The Chicago Cubs head into the offseason looking to improve their weaknesses and bolster their strengths, just like every other team in Major League Baseball.
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So, a couple of things. First off, if the Dodgers starting rotation can get healthy, and it's admittedly a big question mark, losing Flaherty wouldn't be a huge loss for them (but it would definitely hurt some). Next year, they will have Ohtani, Glasnow, Yamamoto, May, Gonsolin, Kershaw, and Buehler. While Kershaw may be finished, I wouldn't count him out just yet. That being said, he certainly can't be counted on to be injury free.
Here's the other thing. Rumor has it that the Dodgers have their eye on Roki Sasaki. For those of you who aren't familiar with him, he's probably the top pitcher in Japan and appears to want to play in the MLB. He's believed to have a contract that allows him to choose where he wants to play. He's 22, has a 100MPH fastball, a 92MPH splitter with about a 30 inch drop, strikes out about 13 batters per 9 innings, walks about 2, has a WHIP under .8, and a 1.7 ERA.
At his age and experience level, he would probably get in the neighborhood of 30M per year and he would probably be most comfortable in Dodger blue. So, yeah, Flaherty is a valuable pitcher and would be a good fit for the Cubs, but I think the Dodgers are so deep in starting pitching that it wouldn't be a disaster if they lost him. He's had a great year, but he's also had some not-so-good ones. Let's see how he does tonight. In his last start, he lost about 3-4 MPH off his fastball and didn't look very good, but he's gotten some rest and that'll hopefully give his arm a little more life.
If he can give the Dodgers a win in game 1, they'll have a huge advantage (which can disappear in one bad game....hey, it's the playoffs) going into game 2 and it'll boost his worth in the off season marketplace.
Stay tuned......
EDIT: With a healthy staff, Flaherty would be, at best, the #4 starter in the Dodgers rotation.