Analyzing the Yankees’ 2022 trade deadline


This story was excerpted from Bryan Hoch’s Yankees Beat newsletter. To read the full newsletter, click here. And subscribe to get it regularly in your inbox.

As he decompressed from a frenzied Trade Deadline, Yankees general manager Brian Cashman made sure to thank his staff from top to bottom for the blood, sweat and tears they’d put in for weeks, from their pro-scouting to front-office executives, analysts and medical teams.

They volleyed untold amounts of concepts and proposals in the weeks ahead of Tuesday’s 6 pm ET cutoff point for outside acquisitions, feverishly pursuing some options that were batted away at the line of scrimmage and turning up their noses at others like a toddler asked to take a bite of brussels sprouts.

“Everything we try to do is to improve it, no matter what time of year,” Cashman said. “We feel like we’ve added impact and it came at prices, but we were on the clock. We certainly pursued a lot of different avenues, and what we were able to pull down, we feel good about.”

Trade 1: OF Andrew Benintendi acquired from Royals for LHP TJ Sikkema, RHP Beck Way and RHP Chandler Champlain
Benintendi boarded a jet bound for New York City on July 27, expecting it to be his final time traveling with his Kansas City teammates. The All-Star was right, but at least he was headed to the right destination.

“Ultimately, he brings athleticism, contact and really good bat-to-ball skills,” Cashman said. “Whenever he’s available for us — hopefully it’s for the whole way or most of the way — I think we’re a better team with him than without him.”

Trade 2: RHP Scott Effross acquired from Cubs for RHP Hayden Wesneski
Effross’ name has circulated in the Yankees’ back rooms since April, as the sidearming right-hander was amid a stellar rookie season. The 28-year-old Effross provides depth in the wake of season-ending injuries to Chad Green and Michael King, and has five more years of club control. Wesneski was the Yanks’ No. 7 prospect, according to MLB Pipeline, and is now the No. 8 prospect for the Cubs.

“That was an important addition, as we really took some hits when we lost Green and King,” Cashman said. “Trying to find ways to backfill [the bullpen] and reinforce it was certainly an important part of our discussions. … Effross is a guy who’s young, we’ve been paying attention to what he’s doing. He’s funky from a different angle, pounds the strike zone, doesn’t walk guys and gets a lot of ground balls. That’s something anybody would want to gravitate to.”

Trade 3: RHP Frankie Montas and RHP Lou Trivino acquired from Athletics for LHP Ken Waldichuk, RHP Luis Medina, LHP JP Sears and 2B Cooper Bowman
Once right-hander Luis Castillo was off the board, traded by the Reds to the Mariners, the Yankees shifted their focus to Montas. The 29-year-old had a 3.18 ERA in 19 starts for the A’s and was widely viewed among the top available starting pitchers at this year’s deadline. According to MLB Pipeline, Waldichuk was the Yanks’ No. 5 prospect (No. 3 with the A’s), Medina was No. 10 (now No. 7), Sears was No. 20 (No. 19 in Oakland) and Bowman was No. 21 (now No. 29).

“I wouldn’t say it was a natural pivot [from Castillo to Montas], but we had a lot of simultaneous conversations going on about a lot of different options that existed,” Cashman said. “Certainly, there were very few higher-end options that were available than [Montas], so we were able to conclude our dialogue with the Oakland A’s. We’re excited about what he’s able to provide for us along with what we already had.”

Trade 4: RHP Clayton Beeter acquired for OF Joey Gallo
The Yankees recognized that they needed to find a change of scenery for Gallo, who hit just .159 with 25 homers and 46 RBIs in 140 games with New York after being acquired ahead of last year’s Trade Deadline. In exchange, they picked up Beeter, a curveball artist who had a 5.75 ERA in 18 games (16 starts) at Double-A Tulsa this year, but owned 15.33 strikeouts per nine innings at the time of the trade. He’s ranked as the Yankees’ No. 10 prospect by pipeline.

“It didn’t work out here, but I do appreciate that Joey never stopped trying, never stopped working, never stopped caring,” Cashman said. “I think our crew saw all that in the clubhouse. They were rooting for him hard to succeed. All you can ask for is an honest effort and maximum commitment, and we got that. We know the caliber of player he is, but in the window of time we had, we were unable to unlock that for whatever reason.”

Trade 5: OF Harrison Bader acquired for LHP Jordan Montgomery
This was a move that generated shock in the clubhouse, with a red-eyed Montgomery ushered out to make his final comments with the interlocking ‘NY’ across his chest. A Gold Glove-winning center fielder who grew up in Bronxville, NY, Bader drew interest even though he is currently wearing a walking boot due to plantar fasciitis in his right foot and may not be able to play until September.

“Harrison Bader is one of the elite center field defenders in the game,” Cashman said. “He provides a lot of lanes for our manager when he’s healthy. Certainly, we did a deep dive into his medicals and there’s a lot of optimism and belief that sometime in September we’ll be able to unpack that present and deploy him … whether it’s coming off the bench to steal a bag or as a starting option in the outfield. It’s hard to get your hands on someone of that caliber, and unfortunately it costs us one of our homegrown players in Jordan Montgomery.”

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