Yankees: Brian Cashman’s Top 5 free agent pitcher signings

Brian Cashman has made plenty of big-name free agent pitcher signings as general manager of the New York Yankees. Many have played big roles in the success of the organization and World Series championships.  He has had success in the international free agent pool for pitchers as well and that impact is still being felt today.

Five pitchers that have stuck out in pinstripes after signing with the New York Yankees are ranked below. Gerrit Cole would be at the top of the list based on his past performance, but since he has yet to take the mound for the Yankees in a regular-season game he is excluded from this list for now.

5. Aroldis Chapman

Cashman and the Yankees first acquired Aroldis Chapman from the Cincinnati Reds in December of 2015 for four prospects. Cashman then traded the All-Star closer seven months later to the Chicago Cubs for four prospects, including Gleyber Torres, in a move that helped the Cubs win the World Series.

Over the ensuing winter, Cashman signed the hard-throwing left-hander to a five-year, $86 million contract to return to the Bronx for a second stint. After struggling in 2017 with a career-low 22 saves and a 3.22 ERA, Chapman has been the closer that the Yankees were expecting the last two seasons when they won 100 games each season.

Chapman had 69 of his 273 career saves in 2018 and 2019 and lowered his ERA each season. Working a fastball that tops 100 MPH and mixing in a devastating slider, Chapman could be a bigger asset moving forward in what could a shortened MLB season in 2020. Certainly, he has been the best closer the Yanks have had post-Mariano Rivera.

4. Orlando Hernandez

One of Cashman’s first International signings happened in March of 1998 when he signed Cuban right-hander Orlando Hernandez. He quickly became a major contributor to one of the game’s strongest starting staffs in his first season, by going 12-4 with a 3.13 ERA in 21 starts in the first of three straight World Series titles.

In 1999, he went 17-9 with a 4.12 ERA in a career-high 214 innings pitched, while he stuck out 157. In the playoffs that year, he went 3-0 with wins over the Texas Rangers in the Division Series, the Boston Red Sox in the ALCS and the Atlanta Braves in the World Series.

His 2000 regular season was not as great as he finished a game below .500 at 12-13, but he went 3-1 in the postseason to help the Yankees win their third straight championship. He was a 9-3 career postseason pitcher for the Yanks with a 2.65 ERA in 19 appearances.

3. Masahiro Tanaka

In January of 2014, Cashman signed Masahiro Tanaka to a seven-year, $155 million contract and the Japanese star has been durable and reliable as a pitcher for the Yankees in his tenure. In his first six seasons, he is 75-43 with a 3.75 ERA in 163 career starts. He has won at least 11 games every season, with his high-mark being 14 in 2016.

A two-time All-Star in 2014 and 2019, Tanaka is 5-3 in four postseason trips for the Yankees with a 1.76 ERA. He has spent the majority of his time pitching for the Yankees with a slight tear in his UCL. He did undergo arthroscopic surgery to remove a bone spur following the ALCS last fall, but as usual, he is ready to go when and if the MLB season starts amid the COVID-19 pandemic. When push comes to shove, he pitches his best with the most pressure on the line.

2. Mike Mussina

After winning their third straight championship in 2000, Cashman deepened the Yankees staff by signing Mike Mussina away from the Baltimore Orioles with a six-year, $88.5 million contract. He was nothing short of sensational in his time for the Yankees.

He won 123 games in his time as a Yankee and finished with an ERA of 3.88. He was durable each year as he pitched at least 150 innings a season and pitched over 200 innings in four years. In his final season in 2008, he went 20-9 with a 3.37 ERA at 39 years old before retiring. He was well worth every dollar Cashman spent on him.

1. CC Sabathia

When Cashman landed the left-handed CC Sabathia right before Christmas in December of 2008, he also got one of the major contributors to the 2009 World Series championship team 10 months later.

Carsten Charles Sabathia went 19-8 in his first season for the Yankees, but he took his pitching to another level in the playoffs. He tossed a four-hitter, allowing one run in a Game 1 ALCS win over the Los Angeles Angels. On three days rest, he pitched eight more innings of five-hit, one-run ball in a Game 5 win. Both performances earned him ALCS MVP honors.

Just as big as he was one the mound for the Yankees, he was even a bigger presence in the clubhouse as a calming veteran presence. He was a three-time All-Star for the Yankees, but battled knee injuries on the backend of his career until he retired following the 2019 season.