Other Bears greats like Dick Butkus and Dan Hampton followed closely behind, but Singletary was the first of the legends to make the grand entrance. By design, Brian Urlacher was the last, sprinting out of the tunnel and onto the field.
It was one of many times history intersected with progress Monday night, the Bears' intended theme for the special occasion. This was supposed to be a celebration of Bears old and new, a night when the Bears found some strength out of the old colonnades standing firmly around their 21st Century stadium, an opportunity for the franchise to find some direction in its tradition.
Turned out the Bears do not yet have a present worthy of their past.
"A huge game [and] we just embarrassed ourselves one more time," Urlacher said after the Bears' 38-23 loss to the Packers. "We went out there and laid a big one."
For the third straight game, the Bears looked unprepared early and overmatched often. They didn't stop the run, didn't protect the passer and didn't play like a team that had worked on correcting its problems over the past two weeks.
The gap between the Bears and their opponents so far this season has created more than a sense of urgency in the Bears' locker room; it has spawned a sense of concern for the job of coach Dick Jauron.
Asked if he worries about Jauron's future, Urlacher said, "If we play like we do [against the Packers], we do. Our coaches get us ready to play, and that's all they can do."
Only Anthony Thomas' resurgence in the fourth quarter prevented Bears fans from going home without feeling good about something. The running back gained 110 yards on 13 carries but didn't get a handoff until the second quarter.
"Anybody in my position wants the ball, but obviously it wasn't in the game plan," Thomas said as he trudged off the field. "I wasn't trying to prove a point, I was trying to win the game."
With 12:36 left, Thomas gave the Bears their best chance to do just that. He showed a burst that hadn't been obvious since his rookie year and sprinted 67 yards for a touchdown. The longest run of Thomas' career made it 24-16, and suddenly the fans were waving orange pompons again.
But seven plays later, it went eerily quiet again. The Packers marched down the field, giving the impression that whenever they wanted to move the ball, they could. Whether it was Ahman Green breaking loose for a 32-yard run or Brett Favre capping the drive with a 9-yard touchdown pass to Javon Walker, the Bears lacked answers.
"We just didn't make playsthat's our season," Urlacher said.
While many wondered whether workers would complete construction on the $611 million structure in time for Monday night's game, nobody thought the Bears still would have so much work left to do when the stadium finally opened.
A little more than three minutes into the game, the Packers exploited a weakness against the run that the Bears spent the past two weeks shoring up. Green, the man every Bear identified as the player to stop, scored on a 60-yard touchdown run around the left side that took the crowd out of the game.
Bears cornerback Jerry Azumah missed a tackle that sprung Green, who broke into the secondary so quickly strong safety Mike Green couldn't get an angle. Before people had settled into their seats, it was 7-0 Packers.
Shortly after that, a bad start got worse.
With 1:05 left in the first quarter, the Packers' Marcus Wilkins zipped through the center of the Bears' line untouched and blocked Brad Maynard's punt at the Bears' 29. Bhawoh Jue recovered for Green Bay at the 20 and the Packers needed only two plays to make it 17-0. A Favre pass to tight end Bubba Franks went for 14 and Green scampered for the remaining 6 with 24 seconds left in the first quarter.
As the first quarter ended, Bears fans unleashed 20 months' worth of frustration with a chorus of boos.
Many of them were directed at Stewart. A bad interception at the beginning of the third quarter by Green Bay's Na'il Diggs took the Bears out of a drive that had eaten up five minutes and represented the type of poor decision-making that fuels Stewart's critics.
Stewart's best plays came on the ground and he gained 71 yards on 12 carries, including an irrelevant 1-yard touchdown dive with 1:28 left. He completed 25-of-44 passes for 201 yards and two interceptions.
But despite the cries that will come for Stewart to be replaced, so much more remains wrong with the Bears than just their quarterback. Wide receiver David Terrell had a holding penalty that negated a 60-yard Thomas touchdown run. Cornerback R.W. McQuarters had a defensive holding penalty that kept a Green Bay drive alive. The list goes on and on.
Where do the Bears go from here? Only four teams that started 0-3 ever have qualified for the playoffs.
As the Bears filed slowly off the field after the loss, a man held a homemade sign that summed up the feelings of many in the crowd of 58,933: "Build a team, not a stadium."