Yet he's not happy.
Firstly because of the gaps in his CV - no World Cup or European Championship experience with Republic of Ireland - and also because he feels United should have done more under his watch.
In particular, the sight of Chelsea stealing the Premier League off them last season still rankles, which is why O'Shea views Sunday's clash with Liverpool as a must-win game, especially in light of United's sloppy start to the 2010/11 season.
O'Shea said: "Hopefully, there are a lot more medals to come for me. As a player, you remember the defeats a lot more than what you win. That is what drives you on. I should be sitting here with a lot more FA Cup medals, for example.
"And when you don't win the league, the intensity to reclaim your crown can be all-consuming.
"So after Chelsea getting the better of us last year, we are going all out to win the title back. But there are factors against us - Arsenal, Liverpool, City, Tottenham, Villa and Everton - being six of them.
"All across the Premier League, squads are improving year after year and so many teams are capable of taking points off us.
"Take Everton. Never mind what they did to us last week. Last season, they finished really strongly and if they had have had a stronger start and fewer injuries, they would have finished in the top four.
"The competition is fierce. Liverpool today will be a real battle. But I actually love these games. I love the pressure."
It is just as well. Otherwise, there is no way O'Shea would have survived for over a decade at Old Trafford, averaging 40 games a year.
No way Mr Versatile would have stayed on the payroll while so many other big names - Roy Keane, Ruud van Nistelrooy, Gabriel Heinze, Gerard Pique, Phil Neville and Nicky Butt - left because Sir Alex Ferguson realised their time was up.
While that tells you everything you need to know about O'Shea's ability, it also gives you an insight into his temperament because if he was mentally weak, Fergie would have handed him his P45 long ago.
O'Shea said: "Being at United, being in big games where you NEED to win, those are the situations you should enjoy rather than be afraid of.
"I want to be playing in front of full houses, walking out into a packed Old Trafford. We're fortunate in that respect that even when we play away from home, it's a full house and you can feed off that atmosphere in every game.
"I wouldn't have as much mental strength if it wasn't for the manager. His little team-talks and chats with you, before a certain game or at the start of the season, are crucial to building your self-belief.
"And then you look around at certain older players, Scholesy, Ryan, Gary Neville, and you learn from their example.
"I remember a conversation I had with Nicky Butt a couple of years ago.
"Butty said to me: 'Stay there for as long as you can because you don't know what you have until you leave it.' That struck a chord because Butty was always a great influence."
So too were a number of others along the journey - David May, Laurent Blanc, the Neville brothers and Roy Keane.
Yet the biggest motivation came from within.
He said: "In a dressing room with so many characters, you have to quickly learn to stand on your own two feet.
"You look around the club and appreciate that everything is geared towards you as an individual, getting you to peak and keeping you at your peak for as long as possible. The success you get from that, such as winning trophies, can only make you feel good."
Yet so does another personal accolade.
A year ago, O'Shea passed the 350 appearance mark at United, something he is incredibly proud of, not just because of the competition he faces for a starting slot, but also because of where he came from.
As a kid, he was no Wayne Rooney or Ronaldo, cocksure he would have a future in the game.
Instead he was a gangly, one-footed, laid-back guy who was accused of lacking passion.
How his critics have learned to eat those words.
O'Shea said: "When you play for a club like this, you look around at certain individuals and the same thing comes back to you. Desire is the key factor determining our success.
"All the big men have it here, the boss obviously, but also Roy, the Nevilles, Ryan, Scholesy, Ruud, Cristiano. Everyone.
"I have it too. Remember the season I came through (2002/03)? I had to take the chance because there aren't too many of those available at United.
"I proved I could put a marker down and get a run in the team. And we ended up winning the league that first year. I always look back on that as being the key for my whole career."
Now, times have changed.
For starters, he's older and rather than simply look forward, he has something to reflect upon.
Yet, despite being 29, he scans the grey beards in his company and feels he can survive at the top for another decade.
O'Shea said: "A few years ago, the club brought in SportsLab, which AC Milan have been using for years - a reason why their players survive in the game so long.
"There are different factors to it, you do a medical screening at the start of the season when everything is checked and they might come to you after two weeks of the season and identify what you need to do to improve - yoga, ball-work or whatever.
"That's helped us. I feel able to go on and on."
Damn right you haven't! Do me proud and score some goals! I wear your name on my jersey for a reason! Sheasy!!! :D
He's one lucky chap,there's many better players around but he has won the lot.He's the weakest link in the squad in actual fact.giving away possession cheaply,too slow,can't defend..reaction slow also.
but won't deny his contribution these yrs..jus that hope to see more of wes brown,he isn't performing up to standard these days.