Stevens stresses he does not regret joining Carlton in that year's pre-season draft after a proposed trade to Collingwood fell through.
But the two-time Michael Tuck medallist admits he sometimes ponders what might have been had he not left Alberton Oval at 23 after 127 games in six seasons, one year before the Power's maiden premiership.
"It's one of those things you'd love to have a crystal ball because at the end of the day everyone wants to play and win Grand Finals because that's what football is about," Stevens says.
"If I had my time again I might have stayed at Port because they were a great club and I went back to Carlton and had years of rebuilding at that stage.
"The chance is, I might have been the game's record-holder because I played a lot of footy at Port and would have played a lot of games there by the time I finished.
"Who knows what type of success I could have had over there?"
Stevens was one of four former players AFL.com.au spoke to recently who grappled with the same career-defining decision Hawthorn superstar Lance Franklin faces at the end of this year - re-sign with your original club or seek a fresh start elsewhere.
Along with Stevens, former Essendon champion Paul Salmon decided he needed a new home, at Hawthorn, while Stevens' former Power teammate Warren Tredrea and Richmond icon Matthew Richardson remained one-club players.
Although Franklin will make his decision as a restricted free agent, he's almost certainly grappling with many of the same issues Stevens, Salmon, Tredrea and Richardson faced before free agency's introduction.
Stevens told AFL.com.au making the decision to leave Port was tough.
Stevens was in contract discussions with the Power throughout 2003 and thought he would re-sign when he had coffee with his coach Mark Williams just days before Port's preliminary final loss to Collingwood.
After that defeat, Stevens sensed the Power's playing group might have missed its chance at a premiership after winning the 2002-03 minor premierships but bowing out in consecutive preliminary finals. The opportunity to join a team building towards premiership success appealed, he says.
Unlike Franklin, whose family relocated from Western Australia to Melbourne shortly after he was drafted by Hawthorn in 2004, Stevens was separated from his Melbourne-based family while at Port.
And Stevens says the pull of home ultimately swayed him to leave.
"At the time we were obviously a good side, but I pretty much made the decision based on my family. I wanted to return home to Melbourne," Stevens says.
"I always wanted to return home at some stage and I think at 23 I needed to go then. Otherwise I was going to sign a four-year deal at Port and stay there for the rest of my career.
"If I was an Adelaide boy, there wouldn't have been an issue, I would never have left Port Adelaide."
After joining Carlton via pick No.2 in the 2004 pre-season draft, Stevens would play 104 games for Carlton before a neck injury forced him to retire at 29.
The hard-running midfielder reached the same individual heights at Carlton as he had at Port, matching his second-place finish in the Power's 2000 best and fairest award with runner-up finishes in Carlton's 2004-05 best and fairest counts.
But Stevens would play in just one final at Carlton, the Blues' 2009 elimination final loss to the Brisbane Lions, after playing in nine at the Power.
Tredrea also came close to missing the Power's 2004 premiership.
Port's only premiership captain told AFL.com.au he asked the Power for a trade at the end of the 1998 season when, as a 19-year-old key forward, he didn't think he was getting enough senior opportunities under coach John Cahill.
Port refused his request but even after Mark Williams took over as Power coach the following season Tredrea seriously considered offers from three or four clubs during 1999, with Collingwood and the Sydney Swans his most ardent suitors.
Tredrea, who came out of contract at the end of 1999, said Collingwood's offer was the most tempting because he'd long thought he'd only leave his native South Australia to play for a big-name Victorian club.
With the Magpies languishing near the bottom of the ladder that season, Tredrea knew there was a strong chance he'd be able to get to Collingwood through the pre-season draft rather than having to rely on Port agreeing to a trade. (The Pies ultimately finished wooden-spooners and selected out-of-contract Brisbane Lion Shane O'Bree with the No. 1 pick in that year's pre-season draft.)
However, after pondering the Magpies' offer for about six weeks, Tredrea decided to stay at Alberton Oval. Ironically, like Stevens, family played a big part in his decision.
"At the end of the day I thought I'm an Adelaide boy, I'm probably not going to earn the absolute market rate I would have if I'd moved, but I was getting well compensated for a player who'd played 35-40 games," Tredrea says.
"And Port had always looked after me, so I had no reason to leave from a professional point of view.
"It was just whether I wanted to move to Melbourne and continue my career there, and the best decision I ever made was to hang around.
"At the end of the day I made a decision based on career opportunities in terms of football. From day one that 'Choco' (Williams) came in as coach he told me centre half-forward was mine to lose and he really backed me in.
"And in terms of post-football career opportunities SA was always a better option for me."
Now a football commentator and on-air host for Triple M in Adelaide, Tredrea hosted 20 listeners at a Collingwood-Carlton clash at the MCG last year and admits he wondered that day what it would have been like to play in front of crowds of 70,000-plus most weeks.
But Tredrea, who holds the Power's records for most games (255) and best and fairests (four), cherishes being a one-club player.
"When you win and succeed at your one club you're actually signed for life and I'm privileged to be a life member of Port Adelaide," Tredrea says.
"You've got that ownership with your club and with your fans – you've given your whole career to one place – and you've always got a football home to go to and be part of."
Salmon, however, feels "blessed" to be a two-club player.
After joining Essendon as a 15-year-old, Salmon crossed to Hawthorn 15 years later at the end of the 1995 season.
At that time the 205cm forward/ruckman was already one of the Bombers' all-time greats. He had played 209 games, been a key player in the 1985 and 1993 premierships and led the Bombers' goalkicking in seven of his 13 senior seasons.
However, Salmon describes his decision to leave Essendon as "one of the easiest I've ever made".
Salmon had unsuccessfully requested a trade at the end of 1994, but a season later he and Essendon agreed his time at Windy Hill was up.
After several injury-plagued seasons Salmon decided he could either retire or try to reinvigorate his career at a new club.
He says the opportunity to see what he was capable of playing in his "best position", the ruck, rather than rotating between there and attack as he had at Essendon, influenced his decision to play on.
Salmon also received offers from Geelong and Richmond, but after initially leaning towards the Cats was swayed by a concerted pitch from the Hawks.
"I was blessed to end up with the Hawks. It was a perfect fit because although they had Steve Lawrence in the ruck he needed support," Salmon says.
"The Hawks showed a lot of faith in me and I was just totally reinvigorated. It reinforced to me just how much your mental state can dictate your form.
"Although I was very proud of what Simon [Madden] and I achieved as a ruck/forward combination at Essendon, it was time to spread the wings a little bit and see what I could do as a ruckman."
Salmon played 100 games for Hawthorn from 1996-2000 and had such a profound impact in those five seasons he was selected in the Hawks' team of the century on the interchange bench.
Salmon has no regrets he didn't finish a one-club player.
"I think it's a wonderful sentiment for a player to want to finish a one-club player," Salmon says.
"I could have retired at 31 as a 200-game player and been a one-club player. But what purpose would that have served if I'd missed out on five years playing at Hawthorn and achieving what I'd achieved there?
"I feel blessed as a footballer to play for two clubs like Essendon and Hawthorn."
Ironically, though, Salmon regrets his decision to come out of retirement in 2002 to re-join Essendon, saying at the time it caused "a level of detachment" from Hawthorn.
Franklin enjoys an exalted status at Hawthorn few players have matched, but Richmond favourite son Richardson was similarly revered at Punt Road during his 17-season career.
Unlike Franklin, Richardson was tied to Richmond from birth. His father, Alan or "Bull" as he was widely known, played 103 games for the Tigers from 1959-69, including the 1967 premiership.
Richardson might have grown up in Devonport, Tasmania, but he was a passionate Richmond supporter.
Richardson says that connection was so strong he never seriously considered breaking it.
Not when Fremantle made a serious play for him in 1999, nor when Carlton followed suit in the mid-2000s. Not even in an era when the Tigers struggled so much that just three of Richardson's 282 games from 1993-2009 were finals.
"I never really got to the point of looking at offers and contracts from other teams to be honest," Richardson says.
"I was always a Richmond supporter, my dad played there and I guess that side of it outweighed ever wanting to move anywhere.
"Now that I've been retired for three or four years, I'm happy to look back and have played my whole career at one club.
"I obviously would have liked to have played more finals, but there's no point dwelling on what didn't happen.
"I always had the feeling that I wouldn't be able to live with myself if I left Richmond and then they had success and played finals – that was always my overriding emotion."
As for Franklin, Richardson says he is well within his rights to put contract talks with Hawthorn on hold until the end of the season, as he signalled he would do last month.
However, Richardson says Franklin should now stick to that timetable and not bow to public pressure to reopen talks during the season.
"You can't really be having a bit each way during the season, which I think may happen at times," Richardson says.
Similarly, Stevens, Salmon and Tredrea don't have any problems with Franklin's decision.
Stevens says his year-long negotiations with the Power in 2003 did not affect his form or create tension with his teammates.
Tredrea says as Port captain, he would talk to players who were in protracted contract negotiations with the club, but not in an attempt to influence their decision.
"From a leadership point of view you'd want to have a chat to him and say, 'Is there anything we can do to help you or make things easier?'" Tredrea says.
"You can't go up to him and say 'you should do this, this and this', because realistically you've been through the same thing as well.
"You're not going to try and change the outcome of it because realistically this is a guy running his own business."
Tredrea does not think Franklin's restricted free agency status will influence his decision.
Although it means Franklin can get to the club of his choice more easily than Tredrea could in 1998, Tredrea thinks players still only move if they are unhappy or "chasing the buck".
Tredrea senses Franklin is neither unhappy at Hawthorn, nor motivated by money over team success.
Richardson also points out that marquee players like Franklin rarely leave their original clubs.
However, Stevens says it's hard to predict what Franklin will do without knowing his individual circumstances.
He has some simple advice for the Hawk.
"I'd just say to him, 'Assess what you want to get out of the second half of your career and where you want to play footy'," Stevens says.
"And if that's based around his family or going home to play in Perth where he grew up watching footy, make that decision.
"Because it's a hard call and you can only do what you want to do."
Nick Bowen is a reporter with AFL.com.au. Follow him on Twitter: @AFL_Nick