1: If a union strikes when it has too much leverage, there's a risk there as well at overplaying the hand. If the Times does just fine during the election, then the union helps make the case their members are overrated. If the Times crashes and burns during the election, they might make the value of the contract weaker.
2: In an election where trust and reliability of independent media are really being called into question, something like this could have outsized negative impact. There's potentially a lot of damage to innocent third parties, including smaller syndication partners.
Does SWE striking even mean anything to a company? If factory workers don't show up, no products are made. If a SWE doesn't show up, the website is just fine (see elon buys twitter).
SWE impact is measured in quarters or years, especially at a big company that doesn't have public deadlines for project delivery.
If you don’t have a fire department and your house catches on fire, it is an obvious demonstration of their value. Likewise, if NYT goes down tomorrow or they don’t have content to drive traffic, it shows management they can’t mess around. The best case scenario for management is a dip in traffic but no major issues.
Also, it takes two to tango. For any of the negative outcomes you mention, NYT management is equally to blame. Why is it the union’s responsibility to acquiesce to whatever terms to maintain trust and reliability?
2: In an election where trust and reliability of independent media are really being called into question, something like this could have outsized negative impact. There's potentially a lot of damage to innocent third parties, including smaller syndication partners.