The man, according to Wainwright, would ask how he was doing, and Wainwright would give him a dollar or spare change. In the midst of the Blue Demons' 0-18 Big East season, the homeless man delivered the low blow.
"I'm about five steps by him, and he says, 'Hey Coach, your post players really suck,'" Wainwright said. "I had heard about it in the paper and in the arena, but here was a guy on a busy street corner who is obviously down in his luck, and he's telling me my guys suck. That's when I knew we still had relevance. But I was never embarrassed. We have to be better on the court, better at finishing games."
DePaul is in the news this week because of the tectonic shift within Wainwright's staff. The orders came from within the athletics department that changes had to be made. Gone are associate head coach Gary DeCesare and assistant Ramon Williams, who were dismissed a month after Scott Wainwright, the head coach's son, also resigned.
For a few days, the elder Wainwright was the only coach on staff.
On Tuesday, though, he hired former Kentucky and Illinois assistant Tracy Webster, a native of Harvey, Ill., and a former guard at nearby Wisconsin. (He also was an assistant at Ball State and Purdue.) Webster could be a recruiting changer for Wainwright as he attempts to create a presence in the city.
The staff shuffle comes the same week that the early-entry deadline for the NBA draft passed with two DePaul players on the list. That's right -- DePaul had two players entering the draft, and the Blue Demons didn't win a regular-season Big East game. Dar Tucker is expected to stay in the draft. Wainwright said Tucker had said he didn't have an agent but that he would. Sophomore Mac Koshwal declared, but the 6-10 center is apparently going to see where he could land before making a decision on staying in the draft.
Tucker, a sophomore, led the Blue Demons in points at 18.5 a game, while Koshwal was third on the team in scoring (12.2 ppg) and tops in rebounding (9.6).
This is the second time in three seasons the Blue Demons have lost their top scorer to the draft. Wilson Chandler left early in 2007.
"When I look back, I wasn't prepared for Chandler to come out two years early," Wainwright said. "Had he stayed one more year, it would have given us more stability. He might have been the preseason player of the year had he stayed. But we didn't have a backup. Tucker and Koshwal had to play more as freshmen."
Wainwright is hopeful that he can absorb the loss(es) better this season with the arrival of Chicago-area JC guard Mike Stovall and redshirt sophomore Eric Wallace, who was a bench player at Ohio State as a freshman.
"I made a strategic mistake in that we were too young," Wainwright said. "I should have tried to get a JC guard. We still have only one senior. We are saturated with young players. I believe they're Big East players, but they wouldn't be playing right away [on other teams]. We were a wonderful 30-minute team last season."
Losing Tucker means the Blue Demons will likely be picked to finish last in the Big East next season, even in a league that is going through an overhaul.
And despite Wainwright's optimism, he's also a realist and said he knows DePaul basketball isn't exactly the talk of Chicago right now. The Second City is a pro town, and with the Bulls in the playoffs, the Blackhawks going through a rebirth, baseball as popular as ever, and the Bears being a 24/7 addiction, the Blue Demons aren't doing enough to make themselves relevant -- even if a homeless man close to DePaul recognizes the deficiencies.
"You need to give people a reason to come," said Wainwright of his program, which plays near O'Hare Airport at the Allstate Arena, nearly an hour from campus if traffic is bad.
"If you look at schools in our league that play in municipal facilities, like Georgetown, it's winning that drives them there," Wainwright said. "We don't have what schools like West Virginia and Notre Dame have with their on-campus arenas."
The Demons didn't quit this past season, beating Cincinnati in the Big East tournament in New York. There were a few competitive contests against Notre Dame (by 10) and Marquette (by nine), but the most frustrating thing for Wainwright and the fans was the difference in play when DePaul went against the lower-echelon teams.
"We played our worst against South Florida, St. John's and Rutgers," Wainwright said. "That's the definition of maturity. We didn't understand the urgency the same way we did against Pitt or Villanova."
Webster comes to the staff at a crucial time. Wainwright is about to enter his fifth season at DePaul and has four years remaining on his contract. Wainwright took Richmond to one NCAA tournament and UNC Wilmington to two. He didn't suddenly forget how to coach when he came home to Chicago. Yet, the numbers don't lie. Wainwright has had one winning season in his first four at DePaul and has yet to make the NCAA tournament.
"We have to have a significant signing in the 2011 class, and within our area there are some tremendous young players," Wainwright said. "In today's times, people have to believe in you from your area. That can build momentum in your program. We're on target academically and the players are graduating. But we have to make a significant jump in recruiting. We need the younger players to say they want to go to DePaul."
The recruiting clearly hasn't been awful, with one NBA player in Chandler and possibly two more in Tucker and Koshwal.
"We have to upgrade the talent, since this league is an incredible grinder," Wainwright said. "We have to have more stars, since ours have a tendency to leave early."