In the spring of 1997 the Yankees organization was feeling pretty good and confident about itself. After a decade and a half of high hopes followed by major disappointments, the team was fresh off a World Series championship and cruising to a 96-win season. Their confidence was riding so high that in that year's amateur player draft they selected a player seemingly because his last name was familiar and not because he was a good baseball player. Move over Midas, whatever the Yankees touched was now going to turn to gold.
Except it didn't. In the 54th round they selected a 21-year old outfielder out of Washington University in St. Louis named Russ Chambliss. The scouting report was most likely two words long: Chris' kid. Chris Chambliss was a longtime major league first baseman who made his hay as a Yankee in the late 70's, belting one of the most famous home runs in franchise history, and was now serving as the team's hitting coach. Either this pick was a favor to Chris, or nostalgia got the best of the Yankees because if they hadn't drafted him, nobody else would have. The younger Chambliss kicked around the Yankees' system for a couple years but never reached higher than class A-ball. He was also clearly overmatched by minor league pitching as he had a combined .115/.174/.128 slash line from 1997 to 1998. He was done with professional baseball by 2000.
The Yankees thought they were on to something, though, and undauntedly pushed their new late-draft strategy. With their 47th round pick of the 1998 draft they chose Jeff Nettles, a 19-year old third baseman. Of course, Jeff is the son of Graig Nettles, arguably the greatest third baseman to ever don the pinstripes. Jeff wasn't quite the disaster that Russ Chambliss was but he underwhelmed at each level and the closest he got to the big leagues was a few cups of coffee at Triple-A Columbus. Two years later, and again in the 47th round, the Yankees drafted Jeff's older brother Tim, a 23-year old outfielder out of the University of North Carolina. Tim played only 52 games during his two years as a Yankee minor leaguer before calling it quits.
After three swings and misses, the Yankees decided to up the ante in 2003. In the 42nd round they selected an 18-year old first baseman named Taylor Mattingly and three rounds later took Andre Randolph, a 22-year-old second baseman. If those names and positions sound familiar, it's because Taylor and Andre are the offspring of Don Mattingly and Willie Randolph, respectively. Those two men held down the right side of the infield for the Yankees throughout the majority of the 80's and Randolph was serving as the team's third base coach at the time while Mattingly was on the verge of being named the team's hitting coach. The picks were symbolic, poetic and heart-warming, but also terrible baseball decisions. Taylor played 24 unimpressive games for the Tampa Yankees in 2003 and never played professional baseball again. Andre was even less impressive in 11 games for the Staten Island Yankees that year and was done professionally by 2004.
The team seemed to come to their senses when Brian Cashman was given more control over personnel decisions in the middle of the 2000's. For a few years the bottom of their draft board didn't look like a long lost lineup card. However, recent drafts have proven that the Yankees may be in the middle of a nepotism renaissance. When their 42nd pick of the 2010 draft came along they selected high school outfielder Michael O'Neill, you may know him better as Paul O'Neill's nephew. Michael chose not to sign with the team in favor of playing baseball at the University of Michigan, but the Yankees would not be denied. In the 2013 draft they took Michael again with their 3rd round pick and this time he stuck around. While he still has plenty of time to get on the right rack, so far Michael is slashing .223/.292/.327 over his two seasons in Low-A Charleston.
The Yankees weren't done handing out favors though. In the 26th round of the 2013 draft they selected a high school pitcher named Cal Quantrill. Apparently as reparations for Joe Torre abusing the right arm of his father, Paul Quantrill, during the 2004 and 2005 seasons. Eleven rounds later the Yankees chose another high school pitcher named Joshua Pettitte. It just so happens that this was the same day that Joshua's dad, legendary Yankee pitcher Andy Pettitte, was busy recording his 250th career win for the team. Alas, both Cal and Joshua decided to attend college rather than sign with the Yankees, but there's always next time.
All of these picks are great personal stories for everyone involved. There's probably no greater joy for a big league baseball player than seeing his son get drafted by a team that he played for. Sometimes a pick like this can even result in a team striking gold, just ask Tommy Lasorda and Mike Piazza. However, once the feel-good narrative wears off, the organization is more often than not left with a useless player that they just wasted a draft pick on. In their current state, the Yankees are not an organization that can afford to do this. By most accounts their farm system ranks in the bottom third of the MLB, which is bad news considering how old and injury prone the big league roster is. It would be in their best interest to draft players, even in the later rounds, based on things like scouting reports, analysis and actual results rather than their family tree.
Nevertheless, while you're tracking the twilight of the 2014 draft today, be sure to put on some Sly in the background. You'll probably see a real-life story that will make you all warm and fuzzy inside. At least for a little while.
The historical draft information in this article was taken from The Baseball Cube.