Brian Cashman’s career with the New York Yankees has been highlighted by numerous successful deals which have greatly improved the state of the organization. 

Since taking over as the Senior Vice President and General Manager of the New York Yankees in 1998, Brian Cashman has had his fair share of success. As a result of countless strategic moves, he has brought six pennants and four world championships to the Bronx over his 18-year tenure.

Many of his best tactical approaches have been taken place in the offseason, immediately bettering the team’s chances for the following season when fans expect it the least.

Whether it is a few days after the World Series concludes, the winter meetings, or even after pitchers and catchers have reported, Cashman knows how to swing a deal — usually benefitting his side in the long run.

Negotiating while putting all cards on the table is an area in which he truly thrives.

With that said, some of his offseason swaps have impacted the club far more than others. Elite Sports NY took the time to sort out the abundance of transactions.

Here are Brian Cashman’s top winter moves since taking the executive reigns of the most successful franchise in sports.

Too Early To Call

December 5, 2014 — NYY receives Didi Gregorius; AZ receives Robbie Ray, Domingo Leyba; DET receives Shane Greene

Sep 27, 2016; Bronx, NY, USA; New York Yankees shortstop Didi Gregorius (18) watches his solo home run during the sixth inning against the Boston Red Sox at Yankee Stadium. Mandatory Credit: Adam Hunger-USA TODAY Sports

If Didi Gregorius continues to perform at this clip, showing that he is more than worthy as Derek Jeter’s replacement, this deal may end up being the steal of Cashman’s career.

Coming off a career year in which he smashed 20 homers, drove in 70 runs, maintained a respectable .276 average, and played a gold glove-caliber shortstop, the 26-year-old is a fixture in New York’s more-than-promising rebuild.

Green, who was an exciting young arm with New York prior to being dealt, has pitched to a brutal 6.44 ERA in his two years with the Tigers.

December 8, 2015 — NYY receives Starlin Castro; CHC receives Adam Warren, Brendan Ryan

Sep 9, 2016; Bronx, NY, USA; New York Yankees second baseman Starlin Castro (14) hits a single during the first inning against the Tampa Bay Rays at Yankee Stadium. Mandatory Credit: Adam Hunger-USA TODAY Sports

Talk about a success. Not only did the Yankees receive an explosive bat and capable glove in one young, poised, and determined second baseman, perfectly fitting the rebuild, but they regained the one substantial piece they dealt.

Adam Warren was reacquired at 2016’s August 1 trade deadline and made a huge impact for New York down the stretch. This all occurred while Castro was slugging his way to his first career 20 home run season, including a torrent month of August where he hti .313 with eight dingers and 24 runs batted in.

Sure, the potential is there for Castro to fall off, but early results are indicative of this move eventually working its way among Cashman’s best.

December 9, 2015 — NYY receives Chad Green, Luis Cessa; DET receives Justin Wilson

Aug 27, 2016; Bronx, NY, USA; New York Yankees starting pitcher Chad Green (57) pitches against the Baltimore Orioles during the first inning at Yankee Stadium. Mandatory Credit: Andy Marlin-USA TODAY Sports

If it was possible to judge a deal based on one year, this one could be chalked up as a win. Green has turned himself into arguably the best young arm in the Yankees’ system, and his 2016 dominance in Scranton earned him eight starts in the bigs.

Cessa was showcased in a similar way, finishing the season as a mainstay on the big league staff. He figures to play a large role in 2017.

Wilson, on the other hand, completely disproved the intial outlook of the deal. Many thought Cashman made a mistake in dealing his seventh inning guy, and a potential bridge to a monstrous back-end. However, the 29-year-old’s 4.14 ERA in 66 appearances with Detroit showed that his 2015 prowess may have been a fluke.

The success level of this deal is purely dependent on how Cessa and Green continue to develop, but it is definitely off to the start Cashman envisioned.

5. December 8, 2009 — NYY receives Curtis Granderson; DET receives Phil Coke, Austin Jackson; AZ receives Ian Kennedy

Mar 22, 2015; Port St. Lucie, FL, USA; New York Mets right fielder Curtis Granderson (3) talks with New York Yankees manager Joe Girardi (28) before the game at Tradition Field. Mandatory Credit: Scott Rovak-USA TODAY Sports

Cashman did not win the Yanks a championship with this one, but he received loads of production. For an overhyped prospect, a decent lefty reliever, and a one-hit wonder, New York got a guy who — combined between 2011 and 2012 — blasted 84 homers and drive in 225 runs in a two-year span.

Granderson also scored 148 runs over the two years while playing a brilliant center field. His 2011 campaign earned him an all-star nod, a silver slugger, and a fourth-place finish in AL MVP voting.

After pitching to a 4.25 ERA through five years with Detroit, Coke has been all over the place, even working his way back to the Yankee organization.

Aside from a stellar 2012 campaign, Jackson has been extremely pedestrian in the bigs. To take it further, Kennedy has turned himself into a solid major league starter, but his 21-4, 2.88 ERA 2011 season is the only year that really stuck out.

Although Granderson no longer puts on the pinstripes, this deal was a victory for Cashman and company.

4. November 13, 2008 — NYY receives Nick Swisher; CHW receives Wilson Betemit, Jhonny Nunez, Jeff Marquez

The definition of low-risk, high-reward. Fortunately for Cashman, he got the high-reward aspect of that statement.

Buying extremely low on Swisher, who was coming off career lows in batting average (.219) and slugging (.410), the Yankees got an everyday right fielder for their 2009 championship team. Fittingly enough, he played a huge role.

Playing in 150 games, jacking 29 homers, and driving in 82 runs, all while providing an additional switch-hitting presence, the clubhouse catalyzer contributed to a 103-win regular season in a large way. He completely loosened the tight nature of a success-driven team as well, which helped them win their 40th pennant and their 27th title.

 RELATED: If Chapman Won't Budge, The Yankees Must Move On 

In the three seasons that followed, Swisher averaged 25 homers and 89 RBIs as the primary guy in right field. This earned him his payday in Cleveland prior to the 2013 campaign.

On the other side of the spectrum, Betemit played 20 games in 2009, Nunez pitched to a 9.53 ERA in 7 games that year (his only big league opportunity), and Marquez ended up pitching five innings in his big league career.

Let’s just say this one worked out.

3. February 6, 1998 — NYY receives Chuck Knoblauch; MIN receives Cristian Guzman, Eric Milton, Brian Buchanan, Danny Mota

In Cashman’s first significant deal at the helm, he helped the Yankees take that next step following a crushing 1997 season in which they failed to repeat as world champs.

Sure, Knoblauch was not his Twins self, stealing 62 bases (’97) and consistently hitting north of .300. But he was everything the Yankees needed at the moment, coming up with timely hits which helped New York execute a three-peat (1998-2000) and win four straight pennants from 1998-2001.

He played a huge part in the historic 114-win campaign in 1998, eventually resulting in a 125-50 mark and the franchise’s 24th championship.

To put the deal into perspective, Cashman acquired Knoblauch for one extremely solid major league player (Guzman) and a bag of baseballs (the others).

2. February 18, 1999 — NYY receives Roger Clemens; TOR receives David Wells, Homer Bush, Graeme Lloyd

Well, you have to give something to get something. But when you look at how everything panned out, Cashman essentially got a steal when he acquired one of the best pitchers of all-time.

Clemens anchored the Yankees’ starting staff when they turned a brutal month of September in a World Series title in 2000, topping their crosstown rivals — the New York Mets — in five games.

He would then go on to win the 2001 AL Cy Young award, winning 20 games against merely three losses.

For the tremendous impact he made, you can make the argument that his years in New York were some of the worst of his legendary career.

Most fans, though, will step back and consider what Cashman gave away, what he got in return, and what the team was able to accomplish as a result. In the process, he kept the powerful presence away from division rivals Boston and Toronto.

1. February 16, 2004 — NYY receives Alex Rodriguez; TEX receives Alfonso Soriano, Joaquin Arias

Aug 12, 2016; Bronx, NY, USA; New York Yankees designated hitter Alex Rodriguez (13) tips his cap in a farewell gesture to the fans after the game against the Tampa Bay Rays at Yankee Stadium. New York Yankees won 6-3. Mandatory Credit: Anthony Gruppuso-USA TODAY Sports

This one particularly hurt for the Red Sox, as the Yankees swooped in and stole an all-time legend from the grasp of their arch rivals. Without even looking at what Cashman had to part with, consider the fact that A-Rod is one of the five greatest players ever to play major league baseball.

Put steroid allegations, disagreements with the executive ranks (including Cashman), and antics aside. In 12 years as a Yankee, Rodriguez sported a .900 OPS, smacked 351 round-trippers, and collected 1096 RBIs.

Additionally, he was — and no one will dispute this — the reason the Yankees won it all in 2009.

Throughout his tenure with New York, Rodriguez collected milestones such as 600 home runs, 3,000 hits, and 2,000 RBIs. Furthermore, he won AL MVP awards in 2005 and 2007 thanks to absolutely monstrous campaigns.

When he was released this past season, likely putting an end to his playing days, he had 696 career homers to his name — placing him fourth on baseball’s all-time home run list.

What the Yankees had to deal does not nearly equate with what they gained. Pulling off the deal in the latest stage of the offseason, with spring training starting, power-hitting second baseman Alfonso Soriano made his way to Texas and into a new stage of his career. He would become one of the better power guys in the game, making the transition into the outfield and eventually back to New York 10 years later.

As for Arias, his career never turned into anything substantial.

Whether you like A-Rod or not, and many certainly do not, you cannot deny that Cashman won big with this deal.

 NEXT: Top 10 Managers In New York Yankees History