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."