His most significant achievement in doubles was making the finals in the 2009 U.S. Men's Clay Court Championships, losing to the Bryan brothers.

[8] Levine, along with Dudi Sela, Shahar Pe'er, Sharon Fichman, and Camila Giorgi is one of a number of young Jewish tennis players who are highly ranked.

[13] He and his family moved to Florida in the US when he was 13 years old, because his younger brother Daniel suffers from ulcerative colitis and the year-round warm weather was much better for him.

In 2004 he won the Eddie Herr International Boys 18s doubles championship with Michael Shabaz, an Iranian-born Assyrian-American.

At the 2005 USTA Junior Nationals, where he lost in the singles semifinals and doubles finals, both 7–6 in the third set, he was judged to have the best service return.

[23] He won the 2005 Wimbledon boys' doubles championship along with Michael Shabaz over Samuel Groth of Australia and Andrew Kennaugh of Great Britain.

[34][35] On May 23, 2007, Levine lost his first college match, in the quarterfinals in the NCAA Men's Singles to Washington's Alex Slovic.

[34][38] Levine and Ouellette were defeated in the quarterfinals of the 2007 NCAA Men's Doubles championships by the eventual winners, Middle Tennessee State's Marco Born and Andreas Siljestrom.

In November 2007, Levine won his first pro title, the $75,000 Music City Challenger in Nashville, Tennessee, along the way beating world # 109 Robert Kendrick of the US, 7–5, 6–4, # 148 Sam Warburg of the US, 4–6, 6–3, 6–3, and # 170 Dušan Vemić of Serbia, 6–2, 7–5.

[51] In late December Levine won a wild card berth into the main draw of the Australian Open.

He trained and played sets with Max Mirnyi, Xavier Malisse, Andy Murray, and Tommy Haas.

He also won the Türk Telecom İzmir Cup challenger tournament in doubles in Turkey, with partner Kei Nishikori of Japan.

[2] In October Federer again invited Levine to join him for an extended practice session in Dubai, as preparation for the Australian Open.

Levine ... is seven inches (178 mm) shorter and 45 pounds lighter than Safin, but when it counted ... the American was faster and stronger.

"[67] When Levine clinched the win he looked up and pointed into the sky in acknowledgement of his grandmother Lillian Kimmel, who had died three years prior.

[69] For the first set and a half of their match, Levine (described by The Sunday Times as having "the pugnacity of Jimmy Connors and the fashion sense of Eminem") looked as though it was he who was the top 20 player, as he hit low forehands and approached and dominated the net, but in the end Wawrinka prevailed, 7–5, 5–7, 3–6, 3–6, despite Levine saving 17 of 23 break points in the match.

[73][74][75][76] Levine next played in the Hall of Fame Tennis Championships in Newport, Rhode Island, making it as far as the quarterfinals, and along the way upsetting sixth-seeded world # 48 German Philipp Petzschner, 7–6(7–3), 6–2.

[78] In doubles Levine partnered Israeli Dudi Sela, and defeated Denis Istomin of Uzbekistan and Josselin Ouanna of France 6–4, 6–4 to make it to the quarterfinals.

[79] Entering the 2009 US Open via wild card, he won his first round match in straight sets over Russian Teymuraz Gabashvili 7–5, 6–1, 6–2.

In September, Levine reached back-to-back Futures finals in Canada, winning in Toronto 6–1, 6–0 over Rhyne Williams, but losing in Markham to Peter Polansky.

Levine reached the second round of the French Open in June, his first Grand Slam main draw win in almost three years.

[91] Levine applied to the International Tennis Federation in late 2012 to represent Canada in future Davis Cup play.

He made it to the quarterfinals, after wins over local player Daniel King-Turner and Brian Baker, before losing to Sam Querrey.

[96] At Wimbledon, he made it to the second round with a five-set victory over Guido Pella in his opening match, before losing to world No.

[98] Beginning in the spring of 2013 during grass court season, Levine began suffering from an elbow problem and numbness in his pinky finger.

[99] By July 2014 he was back to hitting on practice courts, and though his elbow was troubling him when serving he trained during the summer with Andy Murray.

[99] However, when he attempted to come back in October after not playing competitively for 11 months, the problem recurred and was re-aggravated during a match in Houston.

[106] "He's got a great heart", said Larry Stefanki, who coached Andy Roddick and has previously worked with John McEnroe, Marcelo Ríos, Fernando González and Tim Henman.

[108] He is also good friends with Canadian NHL ice hockey centre Jason Spezza and a big fan of the Ottawa Senators and Miami Dolphins.

[citation needed] On April 28, 2014 Jesse was made an honorary brother of the Alpha Epsilon Pi fraternity.