Seriously…you’re the one in charge of admissions and you have one spot left…two otherwise equal candidates. It all comes down ro the letter.
You get a letter from a trustee saying one of his employees has a kid he’s never mret, but who he hears is a good kid.
And you get a letter from me, talking about his aptitude in math, his work in the classroom, his relationships with his peers and his teachers,his work ethic, his work in NHS.
I would be disappointed in the trustee if they were willing to give an unknown kid any notice. I would be disappointed in any school that puts weight on who you know instead of who you are. Take that school off my list.
I would thank the boss for the offer and tell him you are willing to risk going it alone. If your kid is rejected, the rec probably would not have mattered. If he ends up on the WL and it’s your son’s first choice at that time, well… you can try to have him meet the boss (even by phone) and have him write directly to him to see if he can help. At that point, the school will effectively have determined that your son is "good enough ", so the pull might help.
A trustee at a school on DS’ list offered to meet with DS and put in a word “which may or may not help” (trustee’s words) if he applied ED or wanted off their WL. But absolutely only if he would attend. We never called in this favor - DS was admitted to a few schools he liked better.
As almost everyone as said, it’s about how well the trustee knows the applicant and what the trustee says about the applicant.
A recommendation from someone who doesn’t know the applicant well is worth very little. One from a trustee who has never met the applicant is worth less. The trustee will probably give the LOR because it’s easier to do that than refuse, but the LOR is going to say very little about the applicant, which telegraphs the fact that the trustee really doesn’t care if the applicant gets in.
A kid from my offspring’s high school alma mater got into H a number of years ago. Lots of people get into H from the school, but they usually have more impressive gpas, test scores and ECs. Then it came out that her dad was best friends from childhood with a very famous H professor. Every year, they celebrated one holiday together with their families. They continued to do this after their parents had died and they themselves had married and had children. They also telephoned each other at least a couple of times a month. Sometimes, they vacationed together.
So, the professor wrote a LOR that probably said something along the lines of " I have known this applicant from infancy. I’ve watched her grow up. She’s voraciously curious. I’m discussed current events and other topics with her numerous times over the years and she’s unusually articulate and very well-read. She’s the daughter I always wanted to have. She belongs at H and it’s important to me that she be admitted."