On February 3rd, 1998, Brian Cashman was officially named general manager of the New York Yankees. In the 23 seasons since, the Bronx Bombers have won 4 World Series, 6 American League pennants, and 13 AL East division titles. On the anniversary of Cashman taking over the helm, let’s take a look at five of the best moves he’s made as GM.

Cashman Lands Didi Gregorius from Arizona

In 2014, legendary shortstop Derek Jeter retired after a 20-year career in pinstripes. Obviously, whoever took over the position was going to have big shoes to fill. As in, massive shoes. As in, the most massive shoes possible.

The following offseason, the Yankees acquired Didi Gregorius from the Arizona Diamondbacks in a three-team trade. Arizona received Robbie Ray and minor-leaguer Domingo Leyba from the Tigers, and Detroit received Shane Greene from the Yankees.

In three seasons before the trade (one being an 8-game cup of coffee), Gregorius hit .243 with an OPS+ of 88. However, he flourished after coming to the Bronx. In 5 seasons with the Yankees, Didi hit .269 with an OPS+ of 101, and 97 home runs. He also received MVP votes in both 2017 and 2018.

Taking over the shortstop position from Derek Jeter is no easy task, to say the least. But Didi Gregorius did so with ease, emerging into a fantastic hitter and a lovable player, with his big smile and outgoing personality.

Trading Alfonso Soriano for Alex Rodriguez

Now, this wasn’t a one-for-one deal. But the full trade was still pretty simple: Alex Rodriguez to the Yankees, Alfonso Soriano and Joaquin Arias to the Rangers.

Soriano still continued to be a very successful player for several years, but only the next two were with the Rangers. In 11 seasons after the trade, Soriano slashed .266/.318/.499, with an .817 OPS. He was worth 18.8 bWAR in that span. In comparison, A-Rod slashed .283/.378/.523 with an OPS of .900. He was worth 54.0 bWAR in 12 seasons after the deal.

Joaquin Arias never panned out, spending most of his career in the minor leagues. After the trade, Arias played 701 games in the minors, and just 474 in the MLB. He was worth a total of -2.7 bWAR in his major league career.

In 2005, A-Rod led the AL in home runs (48), slugging percentage (.610), OPS (1.031), and OPS+ (173). In 2007, he again led the AL in all four categories, as well as posting a league-best 156 RBIs.

He was the offensive catalyst for the Yanks’ 2009 championship, batting .365 with 6 home runs and 18 RBIs in the ’09 postseason. To put it simply: the Yankees do not win their 27th World Series without A-Rod.

Trading for Luke Voit and Gio Urshela

These were separate trades, of course. But, squeezing them together allows me to add another move on the list, so just go with it.

In July 2018, Cashman sent Chasen Shreve and Giovanny Gallegos to the St. Louis Cardinals in exchange for Luke Voit and cash considerations. Voit had played just 70 major-league games prior to the deal. However, he instantly burst onto the scene in the Bronx that year, slashing .333/.405/1.095 with 14 home runs in just 33 games.

His 2018 sample was no fluke, either. Voit has a slashline of .279/.372/.543 and 57 home runs in 213 games as a Yankee. MLB Network recently named him the third-best 1B in baseball entering the 2021 season.

Gio Urshela was acquired from the Toronto Blue Jays in August of 2018, in exchange for cash considerations (boy, this “cash considerations” guy really gets around, doesn’t he?). Prior to the deal, Urshela had a career batting average of .225, and just 8 home runs in 167 games.

However, he quickly became another breakout acquisition. In 2019, Urshela hit .314, with an .889 OPS and 21 home runs in 132 games. In 2020, he was worth 2.1 bWAR in just 43 games, which translates to 7.9 across a full season. MLB Network recently ranked him the 9th-best third baseman in the MLB. Not bad for a guy that was traded for cash.

The Entire 2008 Offseason

This is also technically a series of moves, but I’m still counting it as one. The Yankees missed the playoffs in 2008, winning just 89 games. The following offseason, Cashman wasted no time improving the team.

First, in November, he sent Wilson Betemit, along with minor-leaguers Jeff Marquez and Jhonny Nunez, to the Chicago White Sox in exchange for Nick Swisher and prospect Kanekoa Texeira.

A month later, Cashman and the Yankees introduced a pair of star pitchers. He signed C.C. Sabathia to a 7-year, $161 million deal, and inked A.J. Burnett to a 5-year, $82.5 million contract. Less than two weeks later, the team also introduced switch-hitting first baseman Mark Teixeira.

The next year, bolstered by new additions, the Yankees won the AL East after going 103-59. Sabathia won an AL-best 19 games, with a 3.37 ERA. Teixeira led the AL in both home runs (39), and RBIs (122), while posting a .948 OPS. Swisher hit a career-high 29 home runs, with an .869 OPS. Burnett surpassed the 200-innings mark, posting a 4.04 ERA and a 114 ERA+.

They went on to conquer the postseason, beating the Phillies in 6 games to win their 27th World Series. In the playoffs, Sabathia specifically excelled, going 3-1 with a 1.98 ERA, and winning the ALCS MVP award.

While the Yankees already had offensive stars like Alex Rodriguez, Derek Jeter, and Robinson Cano, postseason pitching legend Andy Pettitte, and of course, Mariano Rivera, the free agency splurge in late 2008 was essentially what put the Yankees over the top, giving them one of the deepest teams in the league on both sides of the ball.

Aroldis Chapman Traded to Cubs for Gleyber Torres & More

This was an easy choice. In 2016, the Yankees were obviously not going to compete. The team finished 84-78, and finished 4th in the division. At the trade deadline, Cashman flipped hard-throwing closer Aroldis Chapman to the Chicago Cubs, in exchange for a 4-player package.

The package was highlighted by then-19 year old shortstop Gleyber Torres, who was the Cubs’ top prospect at the time. Obviously, Yankee fans know what happened next. Torres debuted in 2018, and has slashed .271/.340/.493 in 309 games, with 65 home runs. He was an all-star in both 2018 & 2019, and received MVP votes in the latter year. The young infielder is still just 24, and for the rest of the league, it’s a scary thought that he is likely not done improving.

Sweetening the deal even more was the fact that Chapman re-signed with the Yankees after the season ended. He rejoined the team for the 2017 season, and has posted a 2.65 ERA, with 94 saves in 107 opportunities, since returning to the Bronx.

Of course, it’s worth noting that this trade wasn’t a failure for the Cubs by any means. Chapman instantly took over as their closer, and he helped the team win the 2016 World Series, their first championship in 108 years. That’s a trade that the long-deprived Cubs fans would take any day.

The Legend of Cashman

Cashman is signed through 2022, so he has at least two more years as GM in the Bronx. However, he has already made a lasting impact on the franchise, and will leave a legacy for years to come.

Happy anniversary, ‘Cash Man’.