The Yankees’ 3 Biggest Trade Deadline Questions

With the deadline approaching, New York could pursue help for its rotation and outfield.

With the All-Star Game over and done with, the baseball world will turn its attention to the August 2 trade deadline.

The Yankees, with the best record in baseball and World Series hopes, figure to be buyers if they make any moves in the weeks ahead. However, there is one big leaguer they could move as they potentially pursue pitching and outfield help.

With the deadline right around the corner, here are three pressing questions facing the Yankees.

Will They Make a Significant Addition to the Rotation?

With a top-five ERA (3.20) and a top-10 fWAR (8.5), the Yankees have boasted one of baseball’s best rotations this season. However, a few factors could put a starter at the top of Brian Cashman’s wish list.

For one, Luis Severino just landed on the injured list, a frequent occurrence throughout his career. His low-grade lat strain is not considered serious right now, but Severino has already reached a workload (86 innings) that he has not come close to in recent years due to other injuries. Nestor Cortes, meanwhile, has thrown a career-high 95.2 big league innings.

If the Yankees want to make a huge rotation splash, Cincinnati’s Luis Castillo and Oakland’s Frankie Montas are two names to watch out for. Castillo recently stifled New York at Yankee Stadium. Otherwise, adding an arm that can eat up a few innings would also help New York.

Luis Castillo, Filthy 90mph Changeup...and K Spin/Lunge. 😷 pic.twitter.com/M6nFnKw4RU

— Rob Friedman (@PitchingNinja) July 14, 2022

Will the Yankees Trade Joey Gallo?

Gallo has been a disappointment in New York since being acquired before last year’s deadline. The 2022 season has been particularly tough for the outfielder, as he’s hitting just .164/.288/.342 with 11 homers, 23 RBI and a 38.1 K%.

Some believe a change of scenery could benefit Gallo. His agent, Scott Boras, recently hinted at that, telling the New York Post’s Joel Sherman and Jon Heyman, “I do know that there are a lot of teams that feel that Joey, in their market and their uniform, would be more of the normal than what he is in New York.”

While Gallo’s glove and on-base skills still provide value, the impending free agent and the Yankees may be better off parting ways.

READ: Joey Gallo 'Aware' of Possibility He Could Be Traded Before Deadline

Will the Yankees Add Another Outfielder?

Whether the Yankees move Gallo or not, they could search the market for another outfielder.

Aaron Hicks came on strong in July, hitting .333 with three homers and 11 RBI, but he’s been streaky and is prone to injuries. Combine that with Gallo’s struggles, and it’s easy to see why the Yankees have been linked to a handful of outfielders.

Potential options include Pittsburgh’s Bryan Reynolds, Chicago’s Ian Happ and Arizona’s David Peralta. Rumors previously connected New York to Kansas City’s Andrew Benintendi, but he seems like a long shot now. 

MORE:

• How Ex-Yankees From Last Year's Roster Performed in First Half
• Why This Cubs All-Star Is Ideal Fit For Yankees
• MLB Insider Reveals What Nationals Would Want From Yankees in Juan Soto Trade

Follow Gary Phillips on Twitter (@GaryHPhillips). Be sure to bookmark Inside The Pinstripes and check back daily for news, analysis and more.