The San Francisco Giants just lost Pablo Sandoval, their third baseman and cleanup hitter. So, naturally, they should set their sights on…Jon Lester, starting pitcher.

Seems counterintuitive on its face. Sandoval’s departure leaves a panda-sized hole in the San Francisco lineup; shouldn’t filling it be priority No. 1?

The Giants must pursue offensive upgrades, no argument there. In addition to replacing Sandoval, they need a left fielder and complementary pieces to bolster the bench.

But first they should take the gobs of cash they were prepared to hand Sandoval—$95 million over five years, as general manager Bobby Evans revealed on Yahoo SportsTalk Live, per CSN Bay Area—and use it to woo Lester.

If they do land him—and, according to Nick Cafardo of The Boston Globe, they’re “becoming more serious” in their pursuit—it’ll cost them the Sandoval money and then some.

Lester, the top arm on the market not named Max Scherzer, just enjoyed another typically stellar season: 2.46 ERA, 219.2 innings pitched, 220 strikeouts and a 1.102 WHIP.

Naturally, the Giants aren’t alone in the Lester sweepstakes: The Chicago Cubs, Atlanta Braves and Boston Red Sox have also been linked to the 30-year-old left-hander, per CBS Sports’ Jon Heyman. Expect every team with dough to burn to at least kick the tires.

Giants fans mulling a potential Lester signing may recall the last time San Francisco inked an Oakland A’s left-hander to a massive pact…a fella by the name of Barry Zito.

While Zito ultimately redeemed himself with a gutsy renaissance in the 2012 postseason, helping the Giants secure the second of their three recent rings, his tenure in San Francisco was generally unremarkable and intermittently awful.

So there are reasons to be cautious. As Grant Brisbee of McCovey Chronicles put it, “Lester makes me mighty nervous. At least he’s actually good, though, and not smoke-‘n’-mirrors good like Zito was in his last two years with the A’s.”

Frayed nerves and scarring memories aside, let’s look at what Lester would do for San Francisco.

For all the hand-wringing over Sandoval, the Giants’ true Achilles heel is the starting rotation.

Yes, Madison Bumgarner, fresh off his historic playoff dominance, is an unmitigated stud. After that, things get dicey in a hurry.

Veteran Tim Hudson had a nice year, but he struggled down the stretch, posting an unsightly 8.72 ERA in September, and he turns 40 in July.

Matt Cain, once the sort of horse you’d hitch a franchise to, is recovering from season-ending elbow and ankle surgery.

After that, the Giants have journeyman Yusmeiro Petit, who lifted his stock with a superlative October, and former ace Tim Lincecum, coming off a third consecutive (mostly) dreadful season.

Now imagine Lester slotted next to Bumgarner, creating one of the most formidable left-handed tandems in baseball. Instantly, San Francisco’s starting corps goes from a potential weakness to a significant strength, especially if Cain returns to form.

Yes, a five- or six-year deal would carry Lester at least into his mid-30s. But he’s defined durable, tossing more than 200 innings in six of the last seven seasons.

And he’d play his home games at AT&T Park, an extreme pitchers’ yard.

Of course, the Giants could wow Lester with a budget-busting offer and still lose out. He’s got deep ties to the Red Sox, his old team, as Heyman notes.

He’s also familiar with Cubs president of baseball operations Theo Epstein, who was general manager in Boston when Lester made his big-league debut, and he makes his home in Atlanta.

“When you get to a certain point, money can’t buy happiness,” Lester said of his prospective landing spots, per Heyman.

That seems to suggest he’ll prioritize an ideal location over a maximum payday. Then again, he’s yet to sign, indicating he’s at least weighing all options.

If he chooses the Giants, he’ll nudge the defending champs closer to another title and give himself a chance to improve upon his impressive 2.57 career postseason ERA.

If he goes elsewhere, San Francisco will have to keep scrambling to plug its many holes…and spend that Pablo money.


All statistics courtesy of Baseball-Reference.

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