Giants Make Like Spider-Man, Extend Webb

On Friday, the Giants announced a five-year, $90 million contract extension with star right-hander Logan Webb. The 26-year-old Webb came to national attention during the 2021 NLCS, in which he allowed a single run across two starts against the Dodgers, striking out 17 and walking one over 14 2/3 innings. Across 2021 and 2022, Webb was 12th in baseball in pitcher WAR, one spot behind Gerrit Cole, and 20th in ERA among pitchers with at least 200 innings pitched, one spot ahead of Shane Bieber.

Webb was due to reach free agency after the 2025 season. This contract will buy out his two remaining arbitration years for a total of $20 million, then pay him $23 million, $23 million, and $24 million from 2026 to 2028. It’s a deal indicative of Webb’s special status in the Giants’ organization, and it could nonetheless be an enormous bargain for the team.

The Giants of the early 2010s had one of the strongest team identities in all of baseball, and Webb’s emergence in 2021 signified the start of the era that would succeed the heyday of the title-winning core. The only holdover from the World Series-winning years is Brandon Crawford, who might not still be around himself had he not posted a career year out of nowhere in 2021 at the age of 34. New blood has taken over, and the Giants have remade themselves in an interesting fashion.

After near-misses at signing Aaron Judge and Carlos Correa this offseason, the Giants have one of the most egalitarian wage structures in baseball. They have 10 players — 11 if you fold Webb’s extension onto his current one-year, $4.5 million salary — on contracts worth $10 million per year, but none on contracts with an AAV of $20 million or more. The default mode of building a contender is to sign a few superstars to hugely lucrative contracts and fill out the rest of the roster with pre-arbitration youngsters. The greatest bargains are to be found at the very top and very bottom of the league’s payroll list.

The Giants, by contrast, have operated almost entirely in the treacherous waters of second-tier free agents: Michael Conforto, Mitch Haniger, Sean Manaea, Ross Stripling. One way to interpret San Francisco’s roster is that a team of above-average players will produce an above-average win-loss record. And while more star-reliant teams can be thrown into crisis by one or two injuries, the Giants have strength in depth.

Another advantage to this kind of roster is that individual players can be changed out easily if they underperform or an upgrade comes available. The Giants are the fifth-oldest team in baseball, and their estimated payroll of $194 million ranks 11th. But until Webb’s extension, they had $0 committed to their payroll beyond 2025. Only four other teams could say the same, and two of those — the Reds and Athletics — are only technically major league clubs at this point.

The Giants are now committed to Webb three years longer than they’re committed to any other player. The guarantees of $23 million and $24 million in Webb’s free agent years are the three greatest single-season guarantees on San Francisco’s books currently; in fact, no Giants player has ever made $23 million in a season before. (Buster Posey, Matt Cain, Barry Zito, and Barry Bonds all topped out between $20 million and $22.18 million in their highest-paid years. And the five-year, $90 million figure must be lucky in San Francisco, as the Giants had previously signed Bonds and Hunter Pence to contracts of that length and value.)
All this is to say that the Giants seem to think Webb is special. The Giants have a relatively flat salary structure not because the team is unwilling to spend on principle, but because they’ve been unable to either develop or attract the kind of star players who go for $300 million in total value. Missing out on Judge and the breakdown of the Correa contract is unfortunate, but it’s important to stress how much of an outlier Webb has been.

From 2006 to 2009, the Giants spent consecutive top-10 picks on Tim Lincecum, Bumgarner, Posey, and Zack Wheeler. Since 2010, only two players the Giants drafted in the top 10 rounds have made an All-Star team: Joe Panik and Bryan Reynolds. So, not a lot of benefit to the Giants there now. Webb is the best homegrown Giants player since Crawford and Brandon Belt, who debuted in 2011. Barring an unexpected MVP-type season by someone like Conforto, Webb is the Giants’ best player at any position right now, and certainly their best starting pitcher.

In extending Webb now, the Giants avoid the kind of unpleasantness that Corbin Burnes experienced in his arbitration case with the Brewers. They keep Webb under contract through his age-31 season, and at a reasonable price. Webb would have had to wait another two seasons after this in order to test the market after his age-28 season. The going rate for a pitcher of Webb’s quality at that age, right now, is five or six years at between $20 million and $25 million a year. And given the flurry of post-lockout free agent activity we saw this past winter, that price could well be on the rise.

So the Giants locked in their best pitcher for 2026 to 2028 at 2022 prices, and they did so without having to commit to paying him a star’s salary through his mid-30s. The only downside from their perspective is the risk of regression or injury, the likelihood of which approaches 100% for a young pitcher over a given six-year time frame. Such is the nature of the business.

If teams are right to fear the long-term uncertainty of pitchers, the pitchers themselves must be even more concerned. After all, a few lost tens of millions is of little concern to someone who’s rich enough to own a baseball team; Webb will more than triple his career earnings with his $4.5 million salary in 2023. That’s hardly enough to set him up for life in case of (burns incense, touches wood, faces the sun and asks for divine protection) something like thoracic outlet syndrome.

This imbalance of risk is an insidious structural factor baked into the current system of baseball economics. Teams leverage it to get their players to sign below-market extensions all the time. Is Webb’s contract below-market? Sure, even taking into account that it includes two seasons in which his salary would be depressed by arbitration. But all things considered, he’s done pretty well:

I think Webb is an absolute killer, but he’s still building a track record; he’s only made 30 starts once, and the sum total of his individual accolades amount to one fourth-place Cy Young vote. And compared to what guys like him were getting through 2022, he did well even accounting for the hometown discount.

With that said, the opportunity cost for Webb in the next three years is significant. Carlos Rodón’s contract suggests that the 2022-23 offseason truly did reset the market, but we won’t know for sure until we see what the likes of Aaron Nola, Julio Urías, and Blake Snell get in free agency this coming winter. It’s also not unreasonable to expect that Webb will join the hallowed inner circle of perennial Cy Young contenders.

Webb certainly entered this season as a dark horse Cy Young candidate, and his bloated ERA through three starts owes less to any kind of collapse than an early-season glut of home runs allowed. But that’s what happens when a pitcher runs into Aaron Judge and then Max Muncy, who’s better than Judge when he’s playing in San Francisco. Webb’s HR/FB rate will drop back below 30% soon enough.

Regardless, in a best-case scenario, Webb will finish this contract a month shy of his 32nd birthday feeling mild disappointment at having made $90 million instead of $120 million or even $150 million; and even then, he’ll still have a few years of high-level performance left with which to barter on the free agent market. In a worst-case scenario, his children will still grow up rich.