Note: To be clear, I've seen the first four of these on the show; the last four I made up.
Eight photos that adorn Jack Donaghy's office:
1) Liddy Donaghy.
Of course, Jack would give the place of pride to his beautiful little girl. It always got wonderful comments from visitors to his office. He had to update the photo every three months or so, as her appearance kept changing. But she was always adorable.
There was only one recurring occasion when he felt the impulse to move Liddy to a less conspicuous place. Lemon would be lingering in his office during a lull in conversation. He might be on the phone or signing some papers for Jonathan, and he'd catch her staring at the photo, a certain pained look in her eyes that he understood all too well. When that look appeared, he always tried to reboot the conversation. She'd always cover by making a remark about how gorgeous the photo was, as if she was merely admiring its composition or Liddy's beauty; but Jack knew better. It reminded him of his broken promise, of the way he'd utterly failed to help his friend in the way she most wanted and needed.
Liddy's picture also reminded Jack of...
2) Avery Jessup-Donaghy.
Jack still missed Avery terribly. She was not only his love, and the mother of his child, but also a good friend, a soul mate that shared his interests. Their work schedules limited the time they spent together, but they had never run out of things to do.
What was difficult was the lack of closure. If she had died, it would be simple, if painful, to properly mourn her. But instead, she was taken away from him bit by bit, as the reality of her situation slowly dawned on him. He'd scour the Korean news reports he had translated for him, and each week find out some other factoid that showed she was slowly adjusting to her new, captive but privileged life in North Korea. He lost his wife in slow motion, as if to a terminal disease, but without even the simple comfort of seeing her as she left his life.
In any case, Jack loved the photo, taken at some sort of formal function. Avery was stunning in the black dress, with two straps crossing on her chest and looping around her neck, her hair up to expose the sensual curve of her neck. God, he missed her, the way she touched him, the way she knew what he would say before he said it.
He thought about moving it away from his desk, so that visitors wouldn't give him the pitying looks he hated so much. It made him feel powerless and small. But he couldn't bear to hide her like that.
3) George W. Bush.
It was always a plus to have yourself in a photo advising the President of the United States. In this photo, Jack is facing the camera as President Bush looks to the side, apparently taking his advice on something. Jack always told people he was telling President Bush to go forward to with the surge in Iraq, which would usually get impressed murmurs of approval from his guests, at least the ones that weren't in the entertainment industry.
In fact, this photo, from his tenure in the Department of Homeland Security, captured a bit of Jack's unsolicited advice to not bail out Lehman Brothers. This decision helped precipitate a freefall in the economy that led to Comrade Obama being swept into office.
It was probably the worst piece of advice Jack ever gave anyone.
4) Kim Jong Il.
It was odd that this photo, him shaking hands with the "Dear Leader" himself, had sat in his office so long, given all that had happened since.
But he remembered that day in 2005 like it was yesterday. The Winnipeg Iron Works, subsidiary of NBC, was entering a joint venture with Pyongyang to form the Ahp Chanagi Party Meats company, and Jack was in Beijing running the negotiations. It was one of the finest maneuvers of his business career, requiring great skill to work his way around various trade and export restrictions with the hermit kingdom. Yoking it to a Canadian subsidiary had been his idea.
Shortly after the Tracy Jordan Meat Machine fiasco, GE decided to shut down Ahp Chanagi, essentially double-crossing the North Koreans. Jack didn't think Kim Jong-Il ever forgave him, and figured that may have played a role in Avery's kidnapping several years later. He kept the photo around because it reminded him of the dangers of hubris.
5) Don Geiss.
When he remodeled his office after his first year at NBC, he reluctantly took the decorator's advice to move his large painting of Geiss to his home. However, he had to have some reminder of the man who had been his father figure for most of his adult life. Unlike most of the photos on his desk, this was an offical photo, with Mr. Geiss in a dignified pose, looking seriously at the camera.
He missed Don Geiss too.
6) Milton Greene.
It was a nice quirk of fate - or if Jack was honest, a nice quirk of Liz Lemon - that his real father would enter his life just before Don Geiss left it. He took the photo that first week that he met Milton. They stood together in his office as Jonathan snapped a photo, just as Jack did with the other contest winners. But this one was of long-term interest to Jack.
He talked with Milton on the phone fairly often, certainly more than with Colleen. Jack was pretty sure that Milton was the second nurturing relationship that he'd ever had in his life.
In his weaker moments, Jack wonders what he would be like if Milton had always been there. If he'd be a better man than he is today.
7) Colleen Donaghy.
Jack didn't really want to have this photo in his office, with Colleen flashing a rare, phony smile for the camera. After he'd had Jonathan take the snapshot, she'd gone right back to berating him about impregnating Avery.
But Kabletown was a family company, and when Hank showed up it was always useful to show how beloved his mother was.
8) Liz Lemon.
If having a photo of Kim Jong Il was odd, having one of Liz Lemon was both pointless and counterproductive. Pointless, because if he was in his office to view the photo, he would certainly see her in no more than a few hours, no matter the time of day; counterproductive, because it led to questions. Questions from Kabletown people who didn't understand, questions from his other subordinates, questions from dates that inevitably ended up in his office for one reason or another.
The last was no longer a problem, as he hadn't yet summoned the strength to date again. If nothing else, Liddy absorbed much of the time and energy he might use for such pursuits.
Furthermore, when he decided to find a photo of Liz the summer after Avery left, he'd had trouble finding a suitable one. Neither Lemon nor Jack were the type to generate a long photographic record when they socialized. He had some pictures of them dressed up at various black tie events, but none of those seemed to capture what he was looking for. He eventually settled on an (unused) TGS production photo an NBC photographer had taken for the show's website. He wasn't sure exactly when it was taken; he guessed a couple of years ago.
The print was black and white. Jack and Liz were standing at the podium in the studio during a taping of her show. Her attention was fixed on the stage, hair up, her bespectacled face showing pure contentment. It must have been a sketch she wrote, because she always got that look when she got to see her words turned into performance, at least if it was going well.
In her concentration, she was also unaware that to her left, Jack was watching her, taking in her joy and reflecting it his own face.
Jack kept this photo in an inconspicuous place because he didn't want Lemon to notice it, wonder why it was there at all and trip all over herself with awkwardness. But the reason it was there was simple. Among all the photos that reminded him of lost love, death, and regret, this was the only one that always made him smile.
END