PEORIA, Ariz. — Luis Castillo joins a growing subset of ace types who slipped away from the Yankees in trades, often to devastating results for the Yankees. 

In Brian Cashman’s 25 years as general manager, it was only the first time he shunned a No. 1 starter in the trade market did it perhaps still work out for the Yankees. Seattle’s Randy Johnson was available in July 1998. The Yankees were interested but pulled up short, as Cashman did not like the asking price and was concerned about Johnson’s personality in New York. 

Johnson was dealt to Houston instead and was brilliant, but the Yankees completed one of the greatest seasons ever and launched a threepeat, without Johnson, that was aided along the way by a trade for an ace — Roger Clemens. 

In a few other high-profile moments, though, failing to close trades arguably cost the Yankees titles. 

At the July 2010 deadline, the Yankees had an agreement in principle to obtain Cliff Lee from the Mariners for David Adams, Zach McAllister and Jesus Montero. Seattle said it had problems with Adams’ ankle in a physical review. The sides agreed to Adam Warren as a replacement. But then the Mariners wanted Eduardo Nuñez. The Yankees balked, believing it all was a ruse to get Texas to blink and include Justin Smoak in a package. The Rangers did. 

Lee pitched eight shutout innings and struck out 13 in Game 3 of the ALCS that year to give the Rangers the series lead for good in eliminating the defending champ Yankees. 

In 2017, the Yankees traded for Sonny Gray at the deadline. They were eyeing getting under the luxury tax in 2018 and didn’t want to trade for Justin Verlander and absorb the $56 million owed to him in 2018-19. Instead, the Astros traded three prospects who amounted to nothing and received $16 million from the Tigers for Verlander. In the ALCS, Verlander won both starts versus the Yankees, allowing one run in 16 innings. Verlander’s pitching had nothing to do with sign-stealing. Houston won in seven games. 

After that season, the Yankees were involved with Pittsburgh trying to obtain Gerrit Cole. Again Houston barged in, trading Joe Musgrove and three inconsequential players. Would the Yankees have won a World Series in 2018 or 2019 if they had completed a deal with Pittsburgh? 

Last trade deadline, Castillo was the starter the Yankees wanted. They offered a package fronted by outfield prospect Jasson Dominguez. The Mariners initially balked at including both well-regarded shortstop prospects Edwin Arroyo and Noelvi Marte, but, “We got to the point where the ‘now’ of our team [Seattle had MLB’s longest playoff drought, since 2001] is telling you it’s time,” said Mariners GM Justin Hollander on doing the four-prospect deal. 

The Yankees would not include Anthony Volpe. They never made an offer that had both Dominguez and Oswald Peraza in it. If they had, would they have gotten Castillo? 

Instead, the Yankees turned to Sonny Gray II — another apparent booby-prize from Oakland: Frankie Montas. 

Think about the cascade. If the Yankees had obtained Castillo, is there a reason to think he would not have signed the five-year, $108 million extension to stay in The Bronx (his preferred destination) that he signed with Seattle? (Multiple executives said it was understood in the game that Castillo was very open to an extension a year-plus before free agency.) 

If Castillo had been acquired and signed long term, would the Yankees have avoided signing Carlos Rodon, who now already is hurt? That would have left the payroll under the self-imposed, stay-under-the-top-tax-threshold of $293 million and might have allowed them also to retain Andrew Benintendi. 

More will have to play out to determine the fate of this — maybe Rodon or Montas will get healthy to help bring a Yankees title. Maybe Castillo will break down. Perhaps Dominguez or Peraza will become stars and not further versions of Nuñez. One constant this spring has been how much talent evaluators from other clubs like Peraza, Volpe and Oswaldo Cabrera and also see year over year improvement from Dominguez. 

Still, the Yankees’ history has been that when they have gone for aces — Clemens, David Cone, Mike Mussina, CC Sabathia, Masahiro Tanaka, Cole — they generally have been rewarded. And when they have gone for less, there have been a lot more Grays and Montases and Jeff Weavers and Javier Vazquezes, etcetera than there have been Hiroki Kurodas and Orlando Hernandezes. Is Rodon an ace or an injury-marred mirage? 

What makes Castillo so enticing, particularly to a club in a pressurized market such as the Yankees, is, in the words of Hollander: “When Luis is at his best is when the moments are the biggest.” Last July, with the baseball world knowing he was going to be traded, Castillo in three consecutive seven-inning starts, held the playoff-bound Braves, Rays and Yankees (in The Bronx) to one run apiece. 

At Yankee Stadium in his first Mariners start, Castillo allowed three runs in 6 ¹/₃ innings. Then, in his first home start in Seattle, the righty shut out the Yankees for eight innings while Cole was blanking the Mariners for seven. Castillo shut out the Blue Jays in Toronto over 7  ¹/₃ innings in the Mariners’ first playoff game in 21 years and held Houston to three runs in seven innings in the ALDS. 

“He brings high-end talent with a big-game mentality,” Hollander said. 

Castillo said: “It’s a different kind of adrenaline, and I like that.” 

After the 2020 season, Seattle’s baseball operations made a list of the players they thought would be available over the next 24 months and could most impact a jump from rebuilding to contention. Castillo was on the list. Seattle tried to obtain him during spring training in 2022. When the Reds made clear they would trade him at the deadline, Seattle accepted what Hollander called the “uncomfortable” aspect of giving up prospects they liked. 

“When you have a chance to capitalize on a prime-years, true top-of-the-rotation starter, who we believe is a top-10 starter in the league and who is trending even more positively than maybe his career track record indicated both in command and overall stuff, it was gonna be hard for us not to do that,” Hollander said. 

The Mariners did it. The Yankees didn’t. Is Castillo about to join the list with Lee, Verlander and Cole?