When Mandel wasn't collecting balls and demonstrating strokes, he played with people whose partners were late or failed to show up. Sometimes he hit balls with older guys who played on the Evanston Township High School team. He saved his small earnings and used them to buy a new Jack Kramer model Wilson racquet, a few white Lacoste shirts, tan-coloured Fred Perry shorts. 

Mandel began to develop a wider repertoire of shots, hit a harder second serve without too often double-faulting, developed a stronger backhand. Each night he took the El back to Chicago, a fine brown clay dust on his Jack Purcells. Daydreaming, he imagined himself brilliantly winning the fifth and deciding match of the Davis Cup for the United States or playing on Centre Court at Wimbledon. He must also have been undergoing a sexual awakening at this time, but now, in his memory at least, thoughts of tennis crowded out all others. 

That same summer Mandel began to play in local tournaments, in the public parks as well as at tennis clubs in Oak Park and River Forest. He didn't have much success. He might win a round or two, but even players less good than he — who had less stylish strokes, less of a feel for the game — often defeated him. Mandel was too enraptured in his own fantasy of style. He wanted above all to be an elegant player; his opponents were content merely to win. 

That summer, too, Jerry Mandel first saw Danny Montoya, of whom of course he had heard; with fewer sports on offer in those days, Chicago papers covered prep and other junior sports more thoroughly than now. When he first saw Danny — in a tournament from which he, Mandel, had been eliminated in the first round at the River Forest Tennis Club — he recognised the game he himself longed to have. Danny had the style Mandel dreamed of, though in Danny's case style didn't keep him from winning. Danny won this particular tournament, beating a kid named Esteban Reyes who had come all the way up from Mexico 8-6 in the third set. He met Reyes at the net, shook his hand cordially, flashed his brilliant smile and walked over to his father, a small pudgy man who looked a lot like the Danny Montoya Mandel had met 15 or so minutes before at Home Depot. 

Mandel played on his high-school tennis team, which was no big deal, for tennis in the public schools of Chicago in those years was strictly a minor sport, at most an afterthought, like fencing or speed skating. The good junior tennis players were at New Trier or Evanston Township or from the western suburb of Hinsdale, where Claire Reissen, the father of Marty Reissen, who was later nationally ranked and would play Davis Cup, was the coach. Mandel played number four singles his sophomore year, and most of the kids he played from other schools — Roosevelt, Sullivan, Fenger on the far southside — wore black gym shoes and gym shorts with their boxer underwear sticking out at the bottom; black socks were not uncommon. All this was a long way from Centre Court at Wimbledon. 

Senn High School had a tennis coach who worked summers as the pro at the River Forest Tennis Club, a tall, white-haired, pink-faced, taciturn man named Major Singleton, known to everyone as Maj. Rumours had it that he had been a young flying ace in the First World War. (Mandel's friend Barry Grolnik, in later years trying to describe him to a group of people who didn't go to Senn, said, "You have to imagine a gentile John Wayne.") The coach's own tennis past was a bit unclear, though everyone who played tennis in the middle-west seemed to know Maj Singleton. One afternoon, decades later, Mandel heard Tony Trabert, on television, remarking that Stephen Singleton, in the umpire's chair, was the son of Major Singleton, "one of the great gentlemen in the game."