The New York Yankees kicked off their trade deadline with the acquisition of one former All-Star on Friday.

By trading for former Colorado Rockies third baseman Ryan McMahon, the Yankees filled the biggest hole in their lineup and added a left-handed bat with some pop to aim at the short porch in Yankee Stadium. Box No. 1, checked.

That leaves starting pitching and the bullpen as the two major agenda items left for the Yankees before Thursday’s deadline. How will they address those other needs, which are no less pressing?

MINNEAPOLIS, MN – JULY 13: Mitch Keller #23 of the Pittsburgh Pirates pitches against the Minnesota Twins on July 13, 2025 at Target Field in Minneapolis, Minnesota. (Photo by Brace Hemmelgarn/Minnesota Twins/Getty Images) MINNEAPOLIS, MN – JULY 13: Mitch Keller #23 of the Pittsburgh Pirates pitches against the Minnesota Twins on July 13, 2025 at Target Field in Minneapolis, Minnesota. (Photo by Brace Hemmelgarn/Minnesota Twins/Getty Images) Hemmelgarn/Getty Images

We haven’t heard much from the Pittsburgh Pirates yet at this deadline, but they’ve got a starter in Mitch Keller whose contract they’d like to get off the books, and a closer in David Bednar whose value is much higher now than it was a few months ago.

What might it take for the Yankees to land both? Here’s this writer’s best guess at a trade proposal that could work for both sides.

Yankees receive: SP Mitch Keller, RP David Bednar

Pirates receive: RHP Bryce Cunningham (Yankees’ No. 5 prospect), RHP Ben Hess (No. 7) C/1B Rafael Flores (No. 9), INF Roc Riggio (No. 11)

Rather than parting ways with one of the Yankees’ rising stars in Spencer Jones, George Lombard Jr., or Carlos Lagrange, this proposal applies a volume approach to give Pittsburgh some bats that should be ready to start next season, plus two cost-controlled replacements for Keller.

The 29-year-old Keller is owed just over $55 million from 2026 to 2028. He’s got a 3.53 ERA this year and ranks among the top 10 pitchers in the game in innings, alongside would-be teammates Max Fried and Carlos Rodón.

Meanwhile, Bednar has a 2.31 ERA and 12.3 strikeouts per nine innings this year despite a demotion to Triple-A in April, and he hasn’t given up an earned run since mid-May.

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