Sep 30, 2023; Pittsburgh, Pennsylvania, USA; Pittsburgh Pirates owner Robert Nutting (left) shakes hands with left fielder Bryan Reynolds (right) at the batting cage before the game against the Miami Marlins at PNC Park. Mandatory Credit: Charles LeClaire-Imagn Images Charles LeClaire-Imagn Images

Pirates Could Repeat Best Offseason From Last Decade

Originally posted on Pittsburgh Pirates on SI
By Erin Shapland | Last updated Nov 20, 2025 10:05 AM ET

The Pittsburgh Pirates have failed to spend the money necessary to land free agent talent in offseasons past, and fans expect this season to be no different. They do have yet another chance to prove their supporters wrong, however, and they might look to a productive offseason from ten years ago as a guiding light.

The Pirates' 2015-2016 offseason saw them sign their last multi-year contract with a free-agent hitter, landing them first baseman John Jaso on a two-year, $8 million contract. When the two years were up, Jaso retired from the sport. Writing for FanSided, Noah Wright recently recommended that the Pirates use that offseason as a blueprint for 2025-2026, a moment when the Pirates could turn things around with exactly the budget they intend to use.

"[...] the Pirates added three firmly above-average hitters — good enough to be semi-regulars, at the very least — and two decent middle relief pitchers, all while still on a tight budget," Wright wrote. "Jaso, Joyce, Freese, Nicasio, and Feliz made a combined $15.08 million in 2016. MLB salaries may have changed dramatically over the last decade, but this only represents about half of what the Pirates seem to be willing to spend this offseason."

"The Pirates should still be willing to add more via trade (such as a Spencer Horwitz 2.0 move). If Pittsburgh intends to be active this offseason, this is the sort of blueprint they need to run with."

Same Story, Different Offseason?

Bob Nutting, the Pirates' miserly owner, is widely anticipated to over-promise and under-deliver this offseason, given his history of doing just that. Despite his protestation that he wants to stay in Pittsburgh and win with the Pirates, superstar starting pitcher Paul Skenes is almost certain to leave the team when the time comes, as has become customary since Nutting's 2007 acquisition of the team.

Following the recent news from MLB Insider Jeff Passan that the Pirates are in the mix for star free agents like Philadelphia Phillies outfielder Kyle Schwarber and Seattle Mariners first baseman Josh Naylor, Pirates fans have reacted with skepticism and resentment at the notion that Nutting's team will once again get their hopes up and fall short.

Even in the offseason, fans are still getting their rage out. At a recent College GameDay, another plane trailing a "Set Pittsburgh Free, Bob! Sell The Team! H2P!!" (where "H2P" stands for Hail to Pitt) flew over the stadium. A fan organization with the website ourteamnothis.com has performed similar activism in the past, with a similar plane flying over PNC Park on Opening Day in 2025. Nutting could prove naysayers wrong this winter, and some are still hopeful that he will.

This article first appeared on Pittsburgh Pirates on SI and was syndicated with permission.

More must-reads: