Retool or rebuild. That's not a question. It's a choice. If championship teams don't constantly retool, they'll be forced to rebuild (or watch other teams take a run at the championship). In baseball, the St. Louis Cardinals are the quintessential team when it comes to retooling. They never appear to intentionally engage in a rebuild, but almost every year, they're in the hunt for a playoff spot. Given that winning championships always involve a bit of luck, the more times you can make the playoffs, the more likely you'll walk away as champs from time to time. It's no accident that the Cardinals have won 11 World Series titles, which ranks second only to the Yankees, a team that historically has operated with far larger budgets than the Cardinals.
Much to the chagrin of Giants fans, in recent years, the Dodgers have become experts at retooling. They've won six National League West titles in a row (2013-2018) and appear to be well on their way to a 7th. And while there has been some continuity in terms of players from year to year, there are only a couple on this year's team who were on the 2013 team. The only consolation for Giants fans in the face of this dominance is that the Dodgers have yet to claim a World Series title.
By contrast, the Giants have failed in their attempt to retool. They held on to players too long and traded away prospects for older players in the hope of making another run at a pennant. Now, they've been forced to rebuild, and will soon be unloading top pitchers like Madison Bumgarner and Will Smith with the goal of acquiring future prospects. Moreover, it looks like it won't be until 2021 that they become serious contenders again. It is possible that they could surprise everyone in 2020 if a few prospects pan out sooner and/or better than expected, but few of us are holding our breath. Then again, 2020 is an even year...
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