Alex Guptill was acquired by the Senators on July 1st, 2014 as a piece in the trade for Jason Spezza. The Senators also received Nicholas Paul and Alex Chiasson (both of whom may or may not be higher on this list) and a second-round pick, while the Senators also gave up Ludwig Karlsson to the Dallas Stars.
Guptill was a third-round pick (77th overall) of the Dallas Stars in the 2010 Entry Draft. Guptill was drafted after playing two years of Junior A hockey. In 2010-11, Guptill played with the Waterloo Black Hawks of the United States Hockey League (USHL), notching 25 points in 43 games, a disappointing total, though the team overall was well below average. He then played three years at the University of Michigan, which played in the Central Collegiate Hockey Association (CCHA) as part of NCAA Division I hockey. He notched 33 points in 41 games in his freshman season, being named CCHA Rookie of the Year. He followed that up with 36 points in 38 games in his sophomore season, leading Michigan in scoring. In 2013-14, he seemed to take a step back, scoring 25 points in 31 games. Following that season, he signed a two-year entry-level contract with the Stars, joining the Texas Stars on an amateur tryout contract for the end of their 2013-14 season. This means that he will forgo his senior season at Michigan to play professionally with the Binghamton Senators in 2014-15.
Though Guptill is undoubtedly talented, his career thus far has been marred by discipline issues. He was charged with public urination in August 2011. In his sophomore season, he was left home from a road trip due to his "effort and attitude". He was suspended at the start of his junior season for being charged with assault and battery, charges which were later dropped to a single assault charge for misdemeanour. He was a healthy scratch for a game last season because his coach was unimpressed with his defensive effort in previous games.
It is quite possible that the discipline issues are simply a case of being young. Turning pro may help him to outgrow these problems, being surrounded by older and more experienced hockey players, as well as no longer being the among the most talented players on his team. He has the size, shot, and net presence to be a solid forward, and his skating poses no issues. A couple years of training under Coach Luke Richardson may put him on the path to becoming an impressive NHL presence.