3 doomsday Jack Flaherty destinations to get long-awaited revenge on Cardinals

The Los Angeles Dodgers are on the cusp on a World Series victory, which means Jack Flaherty will end the season as world champ. After his disastrous postseason stint with Baltimore a year ago, this has to feel especially good for Flaherty. The job isn't done yet, but the New York Yankees appear dead in the water. It would take a minor miracle for the Dodgers to fumble their 3-0 lead.

Flaherty has been largely impressive this October, helping the Dodgers maintain excellence without Tyler Glasnow, Shohei Ohtani, Clayton Kershew, or Bobby Miller in the postseason rotation. Los Angeles' ability to persevere through so many injuries to the pitching staff is remarkable, and it's a major credit to the job Flaherty has done since landing with his hometown team at the trade deadline.

These last couple years have been quite eventful for Flaherty. He began the 2023 campaign in a St. Louis Cardinals uniform, only to wind up with Baltimore at the trade deadline. Then, he started 2024 with the Detroit Tigers, before getting dealt again at the deadline. This time Flaherty landed with the Dodgers, the team he grew up rooting for. It has been a special run, one that clearly means a lot to Flaherty personally.

That said, his performance this October could price him out of a new contract with the Dodgers, especially if LA focuses its resources on more established aces, such as Max Fried or Blake Snell. The Dodgers were also recently connected to Juan Soto, so Flaherty does not feel like a top priority.

He could use this free agency period to exact his long-gestating revenge on St. Louis. The Cardinals clearly missed Flaherty after the initial trade and, as if winning a World Series in Dodgers blue wasn't revenge enough, there's a decent chance he ends up in a unique position to torment the Cardinals moving forward.

Here are a few realistic landing spots that St. Louis fans (and Dodgers fans, for that matter) will be rooting against.

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3. Jack Flaherty could help Terry Francona revive the Reds

The Cincinnati Reds finished last season eight games below .500 in an extremely competitive NL Central. That is six games behind the second-place Cardinals, who appear committed to a slow and patient rebuild moving forward. The Reds are committed to no such plan, instead vowing to take the next step with a new manager.

Cincy lured Terry Francona out of retirement in one of the offseason's most stunning developments. The two-time World Series champ and three-time Manager of the Year will have a pretty clear directive in Cincinnati: take this young, upstart group to October. There's no reason to believe he can't or won't accomplish that.

This Reds roster is quietly impressive. Sure, it needs a bit more stability, but that's what free agency is for. Take for example the rotation, where Flaherty would join a group that already includes Cy Young candidate Hunter Greene and the highly intriguing 22-year-old Rhett Lowder. Cincinnati was battered by injuries to the pitching staff last season, but return that group to full strength, add Jack Flaherty, and suddenly the Reds stack up quite nicely with a winnable division.

Elly De La Cruz is a year or two away from receiving legitimate MVP votes, if that. This Reds team is very much trending up, in the opposite direction of St. Louis. If Flaherty can bring his worldly experience and newfound postseason confidence to the Reds rotation, that's a recipe for success.

2. Jack Flaherty in a Brewers uniform is the last thing Cardinals fans want to see

The Milwaukee Brewers made it to the playoffs with home-field advantage, but couldn't field enough quality pitching when it mattered most. That explosive New York Mets offense put Milwaukee in an early grave, once again raising questions about the postseason viability of this Brewers core.

Trading Corbin Burnes certainly didn't help, but the Brewers aren't in the practice of dropping $200 million-plus contracts. Now Willy Adames threatens to leave, meaning Milwaukee's tenure atop the NL Central is teetering rather precariously on the brink. There's room for Chicago, Cincinnati, even an unsuspecting St. Louis or Pittsburgh, to break through. That is, unless the Brewers operate with the necessary aggression to build out this roster.

Flaherty would give the Brewers a workable front-line ace to lead the rotation. Freddy Peralta, Frankie Montas, and Colin Rea are all free agents, so the Brewers will need to work overtime to either piece this rotation back together or to field a brand-new unit. Regardless of which path the front office ultimately takes, paying the extra buck to land Flaherty would give Milwaukee much-needed stability.

This move also helps the Brewers on multiple fronts, keeping Flaherty away from fellow NL contenders, like the Mets or Dodgers. Milwaukee should still be operating as the preseason favorite to win the division, which means planning ahead to October.

1. Jack Flaherty would give the Cubs the perfect Kyle Hendricks replacement

The Chicago Cubs are looking to level up after back-to-back 83-win seasons. Craig Counsell has said he expects more from this group, which reads as a direct challenge to Jed Hoyer and the front office. Chicago is never going to break the bank relative to other top-market contenders, but the Cubs do have enough resources to meaningfully build out and improve this roster.

Several lingering questions face the Cubs this offseason. What happens with Cody Bellinger and his opt out? And, by extension, how will Hoyer handle the oncoming free agency deluge? The Cubs' GM has made it clear that he is building with the future in mind, but that shouldn't prevent Chicago from seeking out immediate roster upgrades.

The pitching staff was a relative bright spot for the Cubs last season, at least in the starting rotation. That said, Javier Assad's production curtailed late in the campaign and Kyle Hendricks is destined for a new home after more than a decade at Wrigley Field. The Cubs would benefit from a proper third ace to spearhead the rotation alongside Justin Steele and Shota Imanaga. Flaherty would give Chicago postseason experience and, potentially, the small boost needed to reach October.

Obviously, the Cardinals will hope that Flaherty lands somewhere outside the division, ideally away from the Dodgers, too. With so much positive momentum building around the NL Central, however, don't be surprised if Flaherty ends up on the opposite end of a heated Cardinals rivalry in a few months time.