The Case for Pirates Being Aggressive This Offseason
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PITTSBURGH — The Pittsburgh Pirates improved in 2026 overall, but they still haven't gotten to where they want to be.
The Pirates clinched their first winning season since 2018, going 82-80 in 2026, but still fell short of making the postseason, something they are aiming for in 2027.
Pittsburgh has the second-longest postseason drought in MLB, last making it in 2015, with only the Los Angeles Angels having a longer drought (2015).
The Pirates are close to achieving that goal, and they should make a serious push this offseason for it.
Pirates Have Best Team Since Previous Postseason Run
The Pirates made the playoffs in three straight seasons, 2013-15, clinching the National League Wild Card each time and making the Division Series in 2013, losing to the St. Louis Cardinals in five games.
Pittsburgh had a strong starting rotation, great bullpen, and stars in their lineup like outfielders Starling Marte and Andrew McCutchen, and big-time performers like third baseman Pedro Alvarez, second baseman Neil Walker and catcher Russell Martin.
The Pirates are in a similar position this time around, with a promising starting rotation, an improved bullpen and a strong lineup.
Pittsburgh is close to having a complete roster ready to compete for the postseason on Opening Day.
Bringing back free agent second baseman Brandon Lowe, who hit 35 home runs and was strong defensively, while adding a right-handed power bat and high-leverage bullpen arms would make the Pirates that much better so they can get off to a hot start and separate themselves early on.
Youth Should Lead the Way
The Pirates are a young team, with the top players younger than 30 years old and many players just completing their third season or less.
Pittsburgh's rotation is full of youthful arms, led by Paul Skenes (24), Braxton Ashcraft (27), Jared Jones (25) and Bubba Chandler (24), with Mitch Keller (30) the oldest.
The Pirates also have a young lineup, with center fielder Oneil Cruz (28), first baseman Spencer Horwitz (28), catchers Henry Davis (27) and Rafael Flores Jr. (25), shortstop Konnor Griffin (20), right fielder Esmerlyn Valdez (22) and third baseman Nick Gonzales (27).
Outfielders Bryan Reynolds (31) and Jake Mangum (30), first baseman Ryan O'Hearn (33) and Lowe (32), if he returns, would be the oldest players in 2027.
The Pirates have players entering their prime or in it, and they must take advantage of it.
Pirates Have Minimal Costs Heading into 2027
Pittsburgh only has two free agents, Lowe and left-handed relief pitcher Gregory Soto, while the rest are arbitration-eligible or pre-arbitration, giving them team control over the vast majority of their roster.
The Pirates have two players in their second year of arbitration, right-handed relief pitcher Yohan Ramírez and Cruz, plus eight players heading into their first season of arbitration: pitchers Carmen Mlodzinski, Jones and Skenes, catchers Endy Rodríguez and Henry Davis, plus infielders in utility man Jared Triolo, Gonzales and Horwitz.
Pittsburgh spent $100 million on their roster in 2026 for the first time in a decade, back when they were last competing for the postseason.
The arbitration cases will increase the Pirates' payroll in 2027, but they should still be aggressive with free agents and on the trade market, building the best roster they can.
The Time to Compete is Now
Pittsburgh, being a small market team, means that they only have so long a window to be competitive for the postseason.
The Pirates are in their best position to do so since their last playoff run, and they only have a few years left with their best talent, unless they sign them to long contract extensions, which is unlikely without a salary cap.
A lockout may make the 2027 season precarious and other teams cautious with their spending, but the Pirates should go all in and show everyone: the fans, other front offices and prospective players, that they want to win next year.
The Pirates won't be perfect next year, but they can't afford to not try and go all in.
It's been far too long for fans in Pittsburgh to go without postseason baseball, and it's time to stop living in the past.
Spend money, make moves, go after the players you want and do everything you can to ensure a spot in the playoffs.
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Dominic writes for Pittsburgh Pirates On SI, Pittsburgh Panthers Pn SI and also, Pittsburgh Steelers On SI. A Pittsburgh native, Dominic grew up watching Pittsburgh Sports and wrote for The Pitt News as an undergraduate at the University of Pittsburgh, covering Pitt Athletics. He would write for Pittsburgh Sports Now after college and has years of experience covering sports across Pittsburgh.