Blockbuster Yankees Trade Rumor Targets $500 Million Pitching Ace For Rotation

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Manager Aaron Boone New York Yankees needs an upgrade to his starting rotation.

The New York Yankees are gaining momentum in their quest to win a second straight American League pennant, winning six of their last eight games to pull 3 1/2 games ahead of the second place Toronto Blue Jays in the AL East. But thanks in large part to a series of injuries, the Yankees’ starting rotation continues to look like the club’s Achilles heel.

The rotation as a whole has not been terrible, with a collective 3.73 ERA good enough for sixth in the AL. But much of that is the result of Max Fried, who so far has done everything to justify his eight-year, $218 million free agent contract.

Through nine starts, the 31-year-old lefty has won an AL-leading six with three no-decisions and an MLB-leading 1.11 ERA. After Fried, Carlos Rodon has posted a 3.29 ERA with no other starter under 4.61.

Top Baseball Insider Fuels Skenes Trade Speculation

But one trade rumor is gaining steam around baseball circles — a trade that would provide an instant boost to the Yankees rotation, raising it from merely adequate to elite. The rumor was given fuel when one of the most respected MLB insider journalists, ESPN’s Jeff Passan, suggested that the Pittsburgh Pirates could trade their 22-year-old, sophomore mound phenom Paul Skenes.

Jeff Passan says the Pirates’ best course of action might be to trade Paul Skenes and that teams will ask about him at the trade deadline this year.

We haven’t even had him for a full season yet.

In fact, Passan — appearing on The Pat McAffee Show Wednesday — appeared to advocate for the viewpoint that the Pirates should let Skenes pitch elsewhere, before saying that he believed Pittsburgh should hold on to their ace because, “with some of the players that they have coming up, they would have a chance to win if they were to go out and actually bring in some offensive players and sign some free agents.”

However, Passan also said that “there’s a real argument to be made that the best thing for the Pittsburgh Pirates would be to move Paul Skenes when he has his most value … It’s a depressing reality. I get it.”

Where would Skenes end up? As so often happens with big name players, the Bronx, New York, is at or near the top of the destination list. And indeed, Pinstripes Nation commentator Esteban Quiñones wrote on Thursday that the Yankees may be actively targeting Skenes.

“The New York Yankees’ perpetual hunt for elite pitching has found a new fixation: Paul Skenes,” Quiñones wrote. “As Pittsburgh’s organization spirals into another rebuilding cycle, whispers about the future of their generational talent grow louder, with Yankees supporters leading the speculation chorus.”

Also adding fuel to the trade rumors, the fact that Skenes himself, though only in his second year as a big leaguer, has gone public with his dissatisfaction over playing for a losing team.

“We’d better grow,” Skenes said of his team, following the firing of Pittsburgh manager Derek Shelton. “If we don’t grow, it’s a completely lost season.”

The High Cost of a Generational Pitching Phenom

If they did deal Skenes to the Yankees — admittedly a far-fetched possibilty, but as Passan implied, one that could be on the table — the Pirates would clearly demand a haul of prospects in return. Skenes was the No. 1 overall draft pick in 2023, National League Rookie of the Year and All-Star starter in 2024, and would have led MLB in ERA with his 1.93 mark if he had pitched 29 more innings.

For a generational talent like that, the Yankees would probably be expected to surrender at least two of their top three prospects, infielder George Lombard Jr., power-hitting outfielder Spencer Jones, and righty hurler Ben Hess.

Some Major League talent would likely need to be part of the deal as well — though the Pirates with their 27th-ranked payroll seem unlikely to take on any significant salary obligations.

And how much would it cost to pay Skene? Not much at first. The righty ace remains under team control for four more seasons, and is not even eligible for arbitration until 2027.

But when he finally hits the open market, according to Passan, look out.

“It would be no surprise to see Skenes — the best pitching prospect in a generation — parlay his productivity, age and marketability into becoming baseball’s first half-billion-dollar pitcher,” the ESPN insider wrote.

Jonathan Vankin JONATHAN VANKIN is an award-winning journalist and writer who now covers baseball and other sports for Heavy.com. He twice won New England Press Association awards for sports feature writing. Vankin is also the author of five nonfiction books on a variety of topics, as well as nine graphic novels including most recently “Last of the Gladiators” published by Dynamite Entertainment. More about Jonathan Vankin