With 103 wins in 2019, the New York Yankees tied for the most games the team has won in a single season since 1998, yet failed to advance beyond the American League (AL) Championship Series. New York led all Major League Baseball (MLB) teams in runs (943) and finished second to the Minnesota Twins in home runs (306), but pitching was an area of relative weakness.

The Yankees pitching staff registered a combined 4.31 earned run average (ERA) in 2019, which ranked 14th out of 30 teams. Consequently, the team’s general manager Brian Cashman entered the off-season poised to sign a prized free-agent starting pitcher. He accomplished that in December by signing right-handed pitcher Gerrit Cole to a record-breaking contract. Below are four players the Yankees have signed through mid-December:

1. Gerrit Cole

One day after the Washington Nationals signed pitcher Stephen Strasburg to a record-breaking, $245 million contract, the Yankees made Cole the highest-paid pitcher in the MLB by awarding him a nine-year, $324 million contract. In addition to garnering the highest total salary for a pitcher in league history, Cole’s $36 million annual salary is the most earned by any player. Mike Trout, who went on to sign a 12-year, $426.5 million extension with the Los Angeles Angels before the 2019 season, held the record previously with an annual salary of $35.5 million. Cole’s deal carries a full no-trade provision, and he can opt out following the 2024 season.

A 29-year-old native of Newport Beach, California, Cole was originally drafted by the Yankees in the first round of the 2008 MLB Amateur Draft, but instead opted to attend the University of California, Los Angeles. Three years later, he was selected first overall by the Pittsburgh Pirates. He recorded admirable numbers in five seasons with the Pirates, but took his game to another level over the past two seasons with the Houston Astros.

Cole finished as runner-up for the AL Cy Young Award last season and led the AL in ERA (2.50) and strikeouts (326) to go along with a career-best 20 wins. Through 1,195 innings pitched across seven seasons, the three-time MLB All-Star owns a career win-loss record of 94-52 in addition to a 3.22 ERA and 1,336 strikeouts.

2. Adam Warren

Less than a week after signing Cole to a record-breaking deal, the Yankees made a move to shore up its bullpen depth by signing right-handed pitcher Adam Warren to a minor-league contract. Warren, who has had two earlier terms with the Yankees, will earn $800,000 if he makes the team out of spring training. The 32-year-old player spent last season with the San Diego Padres and posted a record of 4-1 in addition to a 5.34 ERA and 25 strikeouts through 28-and-two-third innings pitched.

The University of North Carolina alumnus was selected by the Yankees in the fourth round of the 2009 MLB Amateur Draft and made his big league debut with the club in 2012. He was dealt to the Chicago Cubs before the 2016 season as part of a package for second baseman Starlin Castro, but returned to New York later that season in a trade involving Aroldis Chapman. Warren was dealt to the Seattle Mariners in 2018 for international bonus money.

Warren has pitched 407 of his 492-and-one-third innings with the Yankees and been most effective with the AL East team. Through 226 relief appearances and 20 starts with New York, Warren owns a 20-20 record to go along with a 3.18 ERA and 361 strikeouts.

3. Brett Gardner

New York is bringing back another familiar face in 2020 as the team agreed to a one-year, $12 million contract with outfielder Brett Gardner on December 10. The contract includes a $10 million club option for the 2021 season. The 36-year-old player provides valuable depth in the outfield, especially with Aaron Hicks recovering from Tommy John surgery, and is coming off a season in which he registered career-best figures in home runs (28) and RBI (74).

Selected by the Yankees in the third round of the 2005 MLB Amateur Draft, Gardner has spent his entire 12-year career with the franchise. He has 124 home runs, 524 RBI, and a .260 career batting average through 1,499 regular season games. Gardner played in the All-Star Game in 2015 and earned a Gold Glove for his fielding capabilities the following season.

4. Thomas Milone

New York also bolstered its organizational depth in December by signing outfielder Thomas Milone to a minor league contract. The 24-year-old native of Monroe, Connecticut, was selected out of high school by the Tampa Bay Rays in the third round of the 2013 MLB Amateur Draft and has spent seven seasons with the organization. Milone has played 594 career regular season games across five levels of minor league ball and has a .245 batting average in addition to 17 home runs and 160 RBI. He also has 77 doubles and 40 triples. He is coming off a season in which he hit a career-best .281 split between the Montgomery Biscuits and the Charlotte Stone Crabs of the Southern League and Florida State League, respectively.