That's because the Winnipeg head coach has a different measuring stick for success. O'Shea's annual goal is winning the Grey Cup and he doesn't deem anything less as a worthy achievement.
Winnipeg finished tied for second with Edmonton last season in the West Division with a 12-6 mark. However, the season ended with a 39-32 division semifinal loss to the visiting Eskimos.
The Bombers announced Thursday they posted a $5.1-million operating profit in 2017, up $2.3 million from the previous year. They also averaged over 27,400 spectators at Investors Group Field, a six per cent boost.
"I think it's good for the organization, I think it's obviously good for the CFL,'' O'Shea said during a conference call on Thursday. "Taking pride in that personally? No, I don't put a lot of stock into that.
"They (Bombers players) understand it's an entertainment business driven by our fans but they're not thinking of that on the field. They go out and play hard for each other and because they want to win and I think that shows. That's respectful to our fans and if it turns into increased crowds and therefore increased revenue, yeah, that's a good thing.''
Winnipeg fans have been treated to winning football the last two seasons. The Bombers have a combined 23-13 record over the span and been to the playoffs both years.
But each time Winnipeg's season has ended in the West Division semifinals. In 2016 after posting an 11-7 regular-season mark, the Bombers dropped a heart-breaking 32-31 decision to the B.C. Lions.
Still, the consecutive winning seasons came after four straight losing campaigns. And from 2006-2015, Winnipeg was .500 or better just three times.
Winnipeg's resurgence has come under O'Shea, GM Kyle Walters and president/CEO Wade Miller - all Canadians and former CFL players. Walters and Miller have been in the Bombers' front office since 2013 while O'Shea was hired in December of that year.
"We kind of took the slow and steady approach,'' Walters said. "From my standpoint our locker-room and team are modelled in our head coach's mindset, which is tough, hard-working guys.
"It's encouraging when you hear guys talk around our league about what a quality organization we are now. That's what I'm most proud of from four, five years ago to now. We've won our fair share of games over the last couple of years and organizationally now we need to take it to the next step and win playoff games and a Grey Cup.''
Winnipeg won a combined 12 games in 2014-15 and O'Shea, a four-time Grey Cup champion as a player/coach with Toronto, felt the turnaround took longer than he anticipated.
"I guess there was more work to be done than I had thought and it's taken longer than I thought,'' said the Hall of Fame linebacker. "You'd like to have the situation we're in now where I think we can have a little more continuity.
"I think that would be really welcomed. From the first day until now we've gone through a fair amount of change so having continuity going forward would be really good, it would be very helpful.''
Winnipeg's rebuilding plan took off when O'Shea promoted Matt Nichols - obtained Sept. 2, 2015 from Edmonton - as the starter following a 1-4 start to the '16 campaign. Nichols led the Bombers to seven straight wins and the franchise hasn't looked back since.
The six-foot-two 220-pound native of Redding, Calif., led the CFL in completion percentage (71.0) last season. Nichols, 31, also set career bests in starts (17), pass attempts (579), completions (411), yards (4,472) and touchdowns (28) with only eight interceptions.
Nichols understands Winnipeg no longer has the element of surprise in the West Division. But he said the Bombers have the right mindset to meet that challenge head on.
"When we need a big play, guys are making them because everyone takes that ownership whereas before it just felt like people were waiting for someone else to make the play,'' Nichols said. "I think that's been a big difference for us and that comes with the type of people we have now.
"We have a lot of veteran guys who practise what we preach and when you go out there and deliver on game day it's going to trickle down to the younger guys. I think that's why we've come away with a lot of close victories the last couple of years.''
Walters was active in free agency, adding receivers Nic Demski and Adarius Bowman, running back Kienan LaFrance and quarterback Darian Durant.
But he also re-signed defensive back/linebacker Maurice Leggett, cornerback Chris Randle, linebacker Ian Wild, receiver Weston Dressler and offensive linemen Patrick Neufeld, Jermarcus Hardrick and Stanley Bryant.
"Adding Adarius was a nice piece and Nic Demski and Kienan LaFrance both bring ratio flexibility and stability,'' Walters said. "But the key was trying to keep as much of our core group as possible, which is pretty difficult in the days of one-year contracts and a hard salary cap.
"That was our focus.''
(Canadian Press/Dan Ralph)