When they had gotten the case about some stolen antiquities he'd suggested that he go under cover. He'd thought that he'd have to argue, but Gibbs had surprised him when he'd agreed before Tony had finished giving his opening arguments. He'd been gearing up for a fight, only to realise that Gibbs had agreed. He'd taken a moment to bask in the warmth that washed over him again when he realised that Gibbs still trusted his opinions and suggestions.
This operation had been set up with his input being key, he'd made up the back story, and they'd all worked to get it set up quickly. With all the precautions that they had taken, and with the team as well as Abby and Ducky behind him he was confident that they would succeed.
But things had been against them from the start, they hadn't had all the information that they needed, their suspect had proved to be more dangerous than they had reason to suspect, and the chase had lead them further than they thought it would. They had been prepared for something to happen to the tracker that Tony had on him, had almost expected it really, what with Tony's ability to track trouble to him and all.
But the thing that he hadn't counted on was the fact that he could relate to Jeffrey, that even though he was playing a character, he was acting, and trying to get information out of Jeffrey he was fast coming to like the guy. He hadn't been ready for the final showdown that he had had with Jeffrey, he'd wanted to give the guy a way out, but it wasn't to be. It had come down to either himself or Jeffrey walking away alive, and at the time even he hadn't been sure which way it would go.
Gibbs had turned up seconds after he'd had to shoot Jeffrey, he hadn't been able to make himself move when Gibbs had approached them, hadn't even been able to look up when Gibbs had opened the door. He had felt hollow, empty. He hadn't been able to take his eyes off of the gun that rest in his lap until Gibbs had gently removed it, then helped him out of the car. He'd watched as Gibbs had gotten the investigation of the scene under way and as Ducky had looked him over first, then he watched as Gibbs almost seemed to hover close by. Which he'd been grateful for when he'd taken a nose dive into the pavement. Gibbs had caught him and eased him down onto the ground, he heard Ducky and Gibbs talking with the EMT's arguing over whether he should be taken to hospital, but they had won and instead Tony had won a trip to Gibbs place to sleep and be looked after for a couple of days.
It had been strange at first, sure he'd been to Gibbs place before, but never under these circumstances. He'd never had someone to look after him, make sure that he was all right. He knew that Ducky had followed them back to Gibbs place and had checked him over again, and that they had agreed that all he needed was some rest and good food, and an ear to listen if/when he needed to talk. He'd struggled with it for a time, only giving in when he realised that he really wasn't in any shape to take himself home or look after himself. When the nightmare had come Gibbs had been there, reassuring him, soothing him, and urging him to talk about it. They'd sat up for the rest of the night just talking about what had happened. How Tony had come to think of Jeffrey as a friend, and the fact that he'd ended up having to kill his friend.
It was during this time that he realised just how much he had come to care for Gibbs. The only other person he had ever wanted to impress, who's opinion he had sought had been his father, but it wasn't a father figure that he saw in Gibbs, it was more. And that scared the hell out of him.