The Time For the Yankees to Make a Trade Is Now

The New York Yankees should begin to make trades before the MLB Trade Deadline, targeting outfielders and starting pitching as the team continues to struggle

In a season full of inconsistencies, the Yankees plunged to a new low over the weekend in Boston.

Gerrit Cole's worst start in a Yankees uniform, mixed with another disappearing act by the offense, resulted in a sixth straight loss to the Red Sox. New York hasn't started a season with this long of a winless stretch against their division rival in over a decade.

The weaknesses for this team are glaring. New York needs help in the outfield, scrambling to find production—especially in center field—since Aaron Hicks went down with a season-ending wrist injury. Brett Gardner has played 64 games (hitting .198) and Clint Frazier has been even worse at the plate, underperforming in his first chance at a full-time role. 

It's not just the offensive production from outfielders that's held this team back. The offense routinely struggles with runners in scoring position while grounding into the second-most double plays in all of baseball. For a club that lives and dies with the home run ball, rallies and stringing hits together are often a rarity.

New York could use a boost in the starting rotation as well. With Corey Kluber's shoulder injury keeping him sidelined for the foreseeable future, and Luis Severino's setback in his rehab from Tommy John delaying his highly-anticipated return, the starting staff hasn't been nearly as sharp as it was early on this season. 

So, as the Yankees dipped back to fourth place in the American League East on Sunday, with two weeks to go before the All-Star break, it's as clear as ever that something needs to change. 

General manager Brian Cashman spoke to the media over the weekend at Fenway Park, addressing his roster and the deficiencies that have presented themselves this season.

Cashman—who has already assured that this club will be buyers at the Trade Deadline—explained that while he and his staff haven't shied away from reaching out to other teams throughout the first half of this season, there simply isn't "any momentum" right now on the trade market.

“I don’t get a sense that there’s a feeling of action right now from the industry," Cashman told reporters. "That doesn’t mean that people can’t make a deal, or won’t make a deal, but it doesn’t feel like there’s a lot of heavy activity ready to burst.”

With this summer's MLB Draft moved back from its traditional date in June to mid-July, Cashman believes that teams are standing pat until they can transition their focus from draft-day prep to trade negotiations.

That's fair. Besides, the Yankees have some internal decisions to make regarding the financial implications of a trade (or two or three) regardless of the timing. Any major deal would likely take the club over the luxury tax, resulting in costly penalties for the organization. 

Forget the financials for just one second, though. Can the Yankees afford to wait until the Deadline (on July 30) to make a move? As much as this roster has the potential to be a World Series contender on paper—and it's still technically early in the season—it feels like this team is in danger of falling out of contention if these same trends continue.

New York enters a four-game series against the Los Angeles Angels on Monday sitting 6.5 games out of first place in their division and 5.5 games out of a Wild Card spot. Those aren't insurmountable deficits by any means, but with a 17-24 record against divisional opponents—5-14 against the Red Sox and Rays—it's going to take an emphatic reversal in the second half of the season against the franchises they play the most for the Yankees to assure a postseason spot.

Would managing general partner Hal Steinbrenner be willing to see his club narrowly sneak into the Wild Card round—or even miss the playoffs entirely for the first time since 2016—in order to stay under the $210 million Competitive Balance Tax?

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Cashman told reporters over the weekend that he and assistant general manager Michael Fishman had corresponded at one point or another with every other big-league club about a possible trade. 

That means the door for negotiations is already ajar with every other team. Besides, we've already seen other clubs make deals involving key contributors this season—like when the Rays shipped starting shortstop Willy Adames to the Brewers in order to make space for their top prospects at the big-league level. 

Manager Aaron Boone and his players have remained optimistic throughout the lows of this season, maintaining unwavering positivity regarding the abilities of this big-league roster. In the grand scheme of things, it's hard not to bank on track records. We're talking about a team that has championship caliber talent on both sides of the ball, a core that was two wins away from an American League pennant just two years ago. 

The small-sample size argument can't be used anymore, though. It's possible that the those in pinstripes just aren't going to produce to their potential between the lines this season. 

If that's the case, the time is now to make a move. Go out and acquire an outfielder to spice up the starting lineup, allowing Aaron Judge to remain in right field rather than relying on him routinely in center. Reel in a left-handed bat to finally provide some balance to a righty-heavy order. Add another hurler to flank Cole atop the rotation and keep this offense in ballgames.

It will take prospects, yes. Money will be a factor as well. But that's the case every year at the Deadline. You can argue that New York covets help this summer more than it's needed since Boone has been at the helm in the Bronx. 

Understanding that “trying to make trades is always difficult," as Cashman put it this weekend, time is of the essence. Even if other teams are being patient, it would behoove the Yankees to start making offers that those other clubs can't refuse. 

Otherwise, with the Trade Deadline over a month away, it could be too late. 

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Max Goodman
MAX GOODMAN

Max Goodman covers the New York Yankees for Sports Illustrated and FanNation. Goodman has been on the Yankees beat for three seasons. He is also the publisher of Sports Illustrated and FanNation's Jets site, Jets Country. Before starting Inside The Pinstripes, Goodman attended Northwestern University and the Medill School of Journalism. He earned his Bachelor’s Degree in Broadcast Journalism and Master’s Degree in Sports Media, graduating in 2019. At school, Goodman was an anchor and reporter with NNN SportsNight and played on the club baseball team. While at Northwestern, Goodman interned with MLB.com as an associate reporter covering the Miami Marlins. He also interned with ESPN, working as an associate reporter on Mike Greenberg's Get Up. Goodman is from New York City. He grew up in Hell's Kitchen. Follow Goodman on Twitter @MaxTGoodman. You can connect with him via email by reaching out at maxgoodmansports@gmail.com.