When’s the best time to trade Logan Webb?

“Never!” should be your answer.

No good San Francisco Giants fan would ever dream of trading the team’s ace. That’s Buster Posey’s job, and if he’s going to be any good as a President of Baseball Operations going forward, he ought to start popping ashwagandha pills before bed.

Yesterday, Andrew Baggarly wrote an article for The Athletic reiterating certain parameters for the offseason that owner Greg Johnson had previously mentioned to Susan Slusser in a Q&A for the Chronicle, John Shea in the Standard, and Tim Kawakami on his podcast, mainly that the team has very little interest in signing a starting pitcher to a long-term, nine-figure deal:

According to club sources, because of a number of financial considerations, the Giants do not anticipate making the nine-figure investment required to sign Imai — or any of the other top pitchers on the free-agent market.

Line that up with the other reporting and you see a really clear redline for the front office imposed by ownership:

[JOHN SHEA’S INTERVIEW] Asked if the Giants could sign a pitcher for $100 million or more this offseason, Johnson said, “I’d say we’re going to be very cautious about those kinds of signings.”

[SLUSSER Q&A] We’re in need of one, possibly two [starting pitchers]. […] As Buster has said, I think we’re hesitant about any pitcher on long-term deals when we have a young core sitting there. So it’s a question of what is available in the marketplace and what we can do on a shorter term basis.

[TIM KAWAKAMI PODCAST, 26:30] We can go up, but I think the risk is long-term deals, having too many people on similar six-year type deals that create less flexibility with the payroll […] you’ve gotta be careful about too many of your players being late thirties at a high payroll level. […] I would say we’re gonna be very cautious about those kind of signings [paying 100 million+ to a starting pitcher].

Sure, this ownership line is about free agency and the current major league payroll, but Logan Webb will be a free agent after the 2028 season. He’ll be entering his age-32 season, with (theoretically) 1,600-1,650 innings on his arm. Dylan Cease (who will be 30 in 2026, admittedly), just signed a 7-year, $210 million deal ($30 million AAV). Just given that basic projection and the broad market profile for a top of the rotation-type starter — neverminding inflation, which could push that into the $220-$230 million range — Logan Webb should not figure into the team’s plans.

Unless he’d be willing to sign a 3-year, $99,999,999 million deal? I use that term because 4 years would put him just barely above what he’ll be making at the end of his current extension ($24 million in 2028). Now, maybe if the owners win and get a salary cap, this all becomes a bit moot, but even in that half-imagined scenario, it stands to reason that Webb’s time as a Giant is closer to its end than its heyday if only because of the economics.

The Giants don’t want to spend money on old starting pitching, so they won’t. By their terms, Logan Webb will be an old starting pitcher by the end of his current deal. Can they do better than taking the draft pick that comes from tagging him with the Qualifying Offer and letting him walk? After all, the Qualifying Offer might go away in the next CBA.

Then it comes down to competion. Does the team want to signal to their fans that they’re giving up by trading their ace? Well, for the purposes of this exercise, let’s assume that the Giants are what they’ve been for most of the last 10 years: mediocre to bad. If Tony can’t reVitello-ize the franchise and they’re hanging around .500 come August or September, what then? Back at this year’s trade deadline, Posey made the tough choice to trade away talent in hopes of reloading for a run down the line. It’s a similar situation in the “trade Logan Webb” scenario. Again, you should not want the Giants to trade Logan Webb, but there’s a very real baseball argument to be made that it’s the right move if the Giants keep being the Giants.

So given all that the best time to trade Logan Webb is after the 2026 season, provided the Giants are still a .500 at best team. While a potential lockout could affect his value, that’s two full seasons for the receiving team, sort of like the situation the Padres were in when they acquired the aforementioned Dylan Cease. In exchange for Cease, San Diego gave up their #5 overall prospect (MLB Pipeline’s #85 overall prospect) along with their #7 and #8 prosepct and a reliever. In trying to imagine what the Giants could do to make up for losing Logan Webb, the differences are key, of course:

• San Diego got Cease for his age 28 & 29 seasons, while any team trading for Webb would get 30 & 31.

• The potential downsides would have a higher probability because of the age: injury risk up, stuff down. Mitigating that — on paper, anyway — is that Webb is not the same pitcher as Cease though both have (knock on wood) stayed healthy; but, as a sinkerballer, I would say that Webb’s decline tail would be longer than a pitcher like Cease’s, even after turning 30.

• Webb will make $47 million total over the final two years of his deal ($23MM in 27, $24MM in 28). Cease cost just $21.75 million over his two years ($8MM in 24, $13.75MM in 25 through arbitration).

Those are the negatives. The positives are this:

• Webb has been the second-most valuable starting pitcher in MLB (19.1 fWAR) since the start of 2022, and leads the sport in innings pitched (820).

• Webb has received Cy Young votes in each of the past four seasons, been named an NL All-Star twice, and added a Gold Glove to his trophy case this season (Cease has never been an All-Star and received Cy Votes just twice).

• His home run suppression and groundball rates are simply elite and tough to replicate. If he were to hit the free agent market after 2026 instead of the trade market, he’d cost quite a bit more.

So, it’s a little difficult to find a 1:1 comp. Looking at some other trades that might suggest a shape of a deal:

• The Orioles gave up INF Joey Ortiz (#8 prospect, #63 on Pipeline’s Top 100), LHP DL Hall, and a Competitive Balance Round A pick for one year of Corbin Burnes (then 29) two offseasons ago.

• The Rangers got the #4, #17, and #27 prospects in the Dodgers’ system at the 2017 trade deadline in exchange for Yu Darvish (age 30).

• In 2014, the Rays traded away David Price at the deadline for Willy Adames, Drew Smyly, and Nick Franklin (Seattle’s #4 prospect)

A team’s top 10 prospect who is in the top 50 of MLB prospects would be one of the players involved, and it’s not impossible that younger, pre-arb or arbitration players could find their way into a deal, either. The Giants’ potentially great minor league talent — if it actually pans out — is still 2-3 years away from reaching those upper minors, and so adding players who are already at that threshold or have stepped through it makes a lot of sense to fill the donut hole in the organizational depth. And, since these would be players coming from a non-Giants organization, the chance of them actually being good is much higher (again, because of the Giants’ historical failings in player development).

Of course, making plans with starting pitchers is a foolish endeavor, but Logan Webb’s performance and track record has made it so tempting — so easy! — to do over the past few years. It’s foolish to take him for granted, and that’s why I think doing the boring ol’ SABR thing of “extracting maximum value from a player” might actually be to the Giants’ benefit here — again, if the Vitellossaince doesn’t happen in Year One.

It’s still hard to fathom a wealthy enterprise like the San Francisco Giants dumping one of their best players in order to maintain payroll flexibility and add players to their talent pool their mostly (and historically) barren farm system has failed to produce, but it’s also a headscratcher that the Barry Zito deal and/or the Jeff Samardzija deal still give ownership hives. It’s tought to argue against those being what’s underpinning the firm’s plans. Sure, there’s plenty of statistical/actuarial evidence to support why long-term contracts to free agent pitchers are a bad idea, so, I can see why that motivates Greg Johnson and Buster Posey to shake their heads and tsk-tsk anyone asking otherwise; but, that just makes it clearer — to me, anyway — that Logan Webb’s likeliest and best contribution to the future of the franchise might be as The Ultimate Trade Chit.