In 2016, while managing the Cubs, Theo Epstein explained that he ditched top inside prospect Gleyber Torres in a package for closer Aroldis Chapman asking, “If not now, when?” The Yankees’ championship drought is 13 years, which, even using the calculations of the late George Steinbrenner, wouldn’t equal the 108-year drought the Cubs had. But with such a special team, the same rationale for going all-in at the trade deadline applies.
Yankees general manager Brian Cashman understands the stakes. He knows he has to seize the moment. His team is too good for him to be passive when the deadline represents his last chance to significantly change his major league roster.
“You always try to improve your club despite everything,” Cashman said. “It’s always, ‘If not now, then when?'”
Which isn’t to say Cashman should be reckless. Few players known to be available in a commercial draft as Chapman-type difference makers. The current Yankees also bear some similarity to the 1998 club which, in Cashman’s first year as general manager, won 114 games and the World Series without adding a single player by the deadline.
Cashman tried out that year for future Hall of Famer Randy Johnson, who eventually moved from the Mariners to the Astros for Freddy Garcia, Carlos Guillen and John Halama in one of the all-time great blockbusters. The Yankees try almost every year, with 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 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 mostly standing Yankees, they have to drop the hammer, even to the point of exaggerating.
Even after back-to-back losses to the Red Sox, the Yankees are 61-25, tying the franchise’s fourth-best record at 86 games. They are playing at a time when teams are dealing with injury problems almost on a daily basis. And they’re competing in an expanded playoff format that forces even the top clubs to keep pushing in the regular season for the standings and then navigate a playoff that’s not one or two rounds, but a minimum of three. .
Today’s teams are looking for every analytical advantage, every marginal advantage. So while the Yankees rank third in majors in ERA rotation, they should still be looking to add a starter, knowing that Jameson Taillon has a 6.81 ERA in his last seven outings, Nestor Cortes is near his peak. in career 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 points per game, the team would benefit from the addition of a contact-oriented outfielder who could help extend playoff rallies.
Even at the best of times, Cashman exhibits a wry, giddy sense of humor. He was only half kidding this weekend when he told Fox broadcasters that the Yankees’ astonishing success this season only sets them up for crushing disappointment if they don’t win the series. He still suffers from the Yankees’ curious underperformance in 2021, calling it ‘one of my toughest years’ as general manager, even though the team finished 92-70 before losing to the Reds. Sox in the game of jokers.
The deadline can be the trickiest of beasts. The Yankees’ biggest crush a year ago, a trade for Joey Gallo, turned out to be ill-conceived. One 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 must keep swinging. Yes, even though the market only allows him to 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 players 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 that defeated them in the ALCS in 2017 and 2019, though the first of those series was marred by Houston’s illegal backboard theft. Against the Astros’ throw 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 just 4½ games.
• The luxury tax should not be a problem.
The Yankees stayed below the threshold in 2021 as they did in 2018, allowing them to reset their penalty rates to the lowest levels. Their current luxury tax payroll, $262.2 million according to Fangraphs, would result in them paying a penalty of about $7.9 million. If they pushed their luxury tax payroll to $275 million, the penalty would increase to about $13.5 million. Not an ancillary amount. But also not oppressive for a club with high incomes. The Dodgers paid a $32.65 million luxury tax bill last season.
• Players do their part.
It’s an unspoken doctrine of the deadline – when a team is playing at a high level, players expect the front office to honor their efforts by working just as hard to bolster the roster. It won’t be a problem for the Yankees. Several team veterans, knowing Cashman’s burning desire to end the team’s second-longest championship drought since its first of 27 titles in 1923, expect him to push for bets. at the level. Frankly, the only thing the clubhouse seems to be debating is which players the Yankees should have.
This is where conversations get tricky.
Going back to Deadline 1998, Cashman had a team he described as “fantastic” with “really no weaknesses”. Johnson, though performing below his usual standards with the Mariners, was the jackpot. “In theory, he would make everyone better. And you didn’t want your opponents to have it,” Cashman said. “But to be completely honest, the (Yankees’) chemistry was so amazing. And as good as he was, you had no idea how he would fit into our crew.
Cashman also had another concern about Johnson. He noticed that when the Mariners came east, they frequently rearranged their rotation so Johnson wouldn’t pitch at the old Yankee Stadium. Cashman was grateful the Yankee still lacks one of the best pitchers in the games, but found the pattern odd, so he demanded an explanation from Mariners manager Lou Piniella. According to Cashman, Piniella replied, “He hates pitching in New York. He hates pitching at Yankee Stadium.
So while the Yankees did attempt to land Johnson, Cashman kept Piniella’s words in mind and chose not to pay the Mariners’ price. Almost seven years later, Cashman went ahead and acquired Johnson, who was 41 at the time. Johnson’s two years with the Yankees were uneven and included a memorable encounter with a television cameraman when he went for his medical in Manhattan. Yesterday and today, some players were not intended for certain markets.
Gallo, batting .163 with a .666 OPS in 468 plate appearances since joining the Yankees, has proven to be one of those players. 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 can find a taker. Cashman must be careful not to make a similar mistake lest he likely screw up his best team since 1998.
So how hard should the Yankees push for Luis Castillo of the Reds or Frankie Montas of the A’s, knowing they’d come from uncompetitive teams in smaller markets? (Castillo got off to a good start against the Braves in the 2020 playoffs and Montas kicked off that playoff as well, but not particularly well).
Would three more years of club control with Pirates outfielder Bryan Reynolds actually be better than Royals’ Andrew Benintendi as a two-month hire, given the much higher cost of acquisition and uncertainty over Reynolds’ reaction to moving from Pittsburgh to New York? No such doubt exists with Benintendi, who appeared in three playoff series with the Red Sox and was part of a series champion in 2018.
Potential trade partners are eyeing the Yankees’ top two field prospects, Anthony Volpe and Oswald Peraza, but Volpe is almost certainly a goaltender, and possibly the team’s starting shortstop in 2023. Cashman said that the Yankees also had a “ton of pitches” on their farm. system, which Athleticism‘s Keith Law placed 22nd in February. Baseball America was higher on the Yankees system, ranking it 13th.
Clearly, Cashman is not going to stupidly overpay, especially not in a tight market. His description of the 1998 team – “fantastic…really no weaknesses” – is also a fairly accurate description of his current squad. But if Cashman tried for Randy Johnson in 1998, he’ll try everything he can catch, and maybe more.
His team is so good. If not now, then when?
(Top photo: Justin Berl/Icon Sportswire via Getty Images)
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