From 1852 onward, Montgomery quickly rose among the ranks of Athenaeum players.(1) He was a member of the successful Philadelphia team beating New York in two correspondence games in 1855-1856.2) Montgomery was the sole Philadelphia representative in the 1st American Chess Congress (1857) in New York, beating William S Allison before succumbing to Louis Paulsen. (3) After having lost two games to Paulsen, Montgomery was summoned to Philadelphia, before he could finish the match.(1) Following the hype around Paul Morphy, the Philadelphia Chess Club was founded and Montgomery became its first President.(1) Montgomery was crucial in Phildelphia's 1.5-0.5 correspondence match victory over New York in 1859.(2) Montgomery won the 1st Philadelphia Chess Club tournament in 1860.(4) In 1861, Montgomery contested a match against New York's Theodore Lichtenhein and lost +2 -7 =1.(5) According to Reichhelm, Montgomery practically retired from serious chess after this match.(1) Montgomery played two longer contests afterwards, though, beating James A Leonard +8 -4 =2 in 1861 and losing to Gustavus Charles Reichhelm +4 -8 in 1864.(6)

After that, Montgomery resided in Philadelphia and New York and practised law for a time in the Pennsylvania region.(1) In the end, he moved to the West, where he died in Marysville, California.(1) He was stricken with paralysis first on Christmas day and then a second stroke proved fatal.(1) His play was described as brilliant, nervous and fast.(1)

(1) Gustavus Charles Reichhelm and Walter Penn Shipley, Chess in Philadelphia, 1898, pp. 25-28

(2) Gustavus Charles Reichhelm and Walter Penn Shipley, Chess in Philadelphia, 1898, p. 7

(3) Rod Edwards, http://www.edochess.ca/tournaments/...

(4) Gustavus Charles Reichhelm and Walter Penn Shipley, Chess in Philadelphia, 1898, pp. 31-32. Rod Edwards, http://www.edochess.ca/tournaments/...

(5) Rod Edwards, http://www.edochess.ca/matches/m510...