For starters, he might take you on a searching lead that starts in St Kilda's forward pocket and ends near your team's forward 50m line.
Gasping for air, you think you've got him where you want him when the Saints kick to another option.
But, before you know it, he's escaped your clutches and is hightailing it back towards the Saints' forward line.
You lag behind, tongue hanging out, as the St Kilda skipper runs on, knowing only a teammate or a Saints error can stop him.
But, even if fate smiles on you, you soon realise there will be no respite.
Just like the Road Runner, Riewoldt will keep running, to the next contest. It will be that way for the rest of the match.
At the end of which - no matter how quiet you may have kept him - you'll look and feel as ragged as the poor old Coyote, one of the cartoon world's longest-suffering fall guys.
It has been that way for Riewoldt's opponents since he made his AFL debut in round 15, 2001.
In that time, he has almost single-handedly redefined the role of the key forward, introducing the type of work ethic that was once the sole domain of the game's elite midfielders.
On Sunday, Riewoldt is due to play his 200th AFL game and, at 28, football's running man has shown few signs of slowing down.
In the lead-up to the Saints skipper's milestone, the AFL Record spoke with three people who know Riewoldt the player intimately, and each marvelled at the work rate that has defined his career.
Geelong centre half-back Harry Taylor said Riewoldt was the hardest-running forward he had played on. Former Collingwood full-back Simon Prestigiacomo said in his 15-season career he'd played on just two other tall forwards with a similar work rate - ex-Richmond star Matthew Richardson and Brisbane Lions skipper Jonathan Brown.
Former St Kilda full-back Max Hudghton, who played alongside Riewoldt for nine seasons, was more blunt, describing his ex-teammate as an "animal … with an insatiable appetite to run".
Taylor, who was last year's All-Australian centre half-back, said Riewoldt was so hard to keep up with because he had the full arsenal of running weapons - speed off the mark, a "cruising" speed of more than 24km/h achieved through a textbook, efficient running style, and lung-busting endurance.
Taylor also offered an insight into what it was like to follow Riewoldt on one of his long out-and-back leads down the ground.
"Once you get back to the (St Kilda) goalsquare, you think, ‘He's just done 200m worth of leading, surely that's enough'," Taylor said.
"But he'll still find some energy to go back at the ball if it's in another spot. That's what separates him from a lot of the other players I've played on.
"It's not necessarily that first or second effort - because most of the good players can do that - it's those third and fourth efforts he produces.
"He just has that ability to keep pushing himself to the limit, no matter what."
One game against St Kilda, in particular, remains scorched in Taylor's mind. It was the epic round 14 clash of 2009 at Etihad Stadium. Both the Saints and Cats entered that game undefeated, St Kilda ultimately emerging a six-point winner in a thrilling preview to that year's Grand Final.
But that's not why Taylor remembers it. He can't forget it because it was the day Riewoldt introduced him to a level of fatigue he had never known before.
"The majority of the game I was just absolutely exhausted from the amount of running he did," Taylor said.
"It was the most he's ever run in a game when I've played on him. The roof was closed, it was a really quick game and he was just up and down the ground continuously.
"He never stopped and I can remember thinking after that game, ‘Wow, that was definitely the hardest I've had to run in a game of footy'.
"I just felt like I was always chasing him. I never felt like I had some ascendancy and he had to follow me."
Prestigiacomo recounted similar experiences of playing on Riewoldt. For him, a particularly long Riewoldt out-and-back lead in round one of last year's NAB Cup soon came to mind.
"We went pretty much from inside the St Kilda 50m to our forward 50m line. He then managed to slip past me and he sprinted just as hard all the way back.
"I think both of our tongues were hanging out and Nick said, ‘That was a fair run wasn't it? I almost ripped my hammy'."
But Prestigiacomo said keeping up with Riewoldt when he doubled back towards goal was just the start of your problems.
"He could take those marks running back with the flight of the ball, or crumb if the ball hit the ground," he said. "He just didn't stop."
Riewoldt had a killer instinct too, Prestigiacomo said. Knowing he had an aerobic advantage over his opponents, he would often try to ram it home near the end of quarters when they were longing for a break, he said.
So how do you try to combat such an aerobic animal?
Taylor said after playing on Riewoldt the first time, he had focused on trying to match the Saint's endurance.
But he conceded that alone was not enough, saying most clubs now rotated two key defenders on and off the Saints skipper.
Even then, Riewoldt's opponents remain highly reliant on the pressure their teammates put on St Kilda players up the field, Taylor said.
"If your teammates can pressure the incoming kick, it gives you a better chance," he said.
"Having the other 17 guys helping me is the only reason I've had some success on him in the past."
Prestigiacomo said in recent seasons Collingwood had also assigned two defenders to Riewoldt, but in a zone-based tag-team. For example, Prestigiacomo might have manned Riewoldt when he was inside the Saints' forward 50m, but Nick Maxwell would take over when he worked further up the ground.
Another tactic Prestigiacomo had employed with some success was putting body blocks on Riewoldt.
"You really had to use that sort of bodying. If he wanted to run, it meant he had to run around you or go through you," he said.
"If he got in front of you, he knew he was fitter than most people so he would just run and run and wouldn't stop. You couldn't let him get that metre on you because he'd increase it to five metres and so on.
"When he pushed up the ground, you had to bump him to try to stop him from getting back and getting goal-side on you because, once he did that, you were in a fair bit of strife."
As a former teammate, Hudghton observed Riewoldt's single-minded and fastidious preparation for matches and said his elite running ability stemmed directly from it.
"The way he prepared, his appetite for hard work just became part of the way he played - it was second-nature to him," Hudghton said.
"Whether it was pre-season or mid-year training, Nick had an insatiable appetite to run and train hard. I always say the best trainers become the best players and Nick is a classic exampleof that."
Hudghton said Riewoldt's commitment extended to his unique pre-match routine, in which he takes to the ground long before anyone else to do a series of run-throughs, visualising what he wants to do in the match.
Hudghton admitted he was lucky to be able to observe Riewoldt from the opposite end of the ground and marvel at his running, rather than having to try and keep up with him.
"He's certainly torn some very highly-rated players to pieces over the years," Hudghton said.
Playing on him is a daunting challenge but it's one Taylor has relished.
"It's something I really look forward to," he said.
"It's something I know I'll be able to cherish when I retire. When I'm sitting around with family and friends, I'll be able to say, ‘I used to play on this guy called Nick Riewoldt, who was just an absolute superstar'.
"It gives me a lot of pride I've been able to do that."
When a highly respected peer says that about you, it speaks volumes about your contribution to the game. Clearly, Riewoldt's contribution has already been substantial.
NICK RIEWOLDT
Born: October 17, 1982
Recruited from: Southport (Qld)
Debut: Round 15, 2001 v Adelaide
Height: 193cm Weight: 96kg
Games: 199 Goals: 441
Player honours: best and fairest 2002, 2004, 2006, 2007, 2009; All-Australian 2004, 2006, 2008, 2009 (capt); AFLPA MVP 2004; leading goalkicker 2008, 2009; NAB AFL Rising Star 2002; pre-season premierships 2004, 2008
Brownlow Medal: career votes 95
