Privately, he must be asking himself how he can justify turning down a chance of joining McLaren-Mercedes and opting instead for Jordan Mugen- Honda. Those who suggested his motivation was money rather than a quest for a second world championship maintain they have been vindicated, and Hill admits he was unimpressed with McLaren's financial proposition.
There is a belief his response was anticipated and welcomed by McLaren, all part of Formula One's political games. Whatever the substance of that theory, the reality now, on the eve of another campaign, is that Hill has palpably chosen the wrong car.
While the McLaren has been setting the pace in pre- season testing and earning the status of title favourite, the Jordan has been lagging ominously behind, sitting among midfield scavengers who will be hoping to pick up odd points here and there.
One Briton unlikely to be weeping for Hill is David Coulthard, whose position at McLaren was seemingly put in jeopardy by the team's negotiations with the former champion. Coulthard and Mika Hakkinen, who was also retained after Hill ruled himself out of the equation, have the car of the moment.
Hill concedes: "It would be unrealistic for us to think in terms of the championship at this stage. I always felt this was going to be a two-year effort, anyway. But that's not to say we won't be going into the season in a positive frame of mind."
Not, however, as positive as he and Eddie Jordan would have envisaged. The car has patently disappointed the team so far and lap times appear to confirm pit-lane predictions that Prost had the better of the deal when they exchanged their Mugen-Honda engine for Jordan's Peugeot.
Far from rejoining Michael Schumacher, Jacques Villeneuve and the others in the main event, Hill may have his hands full containing his own team- mate, Ralf Schumacher. It is reported that the younger of the German brothers has been relishing the Englishman's obvious discomfort.
The scenario is exasperatingly familiar for Hill, who hoped against hope he might lead Arrows from obscurity to prominence last season, only to depart frustrated, if a lot richer. Another pounds 4.5m would be some consolation this year and at least Jordan start further up the ladder and have the resources to improve. To a point.
The big points beckon for Coulthard, now sensing the chance to firmly establish himself as Britain's No 1 driver and mount a genuine challenge for the championship. He was adamant all last summer he was optimistic of keeping his place at McLaren and that this was the place to be. His judgement appears impeccable.
McLaren are in the ascendancy, Adrian Newey's car flying clear of the rest the moment it was released from its box. If Mercedes can achieve the reliability to match the undoubted power of their engine, and the Bridgestone tyres fulfil their promise, then the Woking package will prove irresistible.
Which would leave Coulthard to see off his generally more fancied team- mate and prove he is worthy of the championship. Still not 27, the Scot ought to have time on his side, but such is the competitive nature of this business he knows there is no guarantee of another such opportunity. A member of the team said: "I've never seen David more focused."
Coulthard concurs: "I've prepared for this season better than for any other. I've left nothing to chance. Physically and mentally I'm ready.
"I had a short break at the end of last season, then got stuck into my training and I've worked really hard on my fitness. It was good to know that every night while I was in the gym, the other drivers were sitting watching CNN.
"When you are fitter physically it helps you become stronger mentally. You are more alert, and that has been evident through the testing."
Despite the McLaren's speed in testing, however, Coulthard, like Hakkinen, insists the real gauge will be after Sunday's opening grand prix in Melbourne. Coulthard said: "The car appears to be good, but until we actually start racing we don't know anything for sure. We certainly hope to be competitive and I've been confident all along that we would have a car capable of winning races.
"At the same time we know that Williams will be strong, Ferrari will be strong and Benetton will be strong. And of course my team-mate will be very competitive."
Hakkinen finished last season the more convincing of the two, even if Coulthard was placed higher in the championship. That might be seen as a psychological advantage for the Finn, although not by Coulthard.
He said: "Mika's quick and had some good races towards the end of last year, but that could be down to the fact that those particular circuits suited him. Perhaps I'll find the circuits early in the season suiting me again. Mika's form certainly hasn't affected my confidence. I believe in myself and always have done. I'm not saying I'm going to do that or the other, just that I know if the car is OK I can deliver the results."
Northern Ireland's Eddie Irvine is the only member of the leading teams not permitted ambitions of the championship, even if his car proves the best in the field. However, he still has to convince a sceptical Italian audience he is deserving of the Ferrari seat alongside Michael Schumacher.
Irvine's times in testing have compared favourably with the German's and he is in apparently good spirits, but non-committal about his prospects for the season.
He said: "I'm feeling reasonably good but you never know until the season starts. I think we have worked well and should be pretty good, but we'll find out soon, won't we?"
Johnny Herbert, the Englishman at Sauber, confronts an intriguing domestic duel with a new team-mate, the gifted but tempestuous French-Sicilian, Jean Alesi. "So far there hasn't been any problem, he's been easy to get on with," Herbert said.
The testing has been less encouraging. Herbert described a recent stint at Barcelona as "the worst I've had at Sauber". Reliability has been the elusive factor.
Many respected observers believe the new regulations, introducing narrower cars and grooved tyres, ought to suit the unfulfilled Herbert. The pity is he will again be stuck with a midfield car.
Brits on the grid
Damon Hill (Jordan)
Age: 37. Races: 84. Wins: 21
David Coulthard (McLaren)
Age: 26. Races: 58. Wins: 3
Eddie Irvine (Ferrari)
Age: 32. Races: 65. Wins: 0
Johnny Herbert (Sauber)
Age: 33 Races: 113. Wins: 2Reuse content