Back in 2016 when he was running the Cubs, Theo Epstein explained giving up top infield prospect Gleyber Torres in a package for closer Aroldis Chapman by asking, “If not now, when?” The Yankees’ championship drought is 13 years, which even using the late George Steinbrenner’s math would not equate to the 108-year drought experienced by the Cubs. But with a team this special, the same justification for going all-in at the trade deadline applies.
Yankees general manager Brian Cashman understands the stakes. He knows he must seize the moment. His team is too good for him to be passive when the deadline represents his last chance to significantly alter his major-league roster.
“You’re always trying to improve your club regardless,” Cashman said. “It’s always, ‘If not now, then when?'”
Which isn’t to say Cashman should be reckless. Few of the players known to be available in a trade project as Chapman-type difference-makers. The current Yankees also bear a certain similarity to the 1998 club that, in Cashman’s first year as general manager, won 114 games and the World Series without adding a single player at the deadline.
Cashman tried that year for future Hall of Famer Randy Johnson, who ultimately went from the Mariners to the Astros for Freddy Garcia, Carlos Guillen and John Halama in one of the all-time great deadline blockbusters. The Yankees try pretty much every year, a notable exception occurring in 2017, when owner Hal Steinbrenner, wanting to stay under the luxury-tax threshold in 2018, balked at the $60 million-plus remaining on Justin Verlander’s contract — a decision that backfired when Verlander was the ALCS MVP against the Yankees that fall. But while a reasonable case can be made for these Yankees mostly standing pat, they need 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, matching the franchise’s fourth-best record at the 86-game mark. They play in an era when teams face almost daily injury concerns. And they compete in an expanded playoff format that requires even the best clubs to keep pushing in the regular season for seeding, then navigate a postseason that consists not of one or two rounds, but a minimum of three.
Teams today seek every last analytical edge, every last marginal advantage. So while the Yankees rank third in the majors in rotation ERA, they should still look to add a starter, knowing Jameson Taillon has a 6.81 ERA in his last seven outings, Nestor Cortes is near his career-high in innings and Luis Severino has not carried a full workload since 2018. While they expect Domingo Germán, Jonathan Loáisaga and Zack Britton to return from injuries, Germán as a reliever 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-oriented outfielder who might help extend rallies in the postseason.
Even in the best of times, Cashman exhibits a wry, sky-is-falling sense of humor. He was only half-joking over the weekend when he told the Fox broadcasters that the Yankees’ astonishing success this season is only setting them up for crushing disappointment if they fail to win the Series. He is still smarting from the Yankees’ curious 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 the wild-card game.
The deadline can be the trickiest of beasts. The Yankees’ biggest splash a year ago, a trade for Joey Gallo, turned out to be ill-conceived. An under-the-radar move, the acquisition of Clay Holmes, proved 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 hit only 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 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 that defeated them in the ALCS in both 2017 and 2019, although the first of those series was tainted by Houston’s illegal sign stealing. Against Astros pitching this season, the Yankees are batting .130 with a .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 only 4 1/2 games.
• The luxury tax should not be an issue.
The Yankees stayed under the threshold in 2021 just as they did in 2018, enabling them to reset their penalty rates to the lowest levels. Their current luxury-tax payroll, $262.2 million according to Fangraphs, would require them to pay a penalty of about $7.9 million. If they pushed their luxury-tax payroll to say, $275 million, the penalty would increase to about $13.5 million. Not an incidental amount. But also not oppressive for a high-revenue club. The Dodgers paid a $32.65 million luxury-tax bill last season.
• The players are doing their part.
It’s an unspoken doctrine of the deadline — when a team performs at a high level, the players expect the front office to honor their efforts by working equally hard to strengthen the roster. This won’t be a problem for the Yankees. Several team veterans, knowing of Cashman’s burning desire to end the team’s second-longest championship drought since its first of 27 titles in 1923, fully expect him to push for upgrades. Frankly, the only thing the clubhouse seems to be debating is which players the Yankees should get.
Which is where the conversations become difficult.
Going back to the 1998 deadline, Cashman had a team he described as “fantastic” with “really no weaknesses.” Johnson, although performing below his usual standards with the Mariners, was the big prize. “In theory, he would make everybody better. And you didn’t want your opponents to have him,” Cashman said. “But to be quite honest, the (Yankees’) chemistry was so amazing. And as good as he was, you didn’t know how he would mesh with our crew.”
Cashman had another concern about Johnson, as well. He noticed that when the Mariners came east, they frequently rearranged their rotation so Johnson would not pitch at the old Yankee Stadium. Cashman was grateful that the Yankee kept missing one of the best pitchers in the games, but found the pattern odd, so he asked Mariners manager Lou Piniella for an explanation. According to Cashman, Piniella replied, “He hates pitching in New York. He hates pitching in Yankee Stadium.
So, while the Yankees actually attempted to land Johnson, Cashman kept Piniella’s words in the back of his mind and chose not to meet the Mariners’ price. Nearly seven years later, Cashman went ahead and acquired Johnson, who by that point was 41. Johnson’s two years with the Yankees were uneventful, and included a memorable run-in with a TV cameraman when he went for his physical in Manhattan. Then and now, some players were not meant for certain markets.
Gallo, batting .163 with a .666 OPS in 468 plate appearances since joining the Yankees, turned out to be one such player. The Yankees value his baserunning and defense, at least when he is playing right field, but will likely part with him if they can find a taker. Cashman needs to be careful not to make a similar mistake, lest he screw up probably his best team since 1998.
How hard, then, should the Yankees push for the Reds’ Luis Castillo or the A’s Frankie Montas, knowing they would be coming from non-competitive teams in smaller markets? (Castillo had a good start against the Braves in the 2020 postseason and Montas also pitched in those playoffs, though not particularly well).
Would three additional years of club control with Pirates outfielder Bryan Reynolds actually be preferable to the Royals’ Andrew Benintendi as a two-month rental, considering the much higher acquisition cost and the uncertainty about how Reynolds might react moving from Pittsburgh to New York? No such doubt exists with Benintendi, who appeared in three postseasons with the Red Sox and was part of a Series champion in 2018.
Prospective trade partners covet the Yankees’ top two infield prospects, Anthony Volpe and Oswald Peraza, but Volpe almost certainly is a keeper, and perhaps the team’s starting shortstop in 2023. Cashman said the Yankees also have a “ton of pitching” in their farm system, which The Athletic‘s Keith Law ranked 22nd in February. Baseball America was higher on the Yankees’ system, rating it 13th.
Obviously, Cashman is not going to foolishly overpay, especially not 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’s going to try for whatever 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)