Dave Dombrowski has built a reputation as one of baseball's sharpest executives, but even the best swing and miss sometimes. In Philadelphia, that miss is wearing a $72 million price tag.

The Phillies have shown signs of life since Don Mattingly took the interim reins, but the team still sits nine games behind the Atlanta Braves in the NL East, tied with the Miami Marlins for second place. For a franchise that expects to contend, second place is a bitter pill to swallow—and Dombrowski has been fielding plenty of uncomfortable questions about how they got here.

FanSided's Tim Boyle recently zeroed in on what he calls Dombrowski's worst free-agent signing: Taijuan Walker's four-year, $72 million contract. "There might not be a worse Phillies free agent signing under Dombrowski than Taijuan Walker," Boyle wrote. "Coming off a good year with the New York Mets, the Phillies gave him $18 million a year for four seasons. Was it better or worse than going three years at a higher rate? That's an argument no one will win because Walker was inexcusably average even at his best."

Walker, a 14-year veteran, was released by the Phillies in April and remains a free agent. His final numbers in Philadelphia tell the story: a 24-25 record with a 5.12 ERA, and a staggering 23 earned runs on 36 hits in just 22.2 innings before his release. He was shuffled to the bullpen for long stretches, a clear sign the experiment had failed.

"Sure, he won 15 games in 2022 with the aid of a potent offense," Boyle added. "Shoved into the bullpen for a large part of it, the Walker signing was a miss by Dombrowski that'll continue to haunt the ball club. His roster spot and the finances invested in him would have been far better spent elsewhere."

The Phillies are still on the hook for the remainder of Walker's salary—dead money that now sits as a glaring reminder on the payroll. For a team built to win now, every dollar counts. And this one, as Boyle put it, continues to haunt.