How the Pirates Could Shock Everyone this Offseason

The only years the Pirates didn't have amongst the lowest payroll came in 2015 at $90,053,000 (24th), 2016 at $99,945,500 (20th) and $95,807,004 (24th) in 2017. 

Pittsburgh had a $86,464,000 payroll for Opening Day of the 2025 season, which was 26th in the MLB. It was also more than $20 million less than the next team in the National League Central Division, the Milwaukee Brewers, who had a payroll of $108,048,836, seventh lowest in the MLB.

The only teams with lower payrolls last season than the Pirates were the Miami Marlins at $68.9 million, Chicago White Sox at $74 million, the Athletics at $78.2 million and the Tampa Bay Rays at $82.9 million.

This lack of spending goes into free agency, as the Pirates haven't signed a free agent to a multi-year deal in over a decade

The last free agent to a multi-year deal since right-handed starting pitcher Iván Nova, who signed a three-year, $26 million deal on Dec. 27, 2016, and the last position player the Pirates signed to a multi-year deal was outfielder John Jaso for two years, $8 million on Dec. 23, 2015.

Why the Pirates Are Spending More This Time Around

Pittsburgh has had low payrolls and also poor performances over the past decade, which have resulted in no playoff appearances and seven straight losing seasons, the second-longest streaks in baseball, just behind the Los Angeles Angels.

The Pirates are also coming off a disappointing 2025 campaign that saw them finish 71-91 overall, last in the NL Central and with the fifth-worst record in baseball.

Despite this recent losing, the Pirates have a young corps and extra spending money that will give them the motivation and space needed for important signings.

NL Cy Young Award winner Paul Skenes leads a strong rotation, which also features veterans in Mitch Keller and Johan Oviedo, plus rookies in Braxton Ashcraft, Hunter Barco, Mike Burrows and Bubba Chandler.

The bullpen also provides strong arms in Justin Lawrence, Isaac Mattson, Carmen Mlodzinski and Dennis Santana, who helped the Pirates earn the most shutouts in baseball, 19, and the seventh lowest ERA (3.76)

This pitching staff gives the Pirates a chance at the postseason, but the money will go towards their hitting, which ranked amongst the worst of any MLB team.

Pittsburgh had the lowest slugging percentage (.350) and OPS (.655), the third lowest batting average (.231) and the eighth lowest on-base percentage (.305).

The Pirates also scored the least runs (583) and drove in the least RBIs (561), both lower than the 43-119 Colorado Rockies. They also hit the least home runs (117), 31 home runs less than then second-lowest team in the St. Louis Cardinals at 148 home runs, and had the seventh most strikeouts (1,422).

Cherington mentioning "flexibility" for working in free agency also comes from the Pirates moving players last season and getting their contracts off the payroll.

This includes trading third baseman Ke'Bryan Hayes to the Cincinnati Reds, which also moved the final $32 million over the next four seasons off their payroll from the eight-year, $70 million extension he signed in 2022.

Other moves included trading closer David Bednar to the New York Yankees and placing both infielder Isiah Kiner-Falefa and pitcher Andrew Heaney on waivers before the end of the season.

The Pirates will focus their efforts on finding hitters and everyday position players, especially for a left fielder and a third baseman, where they especially need starters next season.

Cherington also spoke on the failure of adding those key free agents over recent seasons, but that the talent on their pitching staff and having some space on the payroll will give them opportunities for adding those needed bats.

“We have tried,” Cherington said to Feinsand. “It's bound to happen; the odds increase a little bit each offseason with the combination of players seeing the strength of our pitching and the opportunity to win with that pitching foundation, and a little bit more flexibility. I think the combination of those two things give it a better chance, but we'll find out. The bottom line is we want to add to our position player group and we’ll explore all kinds of ways to do that.”