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The Winners by Kipling by Greene

by Cary Greene

August 5, 2022


Deadline related dust from the flurry of moves made by MLB teams both leading up to and at this year’s August 2nd trade curfew is still settling. With MLB expanding the playoffs this year, the possibilities this year’s Trade Deadline brought were quite interesting and I couldn’t wait to learn what Brian Cashman had up his sleeve this year.

There is no denying that Cashman had made some outstanding moves in the early part of the 2022 season. When the deadline approaches, Cashman certainly moves in mysterious ways sometimes and this year, he maneuvered the trade ocean in very sub rosa fashion at times, like a submarine running in stealth mode. It was anyone’s guess where he would pop up. At the time of this writing on the morning of August 3, I’ve had 12-hours to contemplate and assess Brian Cashman’s Deadline maneuvers and this year, the way he made the moves he orchestrated reminded me of a stanza from the poem The Winners by one of my favorite all-time great writers, Rudyard Kipling.

“What is the moral ? Who rides may read.

When the night is thick and the tracks are blind,

A friend at a pinch is a friend indeed;

But a fool to wait for the laggard behind

Down to Gehenna, or up to the Throne,

He travels the fastest who travels alone.”

I’m left wondering still this morning, what is the moral? Are Cashman’s moves going to bring a ticker-tape parade to Manhattan, after the Yankees end their current twelve-year World Series championship drought in resounding fashion? One thing is certain, this year Cashman ran silent and deep. His transponder was off. He popped up in this port and that bay, then for long stretches it seemed as if he had vanished, only to resurface again in the least likely of spots. “He travels the fastest who travels alone.” Kipling's words echo in my mind this morning. This year, Cashman was a rogue operative, his 24-years of experience at the helm of the Yankees guiding him as he adhered to a strategy only he truly knew. All the while, it felt as if Cashman’s periscope was up. He was silently watching the entire market. He had made hundreds of phone calls, having touched-base with rival GM’s numerous times on multitudes of players.

Rumors connected the Yankees, and most other big market contenders, to a number of star players which Yankee fans and media personalities debated the merits of trading for right up until the deadline struck. Many in the media thought Cashman and the Yankees were going all-in on Luis Castillo but I never fell for it, primarily because I follow the Yankees quite closely and this season clearly started out with the feel of Cashman taking a stop-gap approach, trading for players who were short-term fixes and signing Anthony Rizzo instead of a big name like Freddie Freeman. Cashman is clearly in the process of implementing a plan that revolves around promoting key prospects and operating responsibly.

No doubt many fans wanted Cashman to trade for Juan Soto or Shohei Ohtani (a player who spurned the Yankees when he signed with the Angels) or Bryan Reynolds and so-on, but it was clear to me back in June what Cashman’s strategy likely would be. He wasn’t parting with his top prospects. He clearly had a plan that he was going to stick to. Even if the media didn’t know, Cashman knew exactly where he was and what he was doing the whole time. “He travels the fastest who travels alone.”

This year, my belief in how things would work out was so explicit that I wrote this article about what might happen back on July 7th, "What Brian Cashman Will and Will Not Do at this Year's Deadline". In retrospect, I wasn’t far off Cashman’s mark. I thought Cashman would prioritize improving the bullpen and add not one, but two outfielders. Specifically, I thought Cashman would trade with the Royals for left fielder Andrew Benintendi and possibly center fielder Chris Taylor as well, then work out a deal with the Cubs for righty reliever David Robertson before adding either all-star lefty Joe Mantiply of the Diamondbacks or perhaps all-star righty David Bednars of the Pirates.

Did Brian Cashman do everything I thought he would? Actually, He did significantly more. I truly didn’t expect him to trade for a top shelf starter, yet somehow he pulled it off. He acquired “the bulldog” Frankie Montas himself, a true #2 starter, someone that Aaron Boone could slot in behind Gerrit Cole in a playoff series. I didn’t think Cashman would part with the trade chips that it would take to land a Frankie Montas, but Cashman went after his man and he got him. What I was able to decipher was what Brain Cashman would and wouldn’t do - that much I got right.

I thought Cashman’s deadline approach might be to balance the Yankees needs with his desire to keep certain prospects who have clearly been deemed as “part of the plan” going forward and as I expected, Cashman didn’t wind up trading any of the core prospects he’s quite clearly building around - referring specifically to Anthony Volpe, Jasson Dominguez, Everson Pereira, Austin Wells and Trey Sweeney. I also didn’t want to see Oswald Peraza, Ken Waldichuk or Hayden Wesneski traded either, but I knew that without making at least a few of these names available, Cashman would never be able to make the significant moves he needed to accomplish.

According to SNY’s Andy Martino, Cashman apparently dangled Oswald Peraza to the A’s as part of a Frankie Montas proposal, so it was clear that Cashman was very focused on improving the Yankees rotation - something I wasn’t in favor of doing because I believed the right play was using Clarke Schmidt and or JP Sears as starters over the second-half of the season, while potentially leaning on unproven but promising rookies Ken Waldichuk or even Hayden Wesneski to eat innings as necessary and provide rest for a rotation that was clearly in need of help.

Once Cashman made it known to A’s GM David Frost that he wanted Montas, Frost’s priorities needed to be met if he were parting with a player of Montas’s stature, he needed to receive back a package of pitching prospects capable of reinvigorating the A’s pitching pipeline, rather than using the valuable trade chip that Montas represented to grab a potential star shortstop prospect like Oswald Peraza. Frost came away from the deal with not one, not two, but three stud pitching prospects, two of whom are ready to start right now for the A’s. Frost got what he wanted as he wound up snaring J.P. Sears, Ken Waldichuk and Luis Medina, along with second base prospect Cooper Bowman.

Of the bunch, I’m actually highest on J.P. Sears but I think Ken Waldichuk has a chance to be a middle of the rotation major league starter as well. That said, Luis Medina’s control is still a massive issue and Bowman is a minor league infielder who was a very far-off prospect who may have never impacted the Yankees. I think this was a superb trade on Cashman’s part because front-line starters win championships and they don’t come cheap.

Cashman also thriftily acquired the position player he was targeting several days ago, when he oversaw the trade with the Royals for Andrew Benintendi. I loved this move and I’ve wanted to see him in pinstripes for two years now, ever since Andy Singer first mentioned it here on SSTN! Cashman faked a lack of interest to the media, citing the Canadian Covid related “Restricted” list as the reason why the Yankees were going to pass. I wasn’t buying this at all and was just relieved to hear that Cashman got a deal done at a fair price. Benintendi’s skill set is just what the Yankee offense needed and I think he’ll pair really nicely with DJ LeMahieu, once Boone finally figures out that Judge needs to bat behind them both in the lineup.

An obvious trade most Yankees fans expected was to see Joey Gallo being dealt and to learn that Cashman unloaded him to the Dodgers for their 15th ranked prospect, Clayton Beeter, who instantly becomes the Yankees 10th best prospect and who owns a 15.3% Strikeout-Rate at Double-A Tulsa this season, was relieving. Cashman got a worthwhile pitching prospect to dream on in return for a player who clearly wasn’t a fit on the Yankees going forward.

As of Tuesday morning, I reasoned that since Aaron Hicks had a resurgent July, with his walk-percentage soaring into the top 2-percent of MLB while also playing strong defense that now equates to 2 outs above average, per Stat Cast - why would Cashman trade for a center fielder when Aaron Boone has stated that he loves Aaron Judge as the team’s primary center fielder?

Hicks was/is a good 4th outfielder and having guys like him and Benintendi in the lineup will make the Yankees really balanced and top-to-bottom - but hold everything! Cashman did wind up trading for a center fielder as I thought he would all along. Granted, I thought Cashman would go for Chris Taylor all the way, but he wound up snaring Harrison Bader from the Cardinals for Jordan Montgomery. Bader is an elite defensive center fielder who’s already accumulated 1.5 fWAR this season. He’s an elite base runner (BsR of 4.6 per Fangraphs), he doesn’t have a problem hitting into double-plays and he doesn’t strike out a lot. Granted, Statcast isn't enamored with him offensively as his exit-velocity is in the bottom 1% of the league and his hard-hit% is in the bottom 4% of the league. Bader certainly isn’t going to be Joe DiMaggio. Bader’s sprint speed (29.2) is in the top 6% of the league and he’s rated as being 5-outs-above-average by Statcast. Bader is basically light-hitting, blazing fast centerfielder with below average arm strength.

Do I like this particular trade, Montgomery for Bader and a player to be named or cash? Not particularly, but not because I don’t think Bader will help the Yankees. It was an expensive trade for the Yankees as Cashman gave up the team’s number 5 starter, a lefty who was having a pretty solid season all things considered. Trading for Chris Taylor would have been vastly less expensive to accomplish. Offensively, both Taylor and Bader would be/are platoon players on the Yankees as neither hits left-handed pitching well enough, though both are right-handed batters - go figure.

Bader is a vastly better base runner and his speed is a game changer. He’s also a notch better defensively than Taylor, which is hard to believe because Taylor is pretty good. Taylor though is easily better with the bat and though he strikes out at a much higher clip than Bader does, he also walks more and hits for a significantly better average. I think Cashman could have brought in Taylor for a mid-tier prospect and still kept Jordan Montgomery around for the stretch run and into next season.

However, I do watch every single Yankees game and I’ve noticed something that advanced stats simply won’t reveal. Aaron Boone was clearly getting frustrated with Jordan Montgomery’s lack of focus recently. Two starts ago, against the Mets, in a game I covered for SSTN, Monty and Boone butted heads as Monty didn’t want to come out of the game. I think the Yankees simply decided they had seen enough of Montgomery, he simply wasn’t effective against stronger lineups and with the postseason gauntlet that awaits the Yankees, perhaps they just decided Monty wasn’t part of the plan - in which case, I understand why Cashman made this trade.

While I predicted that Cashman would avoid position players that would cost large prospect hauls to acquire, like Juan Soto, Bryan Reynolds, Cedrick Mullens and even Ian Happ, I also predicted that Cashman would ultimately steer clear of trading for a starter like Luis Castillo, who’s asking price contained the letters e, p, l, o and v.

What I didn’t see coming was how determined Cashman was to add a top-tier arm like Frankie Montas and that he’d accomplish this considering how stiff the competition was.

Considering I’m also an A’s fan, the trade for Montas blew my phone up as I had both friends who are Yankees fans and friends who are A’s fans machine-gunning me for hours immediately after the deal was announced by Baseball Trade Rumors, Darragh McDonald, who is one of my favorite baseball writers! This one was a shocker!

Acquiring Montas makes the Yankees a different team altogether. Imagine a playoffs rotation of Cole, Montas, Severino and Cortes? That’s huge! Lou Trivino also happens to be one of my favorite A’s relievers and what Yankee fans are getting here is a guy who has a proven power-arm (touches 101 mph at times) and who is a ground ball pitcher who usually keeps the ball in the park. It should be VERY interesting to see what Matt Blake can do with Trivino. Jose Trevino is also a vastly better catcher than the A’s Sean Murphy is, so both Montas and Trivino pitching to Trevino should yield positive results.

It seemed very obvious that Cashman would also look to reinforce the bullpen and I thought most of the trades made after the Benintendi deal would be for relievers who could be part of a Yankees World Series push! I thought for sure Cashman would trade for the Cubs David Robertson and I had identified Arizona’s All-Star lefty Joe Mantiply, the Phillies Seranthony Dominguez and possibly, if the Pirates would consider moving him, All-Star righty David Bednars all as potential fits for the Yankees. That said, the market was flooded with available relievers and neither Bendars nor Dominguez were available, so Cashman continued to run silent and deep until he surfaced unexpectedly in the windy-city.

Good players with many years of team control don’t often get traded at the mid-season deadline. I was quite frankly shocked that Cashman pulled off a trade with the Cubs for Scott Effross, who has 5 1/2 years of team control, per Sportac. While I knew Cashman would absolutely make an attempt to improve the bullpen, I never would have predicted him to go for a really good young reliever with tons of team control. Cashman paid a steep, but fair, price for Effros, giving up Triple-A lefty Hayden Wesneski. I love this trade. Wesneski is a promising talent but he’s been shelled recently in Scranton and meanwhile, Effros is filthy. He’s a righty who has reverse splits, though he’s decent against right-handed hitters, as he’s lethal against left-handed batters. If the Yankees are going to win a World Series, they’ll need an arm like Effros throughout the playoffs. His wOBA of .245, which is in the top 7% of the league, combined with his pinpoint command and solid strike out ability should play great in the Yankee bullpen. He’s just what the doctor ordered!

Meanwhile, Cashman didn’t stop there, He acquired , Lou Trivino who also has 2 1/2-years of club control, per Sportac. Trivino could be another Clay Holmes type, someone Matt Blake and the Yankees analytics department feels could have redeeming qualities.

I also predicted that Juan Soto wouldn’t fit what Brian Cashman was looking to do at this year’s deadline, mainly because of the prospect cost that would have been involved in landing Soto but also due to redundancy (how many corner outfielders does a team trying to win the World Series really need?) coupled with the Nationals not really digging the Yankee farm system. The two teams just didn’t match up for Soto.

Dovetailing into that notion, there were a number of other players that trade rumors were swirling around who I weeded out as not fitting with what Cashman was willing to give up and this list of players included the Pirates Bryan Reynolds, Cedric Mullins and Austin Hayes of the Orioles, and the Cubs Ian Happ.

When evaluating the moves Cashman made both leading up to and at this year’s Trade Deadline, there is little doubt that Cashman made the Yankees a better team. I like each and every move he made. Operating behind the scenes, Cashman was sublime. The Yankees have better bat-to-ball skills now, the lineup is more balanced and faster, it’s better on the basepaths too and defensively, the Yankees are improved. The Yankees rotation is better suited for a playoffs push and the bullpen is much better as well. There really isn’t anything not to like.



Aug 05, 2022

we can debate the wisdom of giving up all those pitching prospects

and might have to evaluate Cashman's moves on the basis of how well Montas pitches

Cary Greene
Cary Greene
Aug 06, 2022
Replying to

That makes it an even more amazing trade! Somehow with all the tables and statistics and charts I miss that Montas has an extra year of team control. Wow. That is super news to me. Lol

That should really help the Yankee rotation for next season, massively in fact.

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