Brian Cashman goes all in, acquiring Gallo and Rizzo to bolster the underachieving Yankees as the playoff race heats up

In 2016 Yankees general manager Brian Cashman executed what’s considered a masterful roster retooling at the end of July ahead of the trade deadline. That Yankees team was mediocre and aging, limping into the deadline just a few games above .500. Cashman decided to sell, believing the organization’s best path forward was through acquiring prospects instead of doubling down in the last two months of the season.

He flipped Aroldis Chapman to the Cubs and acquired Gleyber Torres. He sent Andrew Miller to Cleveland and received four prospects, one of whom was flipped two years later to acquire a starting pitcher. It was a unique deadline: Would there ever be teams more willing to part with top prospects than two teams desperate to break unfathomably long World Series droughts?

In the years since, Cashman has been notably quiet at the trade deadline. When weighing a baseball executive’s eternal dilemma — how much future value to give up in exchange for a shorter-term boost — often kept them from pulling the trigger on pitchers in particular when they needed them, Cashman’s philosophy was (and is) assiduously pragmatic: The Yankees were not going to overpay just for the sake of acquiring assistance.

It hurt the Yankees in the past. They let the likes of Justin Verlander and Gerrit Cole not only avoid pinstripes, but to end up in their rivals threads.

This year, with the Yankees once again being an average team with massive gaps between brilliant and awful, Cashman had to decide to go all in or let it play out.

“There’s no question that we’re in this,” Cashman said Friday. “So, it’s ‘What are we going to do about it?’ Are we going to sit back and just let it play out with what I think is an extremely talented roster as it is already? Or do we acknowledge that it’s not good enough, despite the talent, and it needs more? So the team got some fortification that we certainly hope will benefit.”

Cashman bought, acquiring left-handed batters Joey Gallo and Anthony Rizzo, along with starting pitcher Andrew Heaney and relievers Clay Holmes and Joely Rodríguez. They sent out 10 minor-league players and two major leaguers as part of this process. The Rangers will pay Gallo’s contract for the rest of the year, the Cubs will pay Rizzo’s, and there was cash coming back from the Angels with Heaney.

The Yankees will stay under the $210 million luxury tax threshold this year and made the process of acquiring players while playing payroll limbo look easier than it is. Cashman had a brilliant trade deadline and his praise needs to be as loud as the critics.

Rizzo, along with Gallo, will help balance out the Yankees’ overwhelmingly right-handed lineup. In 92 games with Chicago this season, Rizzo hit ​​.248/.346/.446 with 14 home runs. His underlying numbers are consistently strong: He makes good contact (81.8 percent, which would be top 20 in the AL), hits the ball hard, and his 15.7 percent strikeout rate is 23rd in MLB and about the same as DJ LeMahieu’s rate this season.

Rizzo could contrast well with the Yankees lineup, which got more swing-and-miss heavy with the addition of Gallo. But he’s also an excellent defensive first baseman and can upgrade the Yankees’ production and run prevention from the position.

Rizzo’s acquisition puts the team in an awkward spot with its first-base depth. The Yankees added Rizzo on Thursday and looked for a trade partner for Luke Voit, but when the deadline passed, Voit was still on New York’s roster. Voit has only appeared in 29 games for the Yankees in 2021 and is on the injured list for the third time this season, but manager Aaron Boone said Thursday that Voit may be able to come off the IL over the weekend. After the deadline, Voit’s timeline is now unclear.

With Voit still on the roster and not a clear line of playing time for him, the Yankees are going to have to get creative. Voit led the league in homers last year and has proven the ability to own the spotlight in New York so the bench isn’t a place for him.

The Yankees can own their name as the Bronx Bombers and slide Stanton into LF full time with either Judge or Gallo in CF. This moves Gardner to the bench, creating the most powerful 1-9 in MLB history?

Might not be what’s best, but it becomes really hard to avoid that temptation when filling out that lineup card each game.

Cashman’s approach was aggressive and restrained. It demonstrated that the Yankees see a path for themselves in the American League this year, despite their need to climb the standings to get there.

“Bottom line is, they all have to come together on a consistent basis in a short period of time to navigate the landscape of the final two months of this season and see if we can take an opportunity to be special,” Cashman said. “We’re right there. We’re recognizing and acknowledging that. Because of that, we’ve pushed more chips into the table to try to take care of our fans and take care of our team and take care of the opportunity that’s before us. Which is, you know, a chance to make the playoffs and take us to the title.”

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