In 2016, while managing the Cubs, Theo Epstein explained that he had given up top infield prospect Gleyber Torres in a package for closer Aroldis Chapman by asking, “If not now, then when?” The championship drought the Yankees is 13 years, which even by the math of the late George Steinbrenner would not match the 108-year drought experienced by the Cubs. But with a team this special, the same justification applies to going all-in to the trade deadline.
Yankees general manager Brian Cashman understands what’s at stake. He knows he has to seize the moment. His team is too good for him to be passive when the deadline represents his final chance to make significant changes to his major league roster.
“You always try to improve your club anyway,” Cashman said. “It’s always like, ‘If not now, then when?'”
Which doesn’t mean Cashman should be ruthless. Few of the players known to be available in a commercial project as a Chapman-type difference maker. The current Yankees also bear some resemblance to the 1998 club, which won 114 games and the World Series in Cashman’s first year as general manager without adding a single player to record date.
Cashman tried his hand that year for future Hall of Famer Randy Johnson, who eventually switched from the Mariners to the Astros for Freddy Garcia, Carlos Guillen and John Halama in one of the greatest Deadline blockbusters of all time. The Yankees try almost every year, with a notable exception occurring in 2017 when owner Hal Steinbrenner, who wanted to stay under the luxury tax threshold in 2018, balked at the more than $60 million remaining on Justin Verlander’s contract — a decision that backfired kicked off when Verlander was the ALCS MVP against the Yankees that fall. But while a reasonable case can be made for these Yankees, who mostly stand still, they have to drop the hammer, even to the point of overkill.
Even after back-to-back losses to the Red Sox, the Yankees are 61-25, the franchise’s fourth-best tally in 86 games. You’re playing at a time when teams face injury concerns on an almost daily basis. And they compete in an extended playoff format that sees even the best clubs keep pushing seeding in the regular season and then have to navigate a postseason that’s not one or two rounds, but at least three.
Teams today seek every last analytical advantage, every last marginal advantage. Although the Yankees are third in the majors in rotational ERA, they should still try to add a starter, knowing that Jameson Taillon has a 6.81 ERA in his last seven games, while Nestor Cortes has an almost innings hit his career high and Luis Severino hasn’t carried a full workload since 2018. While Domingo Germán, Jonathan Loáisaga and Zack Britton will return from injuries, Germán as a backup or starter, manager Aaron Boone would still like another bullpen arm for added protection. And while the offense leads the majors in runs per game, the team would benefit from the addition of a contact-focused outfielder who could help extend postseason rallies.
Even at the best of times, Cashman exhibits a tongue-in-cheek, skyrocketing sense of humor. He was only half joking over the weekend when he told Fox broadcasters that the Yankees’ amazing success this season only sets them up for a crushing disappointment if they don’t win the series. He’s still suffering from the Yankees’ odd underperformance in 2021, calling it “one of my toughest years” as a GM, even though the team finished 92-70 before losing to the Red Sox in wildcard play.
The deadline can be the trickiest beast. The Yankees’ biggest hit a year ago, a trade for Joey Gallo, turned out to be ill-conceived. An inconspicuous move, the takeover of Clay Holmes, proved to be a masterstroke. But just as the Dodgers added Yu Darvish to a 104-win team in 2017 and Max Scherzer and Trea Turner to a 106-win club in 2021, Cashman needs to keep swinging. Yes, even if the market allows him to only hit singles, not home runs.
• This could be Aaron Judge’s last season with the Yankees.
Judge, who turned down a seven-year $213.5 million offer at the end of spring training, is four months away from becoming a free agent. And while most in the game expect him to stay with the Yankees, that could prove to be a dangerous assumption. Most expected Freddie Freeman to stay with the Braves.
• The Astros are a legitimate threat.
The Yankees are 2-3 against the Astros, the team they defeated in the ALCS in both 2017 and 2019, though the first of those series was spoiled by Houston’s illegal shield stealing. Against Astros pitching this season, the Yankees hit .130 with .520 OPS. Their lead over the Astros for the best overall record in the American League, essential for home field advantage in another potential ALCS rematch, is just 4 1/2 games.
• The luxury tax should not be an issue.
The Yankees stayed below the threshold in 2021, as they did in 2018, allowing them to reset their penalty rates to their lowest levels. Her current luxury tax payroll of $262.2 million, according to Fangraphs, would require a penalty of about $7.9 million. If they increased their luxury tax payroll to $275 million, the penalty would increase to about $13.5 million. No random amount. But not oppressive for a high-revenue club. The Dodgers paid a $32.65 million luxury tax bill last season.
• The players contribute.
It’s an unspoken doctrine of Deadline – when a team is playing at a high level, players expect the front office to reward their efforts by working equally hard to strengthen the roster. That won’t be a problem for the Yankees. Several team veterans, aware of Cashman’s burning desire to end the team’s second-longest championship drought since his first of 27 titles in 1923, expect him to push for upgrades. In all honesty, the only thing the clubhouse seems to be debating is which players the Yankees should get.
That’s where the conversations get difficult.
Looking back at the 1998 deadline, Cashman had a team he described as “amazing” with “really no weaknesses.” Johnson was the big prize, despite performing below his usual standards with the Mariners. “In theory, he would make anyone better. And you didn’t want your opponents to have it,” Cashman said. “But to be perfectly honest, the chemistry (of the Yankees) was so amazing. And as good as he was, you didn’t know how he would fit into our crew.”
Cashman had another concern for Johnson. He noted that when the Mariners came east, they frequently rearranged their rotation so that Johnson would not play at old Yankee Stadium. Cashman was grateful that the Yankees kept missing one of the best pitchers in games, but found the pattern odd and asked Mariners manager Lou Piniella for an explanation. According to Cashman, Piniella replied, “He hates pitching in New York. He hates pitching at Yankee Stadium.”
While the Yankees actually tried to land Johnson, Cashman kept Piniella’s words in mind and chose not to meet the Mariners’ prize. Nearly seven years later, Cashman moved on and took over from Johnson, who was 41 at the time. Johnson’s two years with the Yankees were mixed and included a memorable encounter with a television cameraman while he was in Manhattan on investigation. Then as now, some players were not destined for specific markets.
Gallo, who hit .163 with .666 OPS in 468 plate appearances since joining the Yankees, proved to be one such player. The Yankees appreciate his base running and defense, at least when he’s playing on the right field, but will likely part ways with him if they find a taker. Cashman must be careful not to make a similar mistake lest he screw up what is probably his best team since 1998.
Then how hard should the Yankees push for the Reds’ Luis Castillo or the A’s Frankie Montas knowing they’d be coming from uncompetitive teams in smaller markets? (Castillo got off to a good start in the 2020 postseason against the Braves, and Montas also played in those playoffs, albeit not particularly well).
Would three extra years of club control with Pirates outfielder Bryan Reynolds actually be preferable to a two-month lease from the Royals’ Andrew Benintendi, given the much higher initial cost and uncertainty of how Reynolds might react when moving from Pittsburgh to New York? There is no such doubt with Benintendi, who has appeared in three postseasons with the Red Sox and was part of a series champion in 2018.
Potential trading partners covet the Yankees’ top two infield prospects, Anthony Volpe and Oswald Peraza, but Volpe is almost certainly a goaltender and may be the team’s first shortstop of 2023. Cashman said the Yankees also have a “ton of pitching” on their farm system, which the athlete‘s Keith Law placed 22nd in February. Baseball America was higher in the Yankees’ system, finishing 13th.
Obviously, Cashman isn’t going to be foolishly overpaying, especially in a thin market. His description of the 1998 team – “fantastic…really no weaknesses” – is also a fairly accurate description of his current group. But if Cashman tried for Randy Johnson in 1998, he’ll be looking to snatch all the morsels he can grab and possibly more.
His team is that good. If not now then when?
(Top Photo: Justin Berl / Icon Sportswire via Getty Images)