On Wednesday, January 11, outgoing U.S. President Barack Obama delivered an emotional farewell speech in Chicago that was watched live, on TV and on live stream, all over the world.

On that same morning in Singapore, his longtime friend Kirk Wagar was hustling between farewell meetings and appointments lined up back to back — his time, after all, is limited to the same window Obama has: as a political appointee, his term ends together with Obama's, and in an unprecedented move, President-elect Trump's administration transition team is not giving him or any of the existing ambassadors in other countries additional time for handover.

The decision to stay behind in Singapore instead of flying to Chicago earlier to be with his friends, and of course the one at the podium, was a tough but resolute one Wagar had to make. He simply had too many people he needed to meet and say goodbye to -- there just wasn't enough time for him to take off for home early.

In this final week he has here, Wagar is hastily packing, making arrangements and putting on a brave smile for the press and public as once again, he, his wife Crystal and two of their three young children (their oldest has been living in Miami) prepare to uproot themselves and their lives here.

We certainly couldn't blame him for asking us for five minutes to step outside his residence, where we met him that afternoon for our interview, for a smoke — that day was, after all, surely a tough one for him emotionally, just like November 9 last year: the day the world realised American voters had decided, in a rather painfully decisive manner, to send shockwaves around it.

That day, for the 47-year-old, would have been a nightmare playing out in real time that he couldn't wake up from: state after state was falling from Blue to Red, even by CNN tallies, not just by Fox. The Florida race must have been the toughest to watch -- back in 2008, Wagar played a pivotal role in clinching the populous state's precious 29 electoral votes for Obama (he chaired the finance committee for his election efforts in Florida), and on election night, it was head-to-head with a less-than-one-point lead on Trump's part as soon as numbers started coming in.

Despite all that, and with the certainty of crushing Democrat losses looming over his head, Wagar put up a brave face to address the Singaporean media with his take on the then-possible outcome:

But whatever his emotional and psychological state may be by this point, come January 20, the United States of America will have a new President. All eyes are on President Donald J Trump and his incoming administration as they chart a new course in domestic governance and international relations.

And it can't be denied: there is a palpable sense of uncertainty and resignation around the world as an, ahem, colourful POTUS takes to the Oval Office.

Despite this, Wagar says resolutely, just as he did two months ago, that we have nothing to fear (because, quoting President Franklin Roosevelt, "the only thing we have to fear is...fear itself").

"I appreciate the amount of interest that the world has in who America has currently in the head of our government. But I remind people every chance I get... long before the election happened, is that, we engage in so many different ways: through our culture, through our educational institutions, through businesses that provide jobs and do technology transfers. So we are more than one party, one person."

Kiasu but not kiasi

Dressed in a blue checkered suit with his signature brightly-coloured socks, Wagar righted himself to his usual funky and jovial self in time to sit down with us for a short half-hour chat, alternating between serious and light-hearted topics with ease and self-assuredness.

There is something to be said about a man who could have dedicated his limited media slots to only the biggest newspaper and broadcaster, but instead chose to give one of them to a website that doesn't even call itself a news portal (he also gave us an interview before, by the way).

That's simply reflective of his character, though -- Wagar, who started out as a decidedly undiplomatic first-time diplomat, was passionate -- even kiasu — about engaging as many Singaporean groups as he could throughout his time here. He attended as many cultural events as he could, tried as many types of local food as he could, even scolding his friends for not taking him to more coffee shops to eat hawker food.

He reveals to us that Singapore has of course had a great impact on his family, in particular his children -- his three-year-old daughter Rhys, whom he begrudgingly enrolled in school at the age of one and a half (see, kiasu), now speaks Chinese, for instance -- and he says he is now "100 per cent Miami and Singaporean", as opposed to previously being "100 per cent Miami" only.

And it is with this drive-to-win certainty that he also asserts that the U.S. will remain engaged in our region despite the winds of change, given the growing importance of Asia and America's long-standing presence in the Pacific. There are 37,000 American companies based here in Singapore, after all, with many U.S. business and intellectual leaders who are extremely familiar with Southeast Asia.

"Elections have consequences and this administration will have different priorities than President Obama’s administration. But I think when it comes to international affairs, global engagement and particularly, engagement in Asia, I think you can count on more of the same."

The last ambassador to meet LKY, S R Nathan

There is a certain poignancy that accompanies his reflection on his time here, too — himself originally a Canadian, Wagar travelled to the U.S. when he was 18 to study, and ended up sinking roots there, setting up his own law firm before he met his wife, who also had her own practice. Both of them gave up their firms as a consequence of relocating to Singapore when Wagar was appointed to the position on September 4, 2013.

His story, interestingly, reflects the cosmopolitan melting pot of the U.S., and meaningfully, Singapore's, he tells us.

I think that the most important thing that my wife Crystal and I have learnt in this job is that the richness of Singapore is its neighbourhoods, and its folks from all different background, all different economic spheres, all different jobs, educational levels; that’s the tapestry that make Singapore special. Crystal and I are from Miami. And one of the reasons that we love Miami is because it’s a confluence of cultures that infuse: the food, the fashion, the art and just the dinner conversation. And Singapore has so many similarities to Miami in that regard, it’s just different cultures and so we’ve learnt a lot.

The meaningfulness of Wagar's term was not lost on him either — he and his family were here to witness some key moments in our recent history: the passing of founding Prime Minister Lee Kuan Yew and former President S R Nathan, for instance, meant he was the last U.S. ambassador to meet and interact with them.

He was also here for our 50th birthday celebration, as well as our last General Election, and was a key wingman in setting up his buddy Obama's 12th State Dinner for PM Lee Hsien Loong and his wife at the White House, even though he downplays his role in it.

"I could tell story after story about the things we’ve gained, the people we’ve met, the things we’ve learnt. You know, being here for the celebration of life of Lee Kuan Yew, it was incredible to be here for that. And see how the country mourned the celebrated. Being here for the election and 50th year celebration, was fascinating to watch... Particularly poignant for me to be at the funeral for President Nathan. He was exceptionally kind to (my wife) Crystal and myself. The former Singaporean ambassador to the United States was very giving of his time and just one of the nicest people I’ve ever met. So it’s with a lot of humility that I realise I’m the last U.S. ambassador that’s going to have spent time with Lee Kuan Yew, the last U.S. ambassador that spent time with President Nathan. And that’s something that I’ll cherish."

If it helps, Wagar knows he'll be back often, even with his family, to maintain the relationships they've forged and also to see the people he hasn't had the time to say goodbye to before leaving.

In fact, he tells us he will already be back in March for a planned meeting.

3 things the Ambassador won't forget about Singapore

As Ambassador Wagar looked back with fond memories of his time here, he recounted some of his less official experiences among his highlights, such as eating at our food centres.

1. Chope-ing seats with tissue

The “chope-ing” is one of the strangest things I’ve ever seen in my life, but it’s incredible manners that people (have). It just wouldn’t work in the U.S. I’d put a tissue there, we don’t care.

2. The taste of durian

"I’m glad I did it, how about that? It’s impossible to say that you’re going to try to understand the Singaporean mindset and be at dinner parties where arguments are all about which durian dealer is legit versus those that aren’t without trying. So I had to try. But, you should be safe to know that I will not be taking a lot of your personal stock back to send back to my home."

3. "Kiasu but not Kiasi"

"I was always competitive. I think that... I don’t take losses as personally and I am not afraid of failure as much as, you know, maybe some others. But I like to win.

(So you are kiasu la, but you are not kiasi?) I think that’s right. I think that’s exactly right."

We leave you with a meaningful and timely bit from Ambassador Wagar on what he took away from his posting in Singapore:

Top photo by Juan Ezwan

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