They selected him with the 24th overall pick in 2008, and took another high-ceiling prep outfielder in Zach Collier at No. 34.
"This is why you scout," Wolever said the day he drafted Hewitt and Collier. "These are the kind of players we grew up liking and wanting in the organization. Because when these guys hit - and not all of them do - you're not talking about an average major-league player. You're talking about a well-above-average player. And to me, that's what you win championships with."
Hewitt, six years later, is a bench player at double-A Reading with a lifetime minor-league batting average of .225 and 748 strikeouts in 2,137 at bats. Collier hovers around .200 at Reading, where he was assigned for a second straight season.
Maybe, then, the lesson is that drafting baseball players is hard. It is the most inefficient process of the four major sports, and even tougher when teams attempt to project the rawest talent. Last week, the Phillies issued public claims of a new strategy. Disclaimer: It could be a smokescreen because the team has engaged in such tactics prior to previous drafts.
Former general manager Pat Gillick preached the value of drafting high-ceiling, athletic high school players. He was not the only believer. It was a tenable plan for a franchise awash in young talent at the major-league level such as the Phillies in the mid-2000s.
Those circumstances have changed.
"If you were a first baseman or a second baseman or a shortstop or catcher, guess what, you weren't going to play here for a while," said Wolever, now an assistant general manager. "And when you pick down low, sometimes your interest changes a little because you have a chance to take a little bit safer pick on a chance if it hits with a high ceiling, it's going to be a high-impact player."
It could be that the Phillies adapted too late, or that they did not invest enough money into the amateur draft before Major League Baseball enacted a hard cap on bonuses. They dreamed on Larry Greene, Shane Watson, and Mitch Gueller with three first-round picks in 2011 and 2012. All three are hurt; Greene looked like a bust even before a wrist injury.
They chose high school shortstop J.P. Crawford with the 16th overall pick last June. He was not their prototypical high-ceiling pick. Crawford's best tool was his bat, which has played well beyond anyone's best expectations through one full year of professional baseball.
The strength of this year's draft, Wolever said, is college pitching. The Phillies have chosen one college pitcher with their first pick since 1994. That was Joe Savery in 2007.
"I think baseball's mind-set has changed," Wolever said. "You look around, I think baseball players with great makeup and maybe not as much ability sometimes have a way of getting there and being better than you ever anticipated them being.
"If you look back at our drafts . . . we've tried to have a balance here where we've incorporated baseball players, but also picked high-ceiling guys."
The Phillies are the only National League team whose first-round picks since 2004 (including compensatory ones) have produced negative wins above replacement in the major leagues, according to an Inquirer draft analysis. They have picked low and surrendered numerous picks for free-agent signings.
Their 12 picks were the fewest of any NL team; nine teams boasted at least 16 picks during that span. Their average draft slot was 30.5. Both Atlanta (29.4) and St. Louis (32.3) occupied a similar spot.
In 2008, after the Phillies took Hewitt 24th and Collier 34th, they drafted another high-ceiling outfielder named Anthony Gose with the 51st pick. Gose was used as a trade chip for Roy Oswalt, and finally emerged for Toronto in May.
He is one possible success story from the Phillies' strategy.
"All people talk about is those first-round picks," Wolever said. "Well, the draft for me is a hell of a lot deeper than that. We've had very good luck behind that."
Luck is relative in a 40-round process that champions futility. A team is "lucky" to produce two or three decent major-league players from one June draft. More often than not, the stories are wistful, like that one day when Anthony Hewitt made everything appear possible.
Inside the Phillies:
The No. 7 overall pick has produced significant talent since the turn of the century. Nine of 14 selections have reached the majors.
2000 COL RHP Matt Harrington
2001 BAL LHP Chris Smith
2002 MIL 1B Prince Fielder
2003 BAL OF Nick Markakis
2004 CIN RHP Homer Bailey
2005 COL SS Troy Tulowitzki
2006 LAD LHP Clayton Kershaw
2007 MIL 1B Matt LaPorta
2008 CIN 1B Yonder Alonso
2009 ATL LHP Mike Minor
2010 NYM RHP Matt Harvey
2011 ARI RHP Archie Bradley
2012 SD LHP Max Fried
2013 BOS LHP Trey Ball