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Looking back at Brian Cashman's 10 best offseason moves as Yankees general manager: Part 2

Detailing Cashman's five best moves at the helm of the Yankees

CC Sabathia speaks at Yankee Stadium during his introductory news conference in December 2008. (AP)

Brian Cashman is the longest-tenured general manager in baseball, and rightfully so. He has been the mastermind behind the Yankees' last four World Series titles and, more recently, helped spearhead the club's influx of homegrown talent.

Whether through free agency, trades, the draft or the international market, Cashman continues to keep the Yankees among the most competitive and talent-rich franchises in the sport. With the Yankees expected to make a splash or two this winter to bolster the roster for a championship run, let's take a trip down memory lane and look back at some of Cashman's best offseason moves while at the helm of the Yankees.

This is the second in a two-part series ranking Cashman's best moves. On Thursday, we featured the honorable mentions and Nos. 10-6 on the list.

5. Acquiring Roger Clemens from the Blue Jays (Feb. 18, 1999)

Cashman was able to trade for one of the best pitchers in baseball when he acquired Roger Clemens for David Wells, Homer Bush and Graeme Lloyd in February 1999. Wells was a fan-favorite but adding a five-time Cy Young winner was too good to pass up for Cashman. Clemens had two stints with the Yankees, helping guide them to World Series titles in 1999 and 2000 and added another Cy Young along the way. He went 83-42 over six seasons with the Yankees.

4. Acquiring Didi Gregorius from the D-backs (Dec. 5, 2014)

Cashman had his eyes on a young shortstop in Didi Gregorius for years and was finally able to swing a deal for him after Derek Jeter's final season. Not only has Gregorius exceeded expectations on the field, he's become a leader in the Yankees' clubhouse and a key part of the team's rise over the last couple yeras. After struggling in his first few months, Gregorius bounced back and is now batting .274/.319/.447 over four seasons with the Yankees. All Cashman had to give up for a quality starting shortstop was right-hander Shane Greene, who has been largely mediocre with the Tigers.

3. Acquiring Aroldis Chapman from the Reds (Dec. 28, 2015)

With Aroldis Chapman facing domestic violence charges, Cashman was able to trade for the four-time All Star for a package of low-level prospects in December 2015. He sent Caleb Cotham, Rookie Davis, Eric Jagielo and Tony Renda to the Reds in exchange for one of baseball's best relievers. The flamethrower showed his dominant form in 31 games with the Yankees before being sent to the Cubs in a trade-deadline deal. Cashman was able to buy low and sell high on Chapman as he acquired Gleyber Torres, Billy McKinney, Rashad Crawford and Adam Warren from Chicago. The Cubs won the World Series with Chapman, but the Yankees restocked their farm system and signed him back in the offseason, a big win-win for Cashman and the club.

2. Acquiring Alex Rodriguez from the Rangers (Feb. 15, 2004)

With the Rangers struggling financially due to Alex Rodriguez's massive contract, Cashman swooped in and traded for the seven-time All Star. Rodriguez was one of the best players in baseball at the time, and the Yankees found a way to accommodate him into their lineup. With Jeter at shortstop, the Yankees moved Rodriguez to third base and the two played together in the Bronx for a decade. While some doubt Rodriguez's success in New York, he did help deliver the franchise's 27th title in 2009, where he hit .365/.500/.808 with six home runs and 18 RBI in 15 postseason games. Despite some off-the-field controversies, Rodriguez batted .283/.378/.523 with 351 home runs and 1,096 RBI in 12 seasons in New York. He added two Most Valuable Player Awards and, in retirement, has become an advisor to the Yankees and resource for young talent coming through the team's system.

1. Acquiring Nick Swisher from the White Sox (Nov. 13, 2008); Signing Mark Teixeira (Jan. 6, 2019), CC Sabathia (Dec. 12, 2008) and AJ Burnett (Dec. 20, 2008)

While these are technically four separate deals, it's hard not to view Cashman's offseason ahead of the 2009 campaign as a single, unified plan to return the franchise to the top of the baseball world. The Yankees threw their weight around that winter, acquiring four players that helped propel the team to its 27th World Series title.

After missing the postseason for the first time in 14 years and with the new Yankee Stadium opening, Cashman knew he needed to make some big moves to keep the Steinbrenner family happy and to bring October baseball back to the Bronx. Cashman's first big move of the offseason was trading for Nick Swisher, who re-energized the clubhouse in New York, in exchange for Wilson Betemit and Minor League pitchers Jhonny Nunez and Jeffrey Marquez (New York also received Minor League hurler Kanekoa Texeira in the trade). Swisher slugged 29 home runs and 82 RBI after taking the right field job from an injured Xavier Nady and helped guide the Yankees to the World Series.

Cashman was also ready to spend in free agency and added $423.5 million to the payroll. First he signed first baseman Mark Teixeira to an eight-year, $180 million contract. Then he added pitchers CC Sabathia and AJ Burnett to seven-year, $161 million and five-year, $82.5 million deals, respectively. All three were vital to the 2009 World Series team, who won 103 games and the club's first title in nine seasons.

Teixeira had a nice career with the Yankees before retiring in 2016, while Burnett lasted three seasons before being traded to the Pirates. Sabathia, of course, is still with the Yankees after signing a one-year deal a couple weeks ago, and will look to win one more championship before retiring.