Jack Flaherty risks making same mistake twice despite lack of Cardinals involvement

As Blake Snell, Max Fried and Nathan Eovaldi find long-term deals, Garrett Crochet finally gets dealt and rumors swirl around big names like Corbin Burnes and Luis Castillo, it seems like the only pitcher who hasn't been able to build a market this winter is former Los Angeles Dodgers righty Jack Flaherty.

Flaherty seemed to have put himself in good position to cash in, excelling with the Detroit Tigers early in 2024 before helping pitch L.A. to the World Series after a trade deadline deal. But he looked to be running out of steam late in October, and he got lit up in his final appearance in Game 5 against the New York Yankees. Combine that with some well-documented health concerns, and suddenly it's an open question whether any team is going to be willing to shell out big-time cash for Flaherty's services.

Things have gotten so desperate that, according to recent reports, Flaherty might be considering a reunion with a former team that finds itself in need of a starter. No, not the St. Louis Cardinals — the Baltimore Orioles.

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Jack Flaherty emerges as 'fallback option' for Orioles

The latest update on Flaherty comes via The Athletic's Ken Rosenthal, who reports that the right-hander is "one fallback option for the Orioles if, as expected, they fail to re-sign Corbin Burnes." Burnes' market appears to be in the stratosphere as teams like the San Francisco Giants and Toronto Blue Jays get desperate with the last big-name starter available, but the fact that Flaherty might be a fit in Baltimore comes as a shock. The O's made Flaherty their big deadline acquisition back in 2023, only to watch him pitch to a 6.75 ERA down the stretch and fail to earn a spot in the team's postseason rotation.

According to Rosenthal, however, GM Mike Elias may be willing to give Flaherty a pass for the bad first impression. "Flaherty already had thrown 109.2 innings after combining for only 154.2 the previous three seasons due to injuries," Rosenthal writes. "The Orioles were not necessarily surprised when he stumbled ... But in a limited market, few better options were available."

If team was going to make an ill-advised reunion with Flaherty this winter, the smart money would've pegged the Cardinals, who could certainly use the rotation help in 2025. But it seems as though there were enough red flags surrounding the 29-year-old's profile that he's resigned to waiting out the rest of the market and seeing which team(s) is left. It's quite the fall for a guy who looked to have resurrected his career this season.