MLB insider's latest Pirates free agency backup plan still sounds impossible

The Pittsburgh Pirates have a problem. Despite an increased budget, the club is having a hard time finding someone to take their money. Pittsburgh might have been serious about Josh Naylor, but the Seattle Mariners' first baseman wasn't serious about Pittsburgh, agreeing to terms to go back to the Pacific Northwest before Ben Cherington could finalize a formal offer.

While their $120 million offer to Kyle Schwarber would have easily eclipsed Francisco Liriano's franchise-record $39 million free agent contract, it's hard to say that was a serious offer either.

Former MLB general manager Jim Bowden explained why while appearing on Foul Territory this week. According to him, no top-tier free agent is going to take an offer from Pittsburgh seriously unless it blows the competition out of the water.

In the same breath, Bowden proposes a backup plan for the Pirates that he thinks could work — go out and sign Ryan O'Hearn and Eugenio Suarez. Those wouldn't be terrible additions, but there's something Bowden is still missing.

Jim Bowden's Pirates backup plan of Eugenio Suarez and Ryan O'Hearn will fail for the same reasons their pursuits of other top free agents did

While O'Hearn and Suarez aren't in the Schwarber-tier of free agents, they're no slouches themselves. Both were in-demand pieces at the trade deadline, and both landed with contenders; O'Hearn in San Diego and Suarez in Seattle, getting a chance to taste October baseball.

There are a plethora of contenders who could still use their services this winter as well. For example, Suarez was originally a Detroit Tigers farmhand, and they conveniently have an opening at third base, as well as a need for a power bat in the middle of their lineup this offseason. O'Hearn could be a first base/DH upgrade for numerous contenders as well.

So, back to Bowden's original point: why would either sign with Pittsburgh unless it was for a massive overpay? Furthermore, while you can talk yourself into an overpay for a franchise-changing bat like Schwarber, the stretch gets that much tougher to complete when you move down to the mid-tier where these two reside.

There's a little bit more here, though. This isn't just about small markets. The Minnesota Twins are a small-market team, but they've still nabbed some big fish over the years. If the Tampa Bay Rays ever wanted to open the checkbook, they'd surely be able to convince a top-tier option to join their organization.

The reason for that is, despite financial limitations, those two franchises have shown a commitment to winning. They invest in player development, analytics, and whatever else on the margins can give them an edge. As a result, they jump into the fray with the big-money contenders every so often.

The Pirates? Their own players treat the organization like a joke. Don't think for a second that word of how the current players truly feel about the club doesn't get passed around the league.

Until the Pirates fix their reputation as an unserious organization, no one is ever going to trust them enough to sign there unless it is a massive overpay. Let's be real. Even with this windfall being added to the budget for 2026, players have to be thinking that if Bob Nutting doesn't see the returns he'd like on that investment, he'll slash payroll again to the bone in 2027. Why then would anyone risk sticking themselves in baseball purgatory during their prime earning years unless they were being vastly overpaid?

The Pirates have an image problem, and until they can sufficiently address that, they're going to be stuck between massive overpays or gigantic whiffs on the free-agent front.