On July 24th, 2016, The New York Yankees stood a pretty hefty 7.5 games behind the first place Baltimore Orioles. Despite a star-studded and expensive roster, that team had waffled about in mediocrity despite their cup of coffee in the postseason just a year before. Veterans like Brian McCann, Jacoby Ellsbury, and Mark Teixeira were showing their age, and the team had been mired in laughable mediocrity since 2013. Most of the informed fanbase by that fateful, steamy, overcast July day in New York were ready for a change.

The very next day, the Yankees traded Aroldis Chapman to the Cubs for a prospect package headlined by Gleyber Torres. Just a few days later, the team would trade Andrew Miller to Cleveland and Carlos Beltran to Texas for similarly impressive prospect hauls. The team had been locked in an endless cycle of propping up expensive rosters built around aging, injury-prone, and ineffective veteran players with no future in sight and this flurry of deadline maneuvering by the Yankees front office represented a major shift in its team-building strategy. Players like Aaron Judge, Luis Severino, and Gary Sanchez suggested that the Yankees might be able to echo the recipe for success the team had in the late-90s and early-00s where a young, homegrown and sustainable core would make up the nucleus of successful championship teams, and in one short week, Cashman acquired players in that deadline whom appear poised to be a part of that core.

Yet, we have to consider the storm that brewed during the first half of the 2016 season which allowed Cashman to strike so effectively at the 2016 deadline. The two best teams in baseball at the time, outside of the AL East were the Cleveland Indians and Chicago Cubs. Those two teams were then, arguably the most success-starved franchises in baseball. It had been nearly twenty years since the Indians had made it to the World Series, and The Cubs, notably cursed at the time had built what looked to be the next great dynasty in Baseball despite losing a dramatic NLCS to The New York Mets the previous season. Both teams had formidable lineups and five solid starters, but both also had a glaring need for elite bullpen help at the time. The middling 2016 Yankees had the best relief corps in the game and fanbase ready for a change. Brian Cashman convinced ownership to abandon ship during this perfect storm, and energized the franchise by adding exciting young talent in a year where the team was never expected to win anything more than third place in their division.

In 2017, the Yankees surprised most of the baseball community by contending strongly for most of the year and even making aggressive buyer moves during that season’s trade deadline. Thanks to the contributions of players acquired by Cashman with his new glut of prospect wealth, the Yankees made it to Game 7 of the ALCS. The team’s acquisition of Sonny Gray for a prospect package headlined by Dustin Fowler and Jorge Mateo was particularly striking, and emblematic of Cashman’s demonstrated ability to let MLB’s market come to him, rather than vice-versa. Gray’s short career had been characterized by unreliability. He had Cy Young caliber seasons in 2014 and 2015, but his 2016 and 2017 campaigns were marred by injury and ineffectiveness. Reading the market, the package Cashman sent in return for Gray made absolute sense. Fowler, Mateo and Kaprielian were all exciting prospects, but each of the three were incredibly risky in their own right. It was a risk-for-risk move on Cashman’s part, and it paid off for the Yankees in the short-term, as Gray put together a solid second half in the 2017 Regular Season, and had a stunning (yet fruitless) performance in the 2018 ALCS against the Houston Astros.

The Yankees made another aggressive and unexpected roster move in the 2017-2018 offseason by trading for Giancarlo Stanton. The Giancarlo Stanton trade was another result of Cashman reading the league perfectly and letting an amazing deal come to him, rather than paying the sticker price for assets that might have made more sense for the Yankees on paper. Stanton’s former team, the Miami Marlins had been recently purchased and the new ownership group made it abundantly clear that they were looking to tear the team down. It was long expected that whichever team landed Stanton would give up a King’s Ransom in young, controllable talent. It seemed all but inevitable that Stanton would go a team with a serious need for a slugging outfielder, but due to Stanton’s own leverage, no deals worked out for the Marlins and the team was left holding a bag that contained a vocally disgruntled Giancarlo Stanton and his record-breaking contract. Enter Brian Cashman. The Yankees GM entered the offseason with a strong need to bolster the pitching rotation along with a clear mandate from ownership to stay below MLB’s luxury tax threshold. The trade market for pitching never materialized the way Cashman wanted it to, and free agent starters like Yu Darvish and Jake Arietta were too expensive for ownership. When the opportunity to obtain Stanton appeared, Cashman saw it as the best opportunity to improve team, and found a way to make what has the potential to go down as one of the most lopsided trades in Major League History happen. One Starlin Castro and few good-not-great prospects later, and the Yankees had the 2017 National League MVP on their roster along with a bit of salary relief from the Marlins.

Now in 2018, with a young core hurdling the Yankees towards being the World Series favorites by some accounts, the team is undoubtedly in a win-now position and this has led fans, writers and rival clubs to assume that the Yankees will be aggressive buyers at the deadline. The Yankees have been oddly vocal about their desire to add frontline starting pitching. Thus far in the season, talent at the caliber the Yankees likely need to give them a real boost toward a championship doesn’t seem to exist, or at least not at a reasonable cost. The Economy of the pitching market has led many talking heads to suggest that the J.A. Happs and Cole Hamelses of the world might cost the Yankees a Clint Frazier or Justus Sheffield.

Over the past few days, rumors of the Yankees being interested in acquiring Manny Machado from the Orioles have gone from whispers and “what ifs” to almost a sure thing by some accounts in a matter of days. Yankees fans are confused for a number of reasons. Machado was undoubtedly destined, in many of our eyes, to ultimately become a Yankee, but that dream was one that we had collectively agreed to postpone until November or December. Secondly, where would Machado play on this Yankees roster? The Yankees infield outside of first base has been outstanding this year. Didi Gregorious is beloved by the fanbase and is among one of the most productive shortstops in the league. Miguel Andujar would arguably be an AL ROY favorite were it not for Gleyber Torres, who also happens to be a Yankee. Even if Machado departs from his baffling insistence on playing shortstop, unless he puts on a first baseman’s glove, there doesn’t seem to be a place for him given the state of things.

Regardless, Machado, the now four-time all-star is at the forefront of Yankees rumors, with the team apparently making a tangible and reportedly “solid” offer to the Orioles on July 11th. Despite the questionable roster fit, and Machado’s impending free agency, Machado to the Yankees makes more sense right now for New York than any other move that currently seems within the realm of possibility for the team. Machado will move the needle for the Yankees far more than any of the mid-rotation starters that Cashman might have the ability or the stomach to acquire. Furthermore, Machado in the Yankees lineup would neutralize the rival Red Sox greatest strength-lauded left-handed starting pitching. Boston currently has a 3.5 game lead over the Yankees, and the two teams will play each other ten (!) more times in the second half. Chris Sale looks slightly less intimidating when you’re trotting out Manny Machado ahead of, behind, or among Aaron Judge and Giancarlo Stanton.

Because of Cashman’s ability to read Major League Baseball’s economy when it comes to acquiring players, and his willingness to strengthen the team in esoteric, non-paradigmatic ways, a Machado trade kind of makes perfect sense for the Yankees. The Yankees have the best farm system in baseball, and competitors for Machado have leverage to fill needs in their infield due to the availability of other infield help available at lower costs. The market could be poised to, again, fall right in Cashman’s lap. Machado to the Yankees might be the best case scenario, but even if the team can’t make an unlikely deal with Baltimore for Machado, the writing on Brian Cashman’s wall tells us that whatever moves he makes over the next three weeks aren’t likely to be the ones we expect, or are the most comfortable with. In Cash, however, We Trust.

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