NEW YORK — Derek Jeter played his final game at shortstop for the New York Yankees in 2014. Twelve seasons later, the club is still trying to settle the position.
Didi Gregorius held the job from 2015 through 2019. Gleyber Torres and Isiah Kiner-Falefa took turns there before the Yankees handed it to a homegrown prospect. Anthony Volpe arrived in 2023 and won a Gold Glove as a rookie, but the Yankees optioned him to Triple-A on Aug. 4 this season to make room for prospect George Lombard Jr.
Lombard, the 26th overall pick in 2023, homered in his big league debut at Yankee Stadium in a 2-0 win over the St. Louis Cardinals. He hit .235 with two home runs through early September.
Behind him sits shortstop Dax Kilby, the organization’s No. 1 prospect and No. 78 overall in MLB Pipeline’s rankings, who is playing in the Arizona Fall League.
Utility man Jose Caballero filled in as well, making 66 starts at shortstop on his way to becoming an AL Gold Glove finalist in the utility category.
The Yankees have options at the position. What they have not had since Jeter is a shortstop who is both a fixture in the lineup and a star in the field.
On Sunday night, Rawlings handed the AL Gold Glove at shortstop to Tampa Bay’s Taylor Walls, who became the first Rays infielder to win the award. One of the other shortstop finalists led every AL player with 24 outs above average, according to Baseball Savant.
That player started 140 games at shortstop, stole 45 bases and made his third straight All-Star team.
He also plays for a club that just finished last in its division.
And now one Yankees writer has laid out what it would take to bring him to the Bronx.
A blockbuster built around Lombard
Anthony Ranaudo, a former big league pitcher who writes for Yanks Go Yard, proposed that the Yankees pursue Kansas City Royals shortstop Bobby Witt Jr.
Ranaudo described it as a hypothetical exercise, not a report of talks between the clubs. His proposed package starts with Lombard and adds Volpe as an upside piece.
He also suggested a big league ready pitcher such as Will Warren, Clarke Schmidt, Elmer Rodriguez or Carlos Lagrange. Lower-level prospects Yostin Pena or Wilberson De Pena would round it out.
One sample version sends Lombard, Volpe, Warren and Pena to Kansas City for Witt.
Ranaudo on the price
Ranaudo acknowledged the cost would hit the Yankees’ farm system hard, starting with the player the organization has treated as close to untouchable.
“The package would have to start with Lombard, and it would probably sting, badly,” Ranaudo wrote.
He expects the Royals would push for even more, targeting the next shortstop in the Yankees pipeline.
“Kansas City would almost certainly demand Kilby, the system’s top prospect,” Ranaudo wrote.
Ranaudo explained the lower-level prospects as a long-term bet for a rebuilding club, rather than immediate help.
“Think of that last part as a venture capital play,” Ranaudo wrote.
Witt has spoken warmly of Aaron Judge, who would be his teammate in the Bronx. Responding to Judge calling him one of the best players in the game, Witt returned the praise.
“It’s an honor. How he works, who he is as an individual both on and off the field, is special,” Witt said.
The contract clock behind the pitch
Witt signed an 11-year, $288.7 million extension with the Royals in February 2024, the largest contract in franchise history. He can opt out after the 2030 season and in each of the next three years.
That timeline gives any team acquiring him four guaranteed seasons, 2027 through 2030, before his first opt-out. Judge is under contract with the Yankees through 2031.
The deal pays Witt $19 million in 2027 and climbs to $35 million a year starting in 2029. Its luxury tax value is about $26 million per season.
Witt’s 2026 line was .281/.359/.441 with 18 homers, 33 doubles and 54 RBIs in 143 games. His 45 steals topped the 41 by Yankees second baseman Jazz Chisholm Jr., who is headed for free agency.
He won Gold Gloves in 2024 and 2025 and the 2024 AL batting title.
Kansas City holds every card
The obstacles are significant for the Yankees. Witt has a full no-trade clause, so he would have to approve any deal, and he remains the face of the Royals franchise.
Kansas City finished 69-93, last in the AL Central, and missed the playoffs for a second straight year. General manager J.J. Picollo’s end-of-season comments focused on pitching, not his shortstop.
“We need to get back to where we’re a top-10 rotation like we were,” Picollo said.
For now, the Yankees’ shortstop plan for 2027 still runs through Lombard, Volpe and Kilby.
What do you think? Leave your comment below.
