Deadline Outlook: How did the Yankees get Here and How can They Improve?

Charles Lippolis
6 min readMay 31, 2019

It had been more than 25 years since the Yankees were “sellers” at the trade deadline, but seeing the handwriting on the wall, the organization’s braintrust elected to sell off some of their prized players in the summer of 2016.

The success they’ve had since (both in light of, and in spite of) that summer has been written about countless times, but what brought me to that summer while pondering the prospectus for this one can be summarized in one word: decisiveness.

2019 presented a unique situation for the Bombers, being that they arrived at camp with seemingly no holes on their roster. In the past, it was common to hear speculation about the weakness in their starting rotation at the very least, but even that changed over the winter.

The club was sure to make a splash in their rotation before going to battle in 2019. Lo and behold, the exchange of top prospect Justus Sheffield for Mariners’ ace James Paxton appeared to be the perfect “win-now” move, and an opportunity to place a 1a they were searching for behind Luis Severino. Marrying that move to the retention of J.A. Happ and CC Sabathia set the Yankees rotation: Severino, Paxton, Tanaka, Happ Sabathia — a 5-man rotation more than capable of putting together another championship season.

In accordance with their 2017 and 2018 trade deadline moves, the Yankees also bolstered their already intimidating bullpen during the 2019 offseason. Retaining Zach Britton and adding Adam Ottavino put a combined four closers in the Yankees’ bullpen, an unprecedented reality in Major League Baseball that further cemented the club’s strength.

Last but not least, that Bronx Bomber lineup got a little tuneup. Coming off a season in which they set the record for team home runs, the team was optimistic about breaking it again in 2019 with health in the forecast for Aaron Judge, and a full season of Luke Voit. Didi Gregorius was expected to miss roughly half of the season recovering from Tommy John surgery, but combination of Gleyber Torres and proven veterans DJ LeMahieu and Troy Tulowitski was touted to be more than sufficient in his absence.

Fast forward to the end of May and the Yankees have a story you couldn’t have dreamt in March. Sitting atop the AL East and 15-games above .500, this Yankees club has built its identity around replacements Giovanni Urshela and Domingo Germán, and survived on standout performances from the likes of DJ LeMahieu and Clint Frazier.

It’s impossible to overstate what injuries have taken from this club, but we’ve reached a point where it can be said with confidence that the eye of the storm has passed. Paxton made his return to action this week, CC will be back for Sunday Night, Didi is prepared to meet the team in Toronto, and Giancarlo Stanton is looking to ramp up his rehab program once again. Dellin Betances and Luis Severino have both started to throw, and Aaron Judge has eased his way back into baseball activity. My point in short: the calvary is coming.

In this bizarro world the Yankees have been living in, they have yet to see their team at full strength, making it tough to asses what their team needs would be at every club’s final chance to improve during the season: the trade deadline. What they do know is that their organization’s depth has dazzled, giving them interesting leverage on the market. What they do with that leverage remains to be seen

“Trade for a starter” is a short-sighted, cry of desperation. However, that doesn’t mean it’s wrong, or that the Yankees couldn’t (or shouldn’t) improve their rotation. Clamoring for more starting pitching is different this season because it simply isn’t as easy for the Yankees to add a starter in 2019 as it was in 2017 and 2018, and it may not be necessary.

The first problem the Yankees face is the availability of a pitcher worth trading for. Of course, that has plenty of time to change, but by this time last season, J.A. Happ had already been widely identified as a man on the move, was a consensus improvement from the combination of Loaisiga, German, and Cessa that had been filling in for the Yankees. Speculation has followed pitchers such as Madison Bumgarner and Max Scherzer as their team’s have struggled, but nothing has been made formal regarding a top tier pitcher’s intention to leave, or a team’s intention to trade them. Alas, we’ll play the game.

After identifying a target, the Yankees would have to assess cost/benefit in the trade. Over the past three seasons, Brian Cashman has dominated transactions. Even in a moot trade such as the one for Sonny Gray, the Yankees were able to expense a minimal cost for what became an underwhelming benefit in Gray (and perhaps a net-negative). There can only be 25 (26 starting next season) men on the roster, and I think the Yankees have at least 28 big leaguers in their organization, so the slack to trade with is available at Cashman’s discretion. Who to move, though, is also a matter of what club(s) finds themselves as the seller in question. Filling the National’s team need is different from that of the Giants, Indians, or Blue Jays; making it challenging to pinpoint a package that works. Nevertheless, the Yankees would likely be looking at a situation where they’d be parting ways with a top prospect, a top young player, and a lottery ticket minor leaguer in order to get their foot in the door regarding a mid-summer Ace acquisition.

Finally, the Yankees would have to create space in their own rotation. As I referenced earlier, the rotation is essentially slotted when healthy: Severino, Paxton, Tanaka, Happ, Sabathia, and although Severino is still injured, he will likely be preparing for a return as these trade talks being to gain serious steam. CC’s knee will likely land him on the IL at least one more time this season, and with the way the Yankees have struggled to stay healthy, it would be naïve to suggest the Yankees won’t need to fill valuable starts down the stretch. Yet, the problem still presents itself — the Yankees already have five starters — six if you include Domingo German, and seven depending on where you stand with Jordan Montgomery.

The idea of adding another top starter to Severino, Paxton, Tanaka is exciting, but making it work is a problem in logistics that involves an equation more complicated than a simple addition.

In 2016, the Yankees took a firm stance on their vision for the organization’s future, and the value they had for their current players. In 2019, they will have to do the same.

The franchise is now at an impasse in which they are growing stale on “greatness” and craving “excellence”. Twenty-six consecutive winning seasons is a historic level of greatness, but a failure to reach the World Series over a decade span would ring through as a headline disappointment. With the roster and organizational depth the Yankees have built, tough decisions must be made at some point. The Yankees have done an unbelievable job at controlling the leverage both internally and externally, levying them the true authority during this decisive process to come — but a true commitment to excellence has to be matched with championship choices — choices that teams like the Cubs, Astros, and Red Sox have all found a way to make at the trade deadline.

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