When I think of older (old school?) Boston writers who took young dudes under their wing with success, I think of SLY (actually old school, painted with lots of younger people thru-out the last 25+ yrs).
MONK.
MES, AVES (imo, the thing that made ITD so successful was that it had several generations of writers, thus various energy levels, focuses on various targets, but the whole time older guys were bringing up the young gens the right way).