Phil Oates Named Massachusetts Assistant Principal of the Year

Why yes, I did thieve this graphic hence the crazy. Original at

Now, I know what you’re thinking…there have only been FOUR days in 2023 but Phil Oates, Weston Middle School Assistant Principal, is so impressive that they already called it for him. Yes, the Massachusetts School Administrators’ Association announced today that Phil Oates, Assistant Principal of Weston Middle School, has been selected as this year’s Assistant Principal of the Year.

Now before we get into the official blah-blah, it behooves (be-talons?) this Owl to say that I am a major fan of Mr. Oates. Not only for his excellent combination of compassion and discipline which made the Owlets’ sixth grade and seventh grade (first half until pandemic) the best middle school experience anywhere and yeah, sorry Saxe Middle School in New Canaan, I know of what I speak–but for making the pandemic-affected eighth grade as positive as possible (with the amazing Principal Gibbons, of course). Wow, that was a long sentence but fortunately, Phil is a mathy person NOT an Englishy person.

If you have had no contact with Mr. Oates, you may want to catch some of his best-ever moments on the Wes-TEN in a fashion throwdown with Principal Peri of Weston High School on the Wes-TEN. Pandemic days, made that much better with laughter. Hey, Sarah Lappi and Alton Jenkins, where are you now? No poutine jokes please.

Wes-TEN #24: “Who Wore It Best?”

Now for the officialese, blatantly lifted from the Weston School Committee facebook page. Who says plagiarism lives? Me.

Phil Oates has served as Assistant Principal at Weston Middle School for the past six years. He graduated from Tufts University with a bachelor’s degree in mathematics. He also earned a master’s degree in secondary math education from the University of Massachusetts and a master’s degree in organizational management from Endicott University. Phil’s career in public education spans middle to high school.

Prior to serving as WMS assistant principal, Phil was an interim principal for a year at J.R. Lowell Elementary in Watertown. He was a Title 1 math tutor, taught math and coached football for nine years at Watertown Middle School. Additionally, Philip taught for two years at Cambridge High School Extension Program.

Phil was nominated by WMS Principal John Gibbons, who in his nomination wrote, “Phil has had an incredible impact on shaping our school’s culture. He fosters well-being and safety for all students and adults in our community. He leads with an abundance of positivity, which he brings to every interaction with every individual in our organization. Phil is a dynamo who has a unique engine providing him with a tremendous amount of energy, enthusiasm, humor, and caring.”

Congratulations to Phil for this outstanding recognition of his leadership. And for always, always, being willing to start the laughter.

And go ‘cats!

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