeeding Bob Watson. He agreed to a one-year contract for $300,000, and became the second-youngest General Manager in MLB history. The Yankees won 114 games during the 1998 season, and won the 1998 World Series. In 1999, Cashman traded fan favorite David Wells to the Toronto Blue Jays to acquire Roger Clemens. The next year, he acquired David Justice, who won the American League Championship Series (ALCS) Most Valuable Player Award for his play in the 2000 ALCS. The Yankees won the 2000 World Series, making Cashman the first General Manager to win World Series titles in his first three years. In 2004, Cashman arranged the trade of Alfonso Soriano for Alex Rodriguez.

Despite the team's success, Cashman considered leaving the Yankees in 2005 due to conflicts with Steinbrenner and organizational disputes between team officials in New York City and Tampa, Florida. The Washington Nationals were rumored to be interested in hiring Cashman, which would have brought him back to the city where he attended school. 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.

With the increased authority, Cashman created a department of professional scouting, and tabbed Billy Eppler as its director. On September 30, 2008, Cashman signed a three-year contract to stay with the Yankees through the 2011 season. Following that 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. These three players played a significant role in the 2009 Yankees season, culminating with a victory in the 2009 World Series.

In 2010, Cashman held a hard line with Derek Jeter during contract negotiations, reportedly telling Jeter that he would prefer to have Troy Tulowitzki as the Yankees' starting shortstop. However, Yankees ownership agreed to sign Rafael Soriano in January 2011 without Cashman's approval. Cashman stated at the Soriano's introductory press conference that he disagreed with the deal. The Yankees re-signed Cashman to a three-year contract in November 2011.

During 2013, Rodriguez composed a tweet saying that he cleared to play by his doctors after his hip surgery. Cashman claimed that the doctors did not give such authority to clear Rodriguez to play after seeking a second opinion with them, and that Rodriguez should "shut the fuck up". After the 2013 season, the Yankees signed Masahiro Tanaka, Jacoby Ellsbury, Brian McCann, and Carlos Beltrán to contracts that totaled $438 million. However, the Yankees missed the playoffs for the second consecutive year. On October 10, 2014, the Yankees signed Cashman to another three-year deal through the 2017 season. That offseason, Cashman prioritized restructuring the Yankees roster with younger players. He replaced the retired Jeter with Didi Gregorius and acquired Nathan Eovaldi, both of whom improved during the season.

During Cashman's tenure as Assistant GM and VP/General Manager, the Yankees have won seven American League pennants and five World Series championships.

Honors

Cashman was selected As Major League Baseball Executive of the Year for 2009 by the Boston Chapter of the Baseball Writers' Association of America. Cashman was named to Crain's New York Business 40 under 40 list for 1999.

Cashman was also involved in the developing of the video game MLB Front Office Manager.

Personal life

Cashman lives in Darien, Connecticut. Cashman's wife, Mary, filed for divorce in February 2012; they had been reportedly separated for a year. The day prior, prosecutors charged a woman with stalking Cashman in an attempt to extort money regarding an extramarital affair. Cashman is a Kentucky Wildcats and New Jersey Devils fan.

Cashman has referred to himself as an "adrenaline junkie". In December 2010, Cashman rappelled from a 350-foot (110 m) building in Stamford, Connecticut, as part of an annual Stamford Christmas celebration. He jumped from an airplane with members of the United States Army Parachute Team to raise awareness for the Wounded Warrior Project, but broke his right fibula and dislocated his right ankle in the process. In November 2014, Cashman slept on a New York City sidewalk to raise awareness on behalf of homeless youth.

[ Source: Wikipedia ]