![\"Ben](\"https:\/\/img.mlbstatic.com\/mlb-images\/image\/upload\/t_2x1\/t_w1536\/mlb\/zoo0xzvyhmxrr029lh25.jpg\")
<\/p>\nThe Pittsburgh Pirates are having one of their best seasons in ages. At the time of writing this, they are 53-50. They\u2019re well within the Wild Card hunt, and even a hot streak by them could slingshot them into division contention. The trade deadline is quickly approaching, and the Pirates look like buyers. However, the man at the helm of this season, General Manager Ben Cherington, is not the right man for the job.<\/p>\n
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The Pirates first hired Ben Cherington as Neal Huntington\u2019s successor in November 2019. Cherington came in at a rough time. The Pirates had a middle-of-the-pack farm system, had just come off a 93-loss season, and were dealing with a massive scandal involving former closer Felipe Vazquez\/Rivero. Cherington didn\u2019t get a fair shot in his first year either, as COVID-19 shut down much of the world, including baseball, leading to a 60-game season.<\/p>\n
However, the Pirates have found very little success in MLB since then. The Pirates have the sixth most losses in baseball since the start of the 2021 season. While they were rebuilding for the first handful of seasons, the recent results have not been pretty either. He has yet to win more than 76 games in a season since taking over as general manager.<\/p>\n
Many of the problems the Pirates are facing now are the same that have followed Cherington around for years. His first gig as a general manager was as the Boston Red Sox\u2019s GM. He took over after the 2011 season, a season in which the Sox won 90 games (albeit a season embroidered in controversy). The very next year, the Sox lost 93 games in Cherington\u2019s first year.<\/p>\n
2013 still stands as the lone season in Cherington\u2019s resume in which he oversaw a team that finished the year above .500. The 2013 Red Sox went on a tear, winning the World Series that very season. However, Cherington didn\u2019t do much of the heavy lifting. Per Baseball Reference WAR, just four of their top 12 players were Cherington-acquired players, including Shane Victorino, Mike Napoli, Koji Uehara, and Stephen Drew. Most of the Sox\u2019s core, including David Ortiz, Jon Lester, John Lackey, Dustin Pedroia, Jacoby Ellsbury, Clay Buchholz, and more, were all Theo\u2019s players.<\/p>\n
The Sox would go on to have below .500 seasons in 2014 and 2015 before being let go in August 2015. Cherington would join the Toronto Blue Jays\u2019 front office nearly a year later in September 2016 as a vice president of baseball operations. The Jays would finish each of 2017, 2018, and 2019 with at least 85 losses.<\/p>\n
When Ben Cherington goes \u2018all-in\u2019 to try and win, the results have not been very impressive, to say the least. 2026 is one of the only times he has had an \u2018all-in\u2019 type season<\/a>. The previous time he did this was in 2015. His big moves included signing Hanley Ramirez and Pablo Sandoval to lucrative contracts, and acquiring Wade Miley, Rick Porcello, and Justin Masterson. The Sox finished with just 78 wins. Ramirez and Sandoval were massive busts. Both Porcello and Miley had a sub-100 ERA+, while Masterson pitched just 59.1 innings with an ERA over 5.50.<\/p>\n One of the few things Cherington has proven he can do is build up a farm system. Baseball America ranked the Red Sox\u2019s system as a top five system<\/a> entering 2016, and had four prospects among the top 20 per BA\u2019s top 100 ranking<\/a>. Many of those players would help contribute to the Red Sox in 2018, when they won their last World Series, including Rafael Devers and Andrew Benintendi, with the likes of Yoan Moncada and Michael Kopech helping the Sox acquire their ace that year, Chris Sale.<\/p>\n Cherington also left the Toronto Blue Jays with one of the better farm systems in the sport. By 2021, the Jays had a top ten system, with many of their top prospects coming during Cherington\u2019s tenure as their VP POBO. Many of the Jays\u2019 players in the World Series last year were either players acquired while Cherington was part of their front office, or did most of their development while part of the Jays\u2019 organization.<\/p>\n Going into 2026, the Pirates had one of the best farm systems in baseball<\/a>. He has drafted very well for the Pirates, including taking Paul Skenes, Konnor Griffin, and Seth Hernandez three drafts in a row. His international signings are starting to pan out, as Esmerlyn Valdez is lighting up MLB pitching<\/a>; Wilber Dotel and Antonwe Kelly look like they could be long-term parts of the pitching staff. Edward Florentino is developing into one of baseball’s most interesting prospects. Even recent non-first round picks like Murf Gray, Khristian Curtis, and Easton Carmichael could be key members of a future Pirates squad.<\/p>\n However, that’s about where the positives end for Cherington. He’s able to build up plenty of young talent, but beyond that, he struggles to build around that. Most of his veteran acquisitions have fallen flat. Many of his trades have also not turned out well for his team. These are only the tip of his issues as well.<\/p>\n Cherington is in his sixth full season as the Pirates\u2019 general manager (seventh season overall), and the best he has to show for it is 76 wins. He has a chance to make the Pirates an extremely competitive ball club with the right moves at the deadline. However, if any of the last 14 years has shown us anything, it is that Cherington is not the right man for the job. With the constant missteps, poor acquisitions, and micromanaging of every team he oversees, Cherington is not the guy you want if you\u2019re trying to build a winning ball club.<\/p>\n Main Photo Credits: Charles LeClaire-Imagn Images<\/span><\/p>\n","protected":false},"excerpt":{"rendered":" The Pittsburgh Pirates are having one of their best seasons in ages. At the time of writing this, they are 53-50. They\u2019re well within the Wild Card hunt, and even a hot streak by them could slingshot them into division contention. The trade deadline is quickly approaching, and the Pirates look like buyers. However, the […]<\/p>\n","protected":false},"author":5765,"featured_media":126662,"comment_status":"open","ping_status":"closed","sticky":false,"template":"","format":"standard","meta":{"_lmt_disableupdate":"no","_lmt_disable":"","sfio_featured_image":false,"sfio_embed_code":"","_ef_editorial_meta_date_first-draft-date":"","_ef_editorial_meta_paragraph_assignment":"","_ef_editorial_meta_checkbox_needs-photo":"","_ef_editorial_meta_number_word-count":"","footnotes":""},"categories":[1071,26],"tags":[29265],"class_list":["post-126582","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-mlb","category-pirates","tag-esmerlyn-valdez"],"modified_by":"Evan Mazza, Site Editor","_links":{"self":[{"href":"https:\/\/lastwordonsports.com\/baseball\/wp-json\/wp\/v2\/posts\/126582","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/lastwordonsports.com\/baseball\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/lastwordonsports.com\/baseball\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/lastwordonsports.com\/baseball\/wp-json\/wp\/v2\/users\/5765"}],"replies":[{"embeddable":true,"href":"https:\/\/lastwordonsports.com\/baseball\/wp-json\/wp\/v2\/comments?post=126582"}],"version-history":[{"count":5,"href":"https:\/\/lastwordonsports.com\/baseball\/wp-json\/wp\/v2\/posts\/126582\/revisions"}],"predecessor-version":[{"id":126664,"href":"https:\/\/lastwordonsports.com\/baseball\/wp-json\/wp\/v2\/posts\/126582\/revisions\/126664"}],"wp:featuredmedia":[{"embeddable":true,"href":"https:\/\/lastwordonsports.com\/baseball\/wp-json\/wp\/v2\/media\/126662"}],"wp:attachment":[{"href":"https:\/\/lastwordonsports.com\/baseball\/wp-json\/wp\/v2\/media?parent=126582"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/lastwordonsports.com\/baseball\/wp-json\/wp\/v2\/categories?post=126582"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/lastwordonsports.com\/baseball\/wp-json\/wp\/v2\/tags?post=126582"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}A Rebuilding GM, Not A Winning GM<\/h3>\n
Where That Leaves Ben Cherington Now<\/h3>\n