In the second round of the 1996 Draft, the players that were drafted before the Colorado Rockies picked were outfielder Jacque Jones, outfielder Milton Bradley, and shortstop Jimmy Rollins, who was, by far, the best of three. The Philadelphia Phillies drafted Rollins with the 46th overall pick of the draft.
Rollins was drafted out of high school in the San Francisco Bay Area and he was in the majors by 2000. He spent parts of 17 years in the majors, which was highlighted by three All-Star Game selections, four Gold Glove Awards, and winning the 2007 NL MVP award.
Rollins currently is the Baseball Hall of Fame ballot for the first time this winter.
Throughout most of Rockies history, the Rockies have had decent shortstops. Walt Weiss, Troy Tulowitzki, and Trevor Story are the three best and, in fact, the latter two have been the Rockies only two Opening Day shortstops since 2007. But with Rollins, he could have helped the Rockies through their lean years of shortstop.
From 2001 (Rollins’ rookie year) up until 2007, the Rockies had five Opening Day starters at the position and none were particularly great. They included Neifi Perez (2001), Juan Uribe (2002), José Hernández (2003), Royce Clayton (2004), Clint Barmes (2005-2006).
He would have overlapped with Tulowitzki in his later years, requiring a position change for one of them but it’s something to ponder about what could have been.
In reality, the Rockies took a right-handed pitcher in the second round by the name of John Nicholson. Nicholson was traded along with Westbrook to Montreal for Mike Lansing so, in theory, it was a bit of an overpay for Lansing but Nicholson never made it above Advanced-A ball, last pitching in 1999.