Insider Slams Pirates for Essentially Faking Free Agency

The Pirates also reportedly offered first baseman Josh Naylor a deal at around $78 million, before he re-signed with the Seattle Mariners on a five-year, $92 million deal.

Insider Criticizes Pirates' Free Agent Strategy

Jim Bowden of The Athletic wrote about his takeaways from the Winter Meetings and what he learned from the busiest time of the offseason.

Bowden looked at the Pirates and deemed them, "not serious spenders" and that their offers to Naylor and Schwarber were "simply eye wash."

He thinks that both Naylor and Schwarber were never going to sign those deals and that the Pirates need to overpay for that type of talent to even consider joining on, especially with their lack of recent success.

"There were a lot of people celebrating the Pirates for making offers for free agents Schwarber and Josh Naylor," Bowden wrote. "However, once the news got out that they offered Schwarber four years, $125 million and Naylor five years, $80 million, it became clear that the offers were more about being able to say they were willing to spend that money than they were a sincere attempt to get the player. They knew even if they offered the exact same money each player eventually got, or even $5 million to $10 million more for each player, they weren’t going to get either one.

"If a non-contending team like the Pirates wants to sign stars like Schwarber and Naylor away from their playoff teams, they have to grossly overpay or they’ll never get them. It’s what the Nationals did with Jayson Werth and the Tigers with Magglio Ordonez and Pudge Rodriguez.

"My point is this: The Pirates’ offer for Schwarber should have been six years, $180 million to $200 million; and for Naylor, six years, $120 million. Even then, it’s unlikely the players would have signed, but at least it would have given the players and their families something to think about. Once the Pirates become the highest bidder on a big free agent, only then will we know they mean business. For now, it’s just eye wash.

Pirates' Struggles in Recent Years

The Pirates finished the 2025 season with a 71-91 record, good for last in the NL Central Division and the fifth worst in baseball.

It served as their 10th straight season missing the playoffs and the seventh consecutive losing season, both the second longest streaks in baseball, just behind the Los Angeles Angels.

The Pirates have had just four winning seasons in the past 33 years since 1993, which saw them suffer 20 consecutive losing seasons, a North American Professional Sports (MLB, NBA, NFL, NHL) record.

Pittsburgh saw a brief history of success last decade, with three straight postseason appearances from 2013-15 and pushing the St. Louis Cardinals to five games in the 2013 NLDS, but that's all the winning most Pirates fans have seen.

Pirates' Lack of Spending in Free Agency

Pittsburgh is historically a team with one of the lowest payrolls in baseball and one that rarely makes moves in free agency,

The Pirates haven't signed a free agent position player to a multi-year deal since outfielderJohn Jaso, two-years, $8 million on Dec. 23, 2015. Their most recent free agent multi-year signing was starting pitcher Iván Nova for three years, $26 million on Dec. 27, 2016.

Pittsburgh's record free agent signing is a three-year, $39 million deal for left-handed pitcher Francisco Liriano, which he signed on Dec. 9, 2014.

Bob Nutting has served as the primary owner of the team since 2007 and the Pirates have ranked in the bottom five MLB teams for Opening Day payroll for 16 of those 19 seasons, according to Cot's Contracts.

The Pirates have a record of 1354-1619 (.455) under Nutting, with just those three playoff appearances from 2013-15 and four winning seasons in 19 years in charge.

Why These Matter This Offseason

Pittsburgh has a great pitching staff, with NL Cy Young Award winner Paul Skenes leading the way.

The Pirates also have some promising rookies like Braxton Aschraft, Hunter Barco, Mike Burrows and Bubba Chandler, along with a good bullpen, that finished with the seventh lowest ERA (3.76) and the most shutouts (19) in baseball.

Pittsburgh was awful at the plate, with the worst slugging percentage (.350) and OPS (.655) and the least home runs (117), runs scored (583) and RBI (563) of any MLB team.

The Pirates targeted players like Naylor and Schwarber to fix those roles, but now have to pivot elsewhere.

Some other free agents they've looked at include second baseman Jorge Polanco, slugger Ryan O'Hearn and Japanese superstars in Munetaka Murakami and Kazuma Okamoto, who have all shown power in their past.

One reason why the recent struggles hurt the Pirates is with Polanco, who reportedly would spur a better offer to go play with a competitor.

This may cause the Pirates to shift towards the trade market, where they look at the likes of second baseman in Tampa Bay Rays' Brandon Lowe and New York Mets' Jeff McNeil, plus Arizona Diamondbacks' Ketel Marte.