What was supposed to be a promising first offseason under new owner David Rubenstein instead just feels like more of the same for Baltimore Orioles fans.

While signing slugging outfielder Tyler O’Neill to a three-year, $49.5 million contract is worthy of acknowledgement, the organization has failed to extend its current star players or acquire new ones who could inch the team closer to title contention.

A possible Jack Flaherty reunion might show people that Rubenstein is serious about building on the Orioles’ consecutive playoff appearances.

The World Series champion is among the best starting pitchers left in free agency, which makes him a coveted commodity for a ballclub that is constantly facing injury and depth concerns in its rotation.

But the fan base should temper its enthusiasm, or tone down its dread, depending on how one feels about Flaherty. A Baltimore insider is pouring cold water on a potential return to Camden Yards.

“I would actually kind of be surprised if Flaherty came back to the Orioles,” Rich Dubroff of BaltimoreBaseball.com told “Foul Territory.” “He didn’t have a good time there. He was there for the last two months of {the 2023 season} and he didn’t pitch well. If he’s asking for a five-year deal, I don’t know that they’re going to be interested. I think they’d rather go the trade route.”

Orioles saw Jack Flaherty as a potential X-factor in the past

The O’s added Jack Flaherty from the St. Louis Cardinals at the 2023 MLB trade deadline, in an effort to capitalize on their rapid rise in the American League.

The move did not pay off, as the former first-round draft pick posted a frightful 6.75 ERA in nine regular season games for Baltimore. He also underwhelmed in his playoff outing, allowing one run, two hits and three walks in two innings of relief work versus the eventual champion Texas Rangers.

Flaherty flipped the switch last season, though, drawing closer to his peak 2019 form (finished fourth in Cy Young voting). He recorded a 3.17 ERA with 194 strikeouts across his stints with the Detroit Tigers and Los Angeles Dodgers in 2024. And although his October stats were overall abysmal– 7.36 ERA in five games– Flaherty provided LA with key starts and innings during the title run.

The Orioles could be hoping that he can fill a similar role for them in 2025. Corbin Burnes’ departure, besides being a big blow to the franchise’s possible plan to become major free agency players, leaves a massive void for management to fill at the top of the pitching staff.

Whether or not Jack Flaherty is the one to occupy that role, Baltimore will probably need to take action this winter if it intends to win its first AL pennant in 42 years. Patience is thinning in Charm City.