NLDS Pitching Matchup Features Two Former Pirates; Two Trades That Didn’t Pan Out
Not only does Wednesday’s National League Division Series game three feature two teams in the same division as the Pittsburgh Pirates, but the pitching matchup consists of two right-handers who used to wear the black and gold.
On the mound for the Milwaukee Brewers, who will go to the National League Championship Series for the first time since 2018 with a win, is Quinn Priester.
The Pirates selected Priester in the first round of the 2019 draft. He made 20 appearances/14 starts with the Pirates between 2023-24 and went 5-9 with a 6.46 ERA.
Priester was traded by the Pirates to the Boston Red Sox at last year’s trade deadline in exchange for infielder/outfielder Nick Yorke. Priester was dealt to the Brewers early in the 2025 season, and the 25-year-old played a big part in helping Milwaukee earn a division title.
Yorke played in 22 games with the Pirates this season at the end of the year and hit .232 with a .583 OPS, three doubles, one home run and eight RBI.
Priester totaled 29 appearances/24 starts with the Brewers this season and led baseball with an .813 winning percentage. He finished the regular season 13-3 with a 3.32 ERA. Priester set a Brewers franchise record by winning his 11th straight decision on Sep. 5 in a game — coincidently enough — against the Pirates in Pittsburgh.
Priester’s mound opponent will be Jameson Taillon, who will look to keep the Cubs’ hopes alive in a potential elimination games. Like Priester, Taillon was a first-round draft pick of the Pirates when they took him second overall in 2010 between Bryce Harper, who went first to the Washington Nationals and Manny Machado, who went third to the Baltimore Orioles.
Taillon spent four seasons in Pittsburgh from 2016-20 and went 29-24 with a 3.67 ERA across 82 starts. His best season came in 2018, when he went 14-10 with a 3.20 ERA in 32 starts and led baseball with a pair of complete games.
The Pirates traded Taillon to the New York Yankees in the 2020-21 offseason for a quarter of players — right-handers Roansy Contreras and Miguel Yajure, outfielder Canaan Smith-Njigba and infielder Maikol Escotto. None of the four players are still with the organization. It was part of the first wave of a rebuild that still has yet to come to fruition.
Contreras was considered a big piece of the Pirates’ future and looked the part early in his career. He went 5-5 with a 3.79 ERA in 21 appearances/18 starts in 2022. But his performance took a quick downturn and he was traded to the Los Angeles Angels for cash considerations in May 2024.
Yajure and Smith-Njigba played sparingly with the Pirates, and Escotto was released by the organization earlier this year after stalling out with Double-A Altoona.
Taillon, who is in the third year of four-year, $68 million contract he signed as a free agent with the Cubs, went 11-7 with a 3.68 in 23 starts in 2025.
To summarize, not only do the Pirates have to watch two teams from their division meet in the postseason — with one a lock for the NLCS — but they’ll be watching two of their own take the mound. And all they have left to show for the trades involving the two players is Yorke, who despite still being considered one of the organization’s top 30 prospects, barely got a chance with the Pirates this season despite the team’s abysmal offense.
That kind of tells you all you need to know, eh?
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