5 biggest regrets the Giants should have this offseason

The San Francisco Giants had a slow offseason while waving goodbye to three of their best players from 2020. What are their biggest offseason regrets?

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Former Giants pitcher Madison Bumgarner. (Photo by Jason O. Watson/Getty Images)

Spring training is nearly upon us which means that the offseason will fade into the background as we get closer to games that count. Before it becomes a distant memory, we should examine what the biggest regrets are for the San Francisco Giants this offseason.

With numerous holes on the roster and weaknesses across the board in the lineup, rotation and bullpen, there are plenty of potential regrets. That to make no mention of a dissatisfied fan base.

The current state of the team leaves a lot to be desired, and while the Giants probably could not have turned themselves into a contender over the course of a single offseason, they definitely left some gaping holes that do not seem likely to be filled by younger talent any time soon.

Some will argue that is the point. If 2020 is going to be a rebuilding year, roster holes are to be expected from a team that does not have plans on contending in the near future.

Others will say that professional sports teams should try to win no matter the current state of the franchise and that the team should continually be looking for ways to better the roster.

It is clear what path the Giants chose, but there were several moves they could have made this offseason that would not have sacrificed their future while still improving the on-field product in 2020.

So let's take a look at five regrets the Giants should have from this offseason.

Not pursuing Madison Bumgarner hard enough

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Former Giants pitcher Madison Bumgarner. (Photo by Thearon W. Henderson/Getty Images)

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.

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Not bringing back Kevin Pillar

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Former Giants outfielder Kevin Pillar. (Photo by Jason O. Watson/Getty Images)

The Boston Red Sox just signed Kevin Pillar to a one-year, $4.25 million deal. The Giants did not want to pay Pillar $10 million in arbitration, but they could have gotten him for a discounted price.

If they non-tendered him but then began to negotiate, he almost certainly would have taken a one-year deal in the $6-7 million range, understanding that he would be the starting center fielder and knowing that he was a respected leader after winning the Willie Mac Award.

Now the Giants go into the season without a clear center fielder. If Zaidi didn't want to pay Pillar the $10 million, that's fine, but he still could have brought back a solid player who led the team in most major offensive categories last season.

Again, he chose uncertainty over a proven commodity. Maybe it will pay off in the long run, but it won't make things any easier in 2020.

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Not signing a power bat

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Giants offseason target Nicholas Castellanos. (Photo by Dylan Buell/Getty Images)

One of the major priorities Farhan Zaidi laid out at the beginning of the offseason was to acquire a power bat. Unless you consider Hunter Pence and Pablo Sandoval power bats, it is safe to say he failed.

Despite being linked to slugger Nick Castellanos, the Giants were unable to seal the deal and ink the powerful hitter to a contract.

We know that it is difficult to attract big free-agent hitters to the Giants for a multitude of reasons, but with the dearth of power that exists on the roster, you would have thought that Zaidi would have made a bigger push to provide some pop to the lineup.

Perhaps the team was a bit gun-shy after being spurned the past two offseasons in their pursuit of Giancarlo Stanton and Bryce Harper.

Regardless, now the best power hitter on the team is probably Evan Longoria. If you gulped just reading that sentence, I can assure you that I gulped even harder writing it.

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Not signing a closer

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Giants offseason target Daniel Hudson. (Photo by Rob Carr/Getty Images)

The Giants were fortunate enough to have one of the best closers in baseball last season.

Left-hander Will Smith had 34 saves last season with a 2.76 ERA and 96 strikeouts in 65.1 innings, and he was the team's representative in the All-Star Game.

As expected, he departed for greener pastures in free agency, signing a three-year, $40 million deal with the Atlanta Braves.

However, the Giants failed to find a proven replacement, and it looks like they will instead turn to veteran setup man Tony Watson to fill the ninth-inning void.

There were solid options on the free-agent market like Daniel Hudson and Steve Cishek who would have at least given some measure of stability to the back-end of a weak bullpen.

If the Giants can't rely on Watson to close out games, things could go from bad to worse awfully quick in 2020.

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Leaving the fan base despondent

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Giants fans. (Photo by Lachlan Cunningham/Getty Images)

San Francisco Giants fans were spoiled for most of the 2010s.

We got to see our favorite team win three championships in a five-year span, accruing memories that will last a lifetime. So despite the fact that we're still basically playing with house money, it isn't fun to watch your team be bad.

The departure of longtime manager Bruce Bochy, then longtime ace Madison Bumgarner, coupled with the questionable hire of Gabe Kapler really just wore down the fan base as the offseason progressed.

We knew it was coming, but that didn't make it any easier.

The front office no doubt sensed that dissatisfaction, and that could be why they decided to bring back two beloved Giants in Hunter Pence and Pablo Sandoval.

It's kind of like how on the T.V. show The Office, Will Ferrell made a few guest appearances right as Steve Carrell was leaving the show to make that transition a little easier. Sandoval and Pence are Ferrell in this scenario. Kapler is probably Robert California.

While the nostalgic signings have appeased the fan base to a point, it doesn't change the fact that the Giants are unlikely to contend in 2020.

Next: 5 biggest Giants spring training storylines

When teams rebuild, they are usually bad for a while. So while there may be some regrets from this offseason, hopefully it is in the service of future success.