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Red Sox saved from David Hamilton WS hero narrative as Caleb Durbin trade takes late twist for Brewers

The trade that keeps on giving.
ByBrandon Glick
Milwaukee Brewers third baseman David Hamilton.
Milwaukee Brewers third baseman David Hamilton. | IMAGN IMAGES via Reuters Connect

If you didn't tune in to last night's World Series game, I wouldn't blame you; the Boston Red Sox have been out of this thing for a while, and the odds facing their division rival, the Tampa Bay Rays, to make a comeback from down 3-0 are... well, they're not great.

If you turned off Game 4 of the World Series after David Hamilton hit a fifth-inning home run to tie the game -- immediately making up for his uncharacteristic throwing error in the fourth -- I really wouldn't blame you. Watching a Red Sox castoff play Fall Classic hero elsewhere isn't the most exciting thing in the world to do, and it's also not the first time this postseason that Hamilton has provided the Milwaukee Brewers with some clutch production from the batter's box.

However, if you weren't watching, you missed an all-time classic. Hamilton got subbed out for Joey Ortiz in the ninth inning as a defensive replacement (the game was tied at the time), only for the latter to make a throwing error of his own in the bottom of the 12th (now with a one-run lead). Immediately after, the Brewers inserted another former Red Sox player, Shane Drohan, onto the mound, tasking him with a simple objective: Close out the first title in franchise history.

Drohan, a starter by trade, wilted under the pressure immediately. He gave up four straight singles, yielding an extra-inning walk-off to the Rays. There's now a little life in Tampa Bay, even if a 3-1 series deficit is still darn-near insurmountable.

And somehow, for a Brewers team built on homegrown talent, it was the former Red Sox players caught directly in the spotlight.

Caleb Durbin trade takes another ridiculous twist as Shane Drohan, Brewers blow Game 4 of World Series

What's funny about all this is that Hamilton and Drohan were the "throw-in" pieces in that Sox-Brewers blockbuster back in February. Kyle Harrison was the big name heading to Milwaukee, but after a scintillating first half, he fell way off the radar down the stretch. In fact, he hasn't made a single appearance in these playoffs despite making the Brewers' roster in every round.

What is now known as the "Caleb Durbin" trade went through about as many ups and downs as you could possibly imagine in a single year, in no small part because the titular third baseman got off to a historically slow start in Boston before getting himself back on track. He should be an asset for the Red Sox for years to come, but in 2026, he combined with Andruw Monasterio and Anthony Seigler to give the team less value (3.1 fWAR) than the Brewers got from their trio (4.1 fWAR).

It's still rather likely that Harrison, Hamilton, and Drohan are all wearing World Series rings by the time this is all said and done, which is going to give the Brewers a mighty leg up in "Who won the deal?" conversations. But their collective playoff follies might create just enough of a window for the Red Sox to come from behind and at least pull even in the long run.

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