When Cherington took the job in 2019, he set about replenishing the minor league system by dealing players who would have approached free agency by the time the Pirates were ready to compete. Now with the benefit of hindsight, we\u2019ll take a look at how these trades panned out in light of the recent departures.<\/p>\n Cherington\u2019s first move was to trade<\/a> star outfielder Starling Marte<\/a> to the Arizona Diamondbacks for shortstop Liover Peguero<\/a> and pitcher Brennan Malone<\/a>. Both were 19-year-old ranked prospects in Arizona\u2019s system at the time, Peguero at No. 18 and Malone at No. 9. It was thought that Peguero was the shortstop of the future. That never materialized, and he was recently placed on waivers<\/a>, as previously reported here.<\/p>\n The Pirates had high hopes for Malone as well. He was a first-round draft pick (33rd overall) of the Diamondbacks in 2019. Cherington told Sam Dykstra of MLB.com, \u201c[W]e’re excited about the ingredients he has that gives [sic] him the ability to be a starting pitcher.\u201d Alas, due to a plethora of injuries, Malone had trouble staying on the field. He never appeared in more than 10 games in the Pirates system until this past season, never advancing above Single-A. For his career as Pittsburgh property, he had a 4.50 ERA and 1.714 WHIP. Last season, he posted a 4.45 ERA and 1.694 WHIP in 25 relief appearances before being placed on the 60-day injured list on August 6. According to his transaction page, he was activated on November 6 and declared free agency the same day.<\/p>\n Marte was an All-Star and two-time Gold Glove recipient as a Pirate. It made sense to trade him because he was two years from free agency and reportedly unhappy in Pittsburgh. Pittsburgh was less than pleased with him, too, after his 80-game suspension for PED use<\/a> in 2017. Even so, now that Malone and Peguero are no longer with the Pirates, Cherington\u2019s first trade can be considered a disaster.<\/p>\n With Cherington\u2019s second major trade, All-Star first baseman Josh Bell<\/a> was traded<\/a> to the Washington Nationals for pitchers Wil Crowe<\/a> and Eddy Yean<\/a> after the 2020 season. Crowe was major-league ready and pitched for the Pirates from 2021-23, first as a starter, then as a workhorse reliever. The Pirates released him after the 2023 season, and he went off to Korea to resume his pro career. No matter. It was Yean, 20 at the time of the trade, who was thought to be the key to the deal.<\/p>\n However, Yean mostly struggled in the Pirates system. Starting and relieving, he was 25-19 with 20 saves, a 4.53 ERA, and a 1.513 WHIP. The 3.06 ERA he registered with Triple-A Indianapolis in 2025 is deceiving. That came with a 1.599 WHIP and 5.7 walks per nine innings. With the Pirates system so deep in pitching, Yean was unlikely to get more than a cursory look, if that, in 2026, so he also declared free agency on November 6. He\u2019s now back with Washington on a minor league deal.<\/p>\n The Washington Nationals signed Dominican right-hander Eddy Yean to a minor league contract, per sources.<\/p>\n Yean, 24, spent all of 2025 with Triple-A Indianapolis in the Pirates system, posting a 3.06 ERA over 70.2 innings.<\/p>\n Represented by The MAS+ Agency.<\/p>\n \u2014 Francys Romero (@francysromeroFR) November 15, 2025<\/a><\/p><\/blockquote>\n![\"With](\"https:\/\/lastwordonsports.com\/baseball\/wp-content\/uploads\/sites\/7\/2025\/02\/USATSI_22530259_168400885_lowres-300x200.jpg\")
Cherington\u2019s First Trade<\/strong><\/h3>\n
Eddy, We Hardly Knew Ye(an)<\/h3>\n
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