Los Angeles Dodgers
Flaherty grew up in SoCal, and speculation long has had him returning to the Los Angeles area once he became a free agent. This deal would get him there just a few months earlier than expected.
The Dodgers have suffered plenty of starting pitcher injuries. Walker Buehler was known to be out at least most of the year, while Julio Urias, Clayton Kershaw, Tony Gonsolin, Noah Syndergaard, and Ryan Pepiot all have missed various lengths of time due to injuries. The result has been lots of rookies - mostly Bobby Miller, Gavin Stone, Michael Grove, and Emmet Sheehan - taking turns in LA's rotation.
The results have been a mixed bag, with Miller and Sheehan being around average, Grove being bad, and Stone being horrendous, at least when looking just at ERA. Certainly, the small number of innings each has thrown are not enough to judge any of them as long-term assets.
Still, if you're the Dodgers, who are in the playoff hunt every single season, waiting for young pitchers to figure things out at the big league level isn't enough. Bringing in reinforcements from outside the organization will be a priority for LA as the trade deadline approaches. Flaherty certainly would help the Dodgers content for a National League West title. The question is, what would LA be willing to surrender to make a trade happen?
First, let's consider if there's a way to sweeten the appeal of a deal. With Gavin Lux lost to injury for the entire season, the Dodgers also could use help at shortstop, someone who would be a step up from Miguel Rojas. What do you know, the Cardinals just happen to have Paul DeJong available, and if St. Louis would be willing to eat some of his salary, they could improve the package they get in return for a combined Flaherty-DeJong duo.
The Cardinals desperately need starting pitching. Miller is not a realistic return, but one of Sheehan, Grove, Stone, or Pepiot should be options, and the Dodgers have so much depth in their farm system, plucking another 1-2 minor league lottery tickets should be feasible.
Some may look at these pitchers' major league performances to date and scoff at such a weak return for a rental of a mid-tier starter and a new starting shortstop. But keep in mind, even Greg Maddux had a 5.59 ERA in his first two seasons. Of course, the odds of any of these pitchers - or any pitcher anywhere - performing close to Maddux's level are essentially zero. The point is, a small number of innings early in a pitcher's career aren't enough to make a solid judgment.
Flaherty would feel right at home in Dodger Stadium, and DeJong would help on both sides of the ball. Getting a potential rotation piece for 2024 and beyond would be mandatory for the Cardinals in a deal like this.