5 biggest regrets the Giants should have this offseason

Nick San Miguel
Former Giants pitcher Madison Bumgarner. (Photo by Jason O. Watson/Getty Images)
Former Giants pitcher Madison Bumgarner. (Photo by Jason O. Watson/Getty Images) /
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San Francisco Giants
Former Giants pitcher Madison Bumgarner. (Photo by Thearon W. Henderson/Getty Images) /

Not pursuing Madison Bumgarner hard enough

We all knew that Madison Bumgarner would likely not be with the Giants in 2020, but the front office should have tried harder than they did to prevent him from leaving.

He ended up signing with the Arizona Diamondbacks on a five-year, $85 million deal. The Giants offered him a four-year deal at around $70 million. He wanted a longer deal and the D-backs gave it to him.

Still, there has been a lot of speculation that Bumgarner wanted to stay in San Francisco. At the very least, if the Giants had offered him the exact same contract and he still signed with Diamondbacks, we all could have moved on and understood that he was ready for a chance.

Instead, there will always be a lingering: “What if?”

In a perfect world, he would have remained with the Giants for life, maybe even retiring at the same time as his longtime battery-mate Buster Posey after storied careers that turned them into Bay Area legends.

Alas, that dream is dead. Now the Giants are left with a shell of a rotation that lacks a clear ace and has no clear-cut future ace within the organization.

The Giants could have known who their Opening Day starter would have been for the next five years if they gave Bumgarner the deal he received from the D-backs. Instead, they chose uncertainty. We’ll see if that was the right move.