A rollercoaster of a 2026 season continued for Anthony Volpe on Monday night in Chicago.

With two on with two outs in the ninth inning and the Yankees leading the White Sox by five runs, Colson Montgomery popped up for what should have been the final out.

Volpe went to catch the routine fly ball in short right field, only to drop it and allow one run to score.

The Yankees ultimately won 9-5 with no further damage done, but not before they were forced to bring in closer David Bednar to replace Camilo Doval to wrap things up.

Bednar recorded the final out with ease to preserve the Yankees’ series-opening win.

Volpe had been having a strong game defensively, making two solid plays in the seventh inning with the Yankees up 5-4, including throwing out Montgomery at home off a relay throw from left field from Max Schuemann to preserve the lead.

The comical late error means that Volpe now has three more career errors than home runs since his debut in March 2023, with 56 errors and 53 home runs.

The latest addition to a growing list of blunders for the 25-year-old came amid chatter surrounding a potential promotion for top prospect and fellow shortstop George Lombard Jr.

Lombard, MLB.com’s N0. 20 overall prospect, has been highly productive in Triple-A Scranton Wilkes-Barre while Volpe and Jose Caballero have slumped with the major league club.

Caballero, who played third base Monday night, also made an error with one out in the ninth inning and that run ultimately scored.

Monday’s win to begin this four-game set marked Yankees’ first by more than three runs since July 9, when they bludgeoned the Rays 12-4.