Yankees’ Future May Be Hurt by Deadline Failures

With the trade deadline now in the rearview mirror, the New York Yankees appear to be in no man’s land. They sit in last place in the American League East and 5 1/2 games out of the final Wild Card spot. There’s no denying that this season has been tumultuous to this point. In truth, the Yankee’s deadline failings are due to years of poor roster strateFailing isolated events. They are staring at a roster in flux by failing to do so.

New York was built on a flimsy foundation, running back the same roster as they did last year. A roster full of injury-prone, unathletic right-handed hitters. It coincided with a front office seemingly refusing to ask themselves tough questions. 

Even if they didn’t buy at the deadline, selling off assets in the final year of their contracts would have been more prudent. It remains to be seen what the Yankees vision is moving forward.

Years of Poor Roster Strategy 

There are many more questions than answers concerning the Yankees roster strategy. They were the last of 30 teams to make a trade at the deadline, with the only addition being a middle reliever. Even their roster-building approach has been perplexing to date. For instance, Cashman’s previous trade deadline in 2022 was shambolic. He acquired five players at the cost of farm depth, and precisely one has seen the field this year. Lou Trivino and Scott Effross got hurt almost immediately.

Meanwhile, Frankie Montas still needs to begin throwing after he was traded a year ago. Andrew Benintendi signed with the Chicago White Sox. That left Harrison Bader as the only player to play this season, and he’s had multiple injuries this season. The only actual move they made this past offseason was signing Carlos Rodon, who had only an eye-raising 7.33 ERA.

It shows New York’s deadline failings are due to years of poor roster strategy.

A Poor Offensive Strategy

Sitting 29th in the league in batting average, 26th in on-base percentage, and 22nd in runs isn’t the “Yankee Way.” Also, stranding 15 runners in their previous defeat to the Houston Astros wasn’t much help. In a two-game span against the Baltimore Orioles and Tampa Bay Rays, they struck out a franchise record 30 times.

Hitting coach, Dillon Lawson was let go for Sean Casey. However, the problems are much deeper than one coach. As much as he appeared in over his head, he still answered a large team of analytics people that pressed for exit velo and uppercut swings. Not conducive to high-contact baseball.

None of these issues should be seen as a surprise. For one, they don’t have a recognized left fielder – inconceivable. Outside of Aaron Judge and the perennially injured Giancarlo Stanton, there must be more power in the lineup. It’s overly right-handed, leaving them susceptible to bullpen lanes. Apart from Anthony Rizzo on the injured list, he’s their only plus lefty bat. It’s an extraordinarily aging, unathletic, and injury-prone roster.

It’s, therefore, hardly a surprise that the offense has collapsed. The team batted a collective .170 in the playoffs last year and struck out 30% of their at-bats.

The Yankees Deadline Hurt Them

Arguably, the biggest indictment of Cashman is his inability to build around prime stars like Judge and Gerrit Cole. Judge had one of the greatest seasons in the game’s history last season. Yet, the Yankees collapsed through August and September and got ignominiously swept against the Astros in the ALCS. The Yankees have a generational player in Judge and failed to take advantage of his rookie contract and record-breaking year. Further raising questions now that he’s on a nine-year $360 million contract, whether they will build around him as promised.

Cole has been every bit the stopper the Yankees envisaged when spending over $300 million to land him. Especially this season, he’s having a Cy Young caliber year. Yet the Yankees are presently in last place. It speaks volumes about their inability to build a roster of late. It also speaks to a wasted opportunity. Not only have they yet to take advantage of two big seasons from their stars, the roster is declining. They are destroying the prime years of their two best players due to years of poor roster strategy.

Trade Decisions Can Be A Consequence 

Last season’s Josh Donaldson trade will likely go down as one of the worst moves in modern Yankee history. It’s undoubtedly the worst trade in Cashman’s career to date. It was bewildering at the time. Gio Urshela provided stellar defense at third and an ascending bat at a fraction of the cost of inheriting Donaldson’s remaining $50 million contract. It made little sense at the time.

Donaldson was hitting .147 this season with just 15 hits in 106 at-bats with a -0.1 WAR. Although, Isiah Kiner-Falefa has been a valuable utility man this season, primarily playing outfield due to their lack of depth. A position he was ill-suited for and had to be moved from. Cashman attempted to solve the lack of depth in the starting rotation by dealing with Frankie Montas at last year’s deadline. Montas was hurt at the time of the deal and has been injured since—that cost New York valuable pitching depth in their farm.

Cashman’s other inglorious deal was trading for Joey Gallo. It was a pure analytics move; they wanted a three-true outcomes hitter with an uppercut lefty swing. However, as hard as Gallo tried, he didn’t have the makeup for New York. It was clear he was better suited to a smaller market. Gallo hit an astonishingly bad .160 with 194 strikeouts. This deal also cost them Ezequiel Durán, who is having a stellar season for the Texas Rangers, batting .280 with 14 homers and traded OPS. Those numbers would make him one of the Yankees best hitters this year.

Ignoring Left Field

One of the most bizarre miscalculations was going into this season without an everyday left fielder. A problem position for several years now. Cashman has yet to address left fieNow that Anthony Volpe is in the majors, ld for some time. Joey Gallo didn’t work. They decided to go with a left field combo of IKF, and Oswaldo Cabrera, two infielders at a premium position this sea. Billy McKinney has at least provided adequate performances this season, but the career journeyman should never have been the answer at a premium power position. The position is excelling, having one of the worst-performing left fields in the majors.

It was believed that the Yankees were holding out to acquire a left-fielder at the trade deadline, but Cody Bellinger was taken off the market. Perhaps the Yankees were too slow on the trigger for such a valuable player, as the Chicago Cubs winning streak meant he was taken off the market. So too, Bryan Reynolds, whom the Pittsburgh Pirates extended before the start of the season. After Randal Grichuk was traded to the Los Angeles Angels at the deadline, there appeared to be little incentive from the front office to move for a left fielder. Once again, it feels like the Yankees misread the market; this position needed to be addressed in the offseason, as waiting until the trade deadline put them at the mercy of other teams.

Curious Use of Prospects

One of the clearest examples of the Yankees poor roster strategy comes with their use of prospects. Now that Anthony Volpe is in the majors, Oswald Peraza is their top-ranked prospect. Peraza is their best glove at shortstop, providing a terrific cameo last season. Batting over .300 with .800 OPS last season, but the Yankees have shown little interest in finding a spot for him in their flooded infield.

Esteban Florial was once their prized outfield prospect, given a cup of coffee in the majors and promptly sent down and designated for assignment. He recently passed through waivers, returned to the Yankees Scranton affiliate, and hit the cover off the ball. However, the Yankees have kept him there and off the 40-man roster. For a team in desperate need of a spark in the outfield, it remains perplexing they would prefer journeymen with limited to no upside over a young prospect. Perhaps Everson Pereira gets a look in September, as he’s shot through their minor leagues with his exciting bat.

It all speaks to a need for a more coherent vision and strategy. They are still determining whether to stick or twist with their young prospects. They must maximize their value in a trade or use them on the roster effectively. In terms of developing prospects, they need to do a better job with Volpe, believe in him, and progress him more than they have done with past prospects.

What’s The Yankees Vision Moving Forward?

New York’s strategy remains to determine whether they sneak into the playoffs. They presently have a roster in flux. One thing is sure; the roster needs a massive overhaul in the offseason. They need to get younger and more athletic urgently. While certainly adding some quality lefty bats.

Currently, Yankee’s figureheads seem more focused on repeating lines like ‘turning the corner’ than showing an urgency to bring about changes. One World Series since 2009 attests to this. The Astros beat the Yankees every time in the playoffs. Tampa Bay made short work of them in October. Baltimore has gone from one of the worst teams in baseball to the top of the AL East since that quote. A coherent vision and accepting where they have made mistakes would help the organization move forward.

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