After a tournament in 1984 at the age of 72 Siff, suffering from leukemia, was having a meal with friends in a restaurant when he was taken by to the hospital where the doctor advised him that he should remain hospitalized, but he refused and returned to the tournament the next day. It should also be mentioned that Siff had open heart surgery a few months earlier and his spleen had been removed shortly before this tournament.
Aided by a couple of shots of cognac he defeated then Senior Master (later IM) Elliot Winslow to win the tournament. It was this event where he scored wins over two Experts (2000-2199), two National Masters (Fritzinger and Michael Tomey), Winslow and GM Peter Biyiasas that earned him the Senior Master rating. Unfortunately his rating dropped to 2399 (one point below the SM title) before his rating was published. At the time of his death his rating stood at 2266.
The only child of Russian emigrant parents, Siff was originally from the Bronx, New York City. He received a four year scholarship to one of New York's finest private schools and joined the Empire City Chess Club in the Bronx. Arnold Denker wrote about Siff in My Best Chess Games 1929-1976 that Siff had a very enterprising style and was very original in his approach to the opening. Denker added that when it came to openings Siff was "far ahead of the times.” Denker also wrote that, probably due to the demands of work, he completely disappeared from tournament play. Denker also believed had Siff continued tournament play in a few years he “would have contributed a great deal to the theory of the openings."
Siff, who retired as a machinist in 1976, faded into obscurity after his successes in winning the championships of Boston, New England and Florida in the 1950s. Before moving to California, Siff was the 1956 Massachusetts champion and in 1958 he tied for first with John Curdo and Orest Popovych.
At the end of his life Siff, who never married, was barely eking out an existence. One reason was that for many years he gambled on card games. At the insistence of a couple of friends he eventually gave up that vice and returned to his first vice, chess.
The following game won Siff the brilliancy prize. His opponent was Dennis Fritzinger, the 1970/71 California State Champion. Fritzinger played in several Lone Pine Tournaments in the 1970s and was a contributor, along with Jude Acers, to the book Grandmaster Chess: The Book of the Louis D. Statham Lone Pine Masters-Plus Tournament 1975 by Robert E. Burger. The game is interesting because after black's seemingly innocuous 18th move a flurry of tactics followed.