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.

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.