Top Landing Spots for Free Agent Jack Flaherty

As we’ve already started to see, starting pitching will go for a premium this offseason. That goes for established arms as well as ones that just successfully reestablished their value. 

Starting pitcher Jack Flaherty falls into the latter category of starters who should get paid handsomely in the coming months. It took a strong effort from the eight-year veteran to get to that point, though. 

Injuries limited Flaherty in both the 2021 and 2022 seasons. His subpar performance in 2023 then caused the Cardinals to trade their 2014 first-rounder and one-time ace to the Orioles at that year’s trade deadline. 

That led the righty to sign a one-year, $14 million “prove it” deal with the Tigers last winter, and prove it is exactly what he did. His strikeout rate (29.9%) was back up, while his walk rate (5.2%) and ERA (3.17) were back down. The cherry on top: a midseason trade to the Dodgers that earned him a World Series ring. 

Now Flaherty finds himself as a free agent for the second straight offseason but in a much better position than last year. With multiple teams sure to bid for his services, where exactly might the 29-year-old land? 

Top Landing Spots for Jack Flaherty 

Detroit Tigers 

After seven years of watching dismal performances, Tigers fans finally had something to cheer about again in 2024. At 86-76, Detroit had its first winning record since 2016 while making the postseason for the first time since 2014. 

Of course, Flaherty himself played a huge part in that resurgence. Prior to being dealt at the deadline, he was 7-5 with a 2.95 ERA and 0.956 WHIP in 18 starts; he was easily the Tigers’ second best starter behind AL Cy Young winner Tarik Skubal. 

Tigers starters as a whole finished third in the AL and fourth in MLB with a combined 3.69 ERA. And Flaherty is the only one of Detroit’s top six starters not currently set to return for 2025. 

So why not fully run it back? 

The Tigers are on the upswing and finished just 6.5 games shy of the top of the AL Central. Detroit was the team that took a chance on Flaherty last offseason and let him get in position for a big payday. Perhaps he’ll repay the favor and come back for another round. 

Los Angeles Angels 

Although it was their first year post-Shohei Ohtani and Ron Washington’s first time managing a team in a decade, the 2024 Angels were hoping for a change from previous years of futility. 

Things did change. Unfortunately, it was for the worse. 

Los Angeles just missed having a 100-loss season, finishing at 63-99 and taking fifth in the division for the first time since the AL West expanded to five teams 11 years ago. Their 63 wins were second worst in the AL, ahead of only the lowly White Sox. 

The Angels struggled in all facets of the game, producing the third lowest offensive output in MLB at 3.92 runs per game and the fifth highest ERA at 4.56. To dig out of the cellar, they’ll need to do some roster reconstruction. 

That effort has already begun in the starting rotation. Los Angeles signed long-time former Cub Kyle Hendricks early in the offseason and brought Yusei Kikuchi into the fold last week. But even with those two additions and the other starters already on the staff, it doesn’t quite feel like the Angels have a true ace. 

Flaherty could change that. He had a better 2024 season than anyone on the Angels staff and has been deployed as a team’s ace before. Plus, he is still in his prime at 29. If Los Angeles isn’t done rebuilding its rotation, Flaherty feels like too good a fit. 

Boston Red Sox 

Speaking of a team looking for an ace, the Red Sox are another club that falls into that category. While they were a top-10 team in terms of starters’ ERA this past season, their young rotation could still use someone to lead the way. 

Similar to the Tigers, the 2024 Red Sox returned to relevance after a down period, albeit a shorter one. At 81-81, they finished third in the AL East while just missing out on the postseason, landing five games behind Detroit for the final Wild Card spot. 

There are plenty of options out there to be Boston’s new ace, though one (Blake Snell) recently came off the board. Corbin Burnes and Max Fried remain available, but both will command huge payouts. The Red Sox can afford large contracts, but how far do they want to go? 

If they lose out on the sweepstakes for either player or decide they don’t want to spend quite that much, they could turn to Flaherty instead. He would be a steadying presence at the top of the rotation and provide great guidance to a staff with a lot of youth. 

New York Yankees 

After years of spending big only to fall short of a World Series berth, the Yankees finally cracked the code in 2024. They made it to the Fall Classic for the first time since 2009 only to win just one game in a series loss to the Dodgers. 

We all know that the Yankees are never afraid to spend money in order to be competitive. But after coming so close to the finish line last season, their motivation to cut checks this offseason may be even higher. 

For all the things that New York did well in 2024, the starting pitching was just okay. The Yankees finished 11^th in MLB in starters’ ERA at 3.85 while giving up 3.17 walks per nine innings, eighth most in the league. 

If the Yankees want to chase after one of the big names like Burnes or Fried they almost certainly can. But instead of handing out another mega contract, paying for Flaherty is the kind of move that might be expensive for most other teams but would be easy for New York to handle. 

Texas Rangers 

In 2024, the Rangers set off to build upon the first championship in franchise history. Disappointment followed as the second-most injured team in baseball by games missed followed up a World Series victory with a 78-84 record and a missed postseason. 

Starting pitching was one of many reasons for their rough season. Rangers starters finished 21^st in MLB with a 4.35 ERA as the trio of Jacob deGrom, Max Scherzer, and Tyler Mahle pitched in just 15 games combined. 

While deGrom and Mahle will return for 2025, the Rangers lost a ton of other starting pitching depth to free agency. Scherzer, Nathan Eovaldi, Andrew Heaney, and Michael Lorenzen all hit the market this offseason. 

The Rangers may want to start handing the reigns to some of their talented young arms but would be well-advised to also shore up the rotation while they do so. Bringing in a pitcher like Flaherty could help do just that.