An interesting one. Being an NUFC fan its something I've thought about, and I have no definite views on, so I'll run through what I have on it.
First of all, I'm going to step away from the original question, and look at other PODs.
1. What if Keegan hadn't walked on January 8 1997 (which happened to be my 18th birthday by the way. I still went out but the mood amongst our group, and throughout the city was somewhat subdued).
Anyway, had Keegan not walked, I'm convinced we would have gone on to win the league. Perhaps not that season (96-97), and in fact I wonder if we would have matched the 2nd place finish we achieved that year. When Keegan went, we were slightly off the boil and in I think 6th place. There were a lot of teams knocking each other out. With two games to go, Man U had it sewn up, but there was a three horse race for 2nd place between Liverpool, Arsenal and Newcastle.
The penultimate game was a big one because Newcastle were away to Arsenal. In the reverse fixture earlier in the season at St James' Park, Arsenal won despite being reduced to 10 men when Tony Adams was sent off. At Highbury, Newcastle got their revenge, winning 1-0, with 10 men.
That knocked Arsenal out of the race, but Liverpool were still favourites to take 2nd. Newcastle were relying on Sheffield Wednesday to at least hold Liverpool to a draw, and we needed to beat Nottingham Forest by 5 clear goals - a tall order despite Forest already being guaranteed relegation. But, Sheffield Wednesday held Liverpool 1-1 and we thumped Forest 5-0.
Kenny Dalglish had come in and at the time we were still playing the same passing, expansive, 'cavalier' out and out attacking game, but Dalglish tweeked the defence and had it tightened up, and the combination saw results improve and us rise out of our minor slump.
Had Keegan stayed I'm not sure he would have done that, but I do feel that it was a case of plugging away and he would have got there, simply through gaining experience and learning from mistakes. Being in the position we were in was new to Keegan (as a manager) and to the majority of the team. And it can take several attempts to get it right.
2. The 2nd POD comes during the close season in the summer of 1997. The club received an offer for striker Les Ferdinand of £6m from Tottenham. The club decided to cash in, claiming that the fee was a good price for a 30 year old. During the 96-97 season Ferdinand and strike partner had proven critics wrong. When Shearer signed in July 1996 for a then world record fee of £15m, many peopled wondered how the two would play in the same side - as both were centre forwards they would get in each others way. What happened was that they were a devastating partnership, because both were centre forwards, opposing defences weren't able to mark two centre forwards out of the game, so while one was being marked, they were creating opportunities by freeing up the other. Both strikers were also happy to play the supporting role when the other was in a better position to act as the main striker.
As Ferdinand, was tying up his deal with Spurs, Newcastle were involved in a four team pre-season friendly tournament held at Everton's Goodison Park. Unfortunately, Shearer suffered a tearing of his cruciate ligiments, which was to put him out of action until the following January, ie he would miss just over half the season.
Suddenly the strike force was depleted, with the responsibility falling on the incredibly talented but un predictable Colombian, Tino Asprilla - who was more of a play maker or supporting striker. Jon Dahl Tomasson, a 21 year old Danish attacking midfielder who had just signed that summer also had to step up, and unfortunately it didn't work, though Tomasson can't be blamed, he was young, inexperienced and being played out of position. It ruined his time at Newcastle, but he went on to Milan, where he proved to be a fantastic player.
Had the club rebuffed Tottenham's offer for Ferdinand, things could have been incredibly different. Shearer's still out of action for half a season, but we still have Ferdinand, with Asprilla playing the supporting striker. Tomasson in just behind them in his true position as the attacking midfielder- growing in confidence, playing in a good side and weighing in with his share of goals and of course, Ginola and Gillespie are still on the wings providing crosses for Ferdinand and Asprilla. In reality of course despite the memorable 4-3 win over Barcelona, things were pretty bleak, people were out of position and we weren't scoring. We were really struggling, and Asprilla and Ginola were soon unhappy and on their way. Everyone was desperately counting the days for Shearer to return and of course even when he did, it still took him time to find his feet after such a long lay off. With Ferdinand still at Newcastle, the pressure would not have been there, and Shearer could even have been allowed extra time to come back properly. We may have won the league that season. It would have been a case of picking up where we left off in 96-97. Instead, everything fell apart.
Finally, what if someone else other than Dalglish followed Keegan? The one most mentioned is Bobby Robson. The problem is that at the time Robson was in a tricky position. Robson had taken the Barcelona job in July 1996, on the understanding that it was a 2 year deal. (For the 96-97 and 97-98 seasons). As the 96-97 season progressed it became clear that despite Robson doing well (he guided Barcelona to European Cup Winners Cup, Copa del Rey and Super Cup victories and a 2nd place finish in La Liga), he would be replaced at the end of the season by Louis Van Gaal, and that he had really been appointed to keep the seat warm while Van Gaal saw out the final year of his contract at Ajax. Robson was to be kept on at Barcelona for the following season as a 'General Manager' on his same salary, a position he later described as being 'the most expensive scout in the world'.
At the time that Keegan left though, this was not known, so bringing in Robson at that point - or even holding on and going for him in the summer was not an option.
The only Bobby Robson comes in earlier scenario possible comes when dalglish was sacked a couple of games into the 98-99 season. At this point, now knowing Robson's situation, Newcastle did approach him, and he was tempted on the basis that he had been duped and that if he decided to join Newcastle he did not think that Barcelona would protest too much. However after much thought he decided that unlike Barcelona, he would honour his side of the contract and see out his remaining year upstairs.
Had he decided to take the Newcastle job, he would have had to do a bit of rebuilding and repair work, as he did when he arrived the following year after Ruud Gullit's disasterous year in charge. But it would have been a smaller job. He still had good players at his disposal. Alan Shearer and Rob Lee would have been spared their run ins with Ruud Gullit, whose treatment of Lee in particular was pretty disgusting. Other players such as Shay Given, Gary Speed, Nolberto Solano and Warren Barton would all play under Robson. Stuart Pearce and John Barnes were ageing players signed by Dalglish but both proved to be useful (even under Gullit) and were players Robson had managed as England manager. Who knows, Robson may well have been able to get more out of Stephane Guivarc'h and Andreas Andersson, both of whom proved to be little more than useless under Gullit. However both were internationals for France and Sweden respectively, indeed Guivarc'h was part of the French World Cup Winning Squad just that summer (1998) and had a good scoring record in France - so they must have had something about them. Robson was one of the most respected managers in the world, revered and loved by players, managers, officials, administrators and fans alike - one of the best man managers around. It would have taken a bit of time, and Newcastle would not have won the league that season (1998-99).
In reality, when Robson did arrive, Newcastle were again just a few games into the season (1999-2000), but were already rock bottom with confidence and morale amongst players and fans extremely low. He was able to come in and instantly raise morale (his first home game saw bottom of the table Newcastle destroy second bottom Sheffield Wednesday 8-0) and he guided Newcastle to mid table safety (11th I think?) that season and an FA Cup semi final as well.
Two seasons later 2001-02, Newcastle finished fourth, and then third in 2002-03, positions not seen since 1997.
If he came a year earlier and because there was less damage to fix, its possible he can achieve this sort of position at least a year earlier, so 2000-01. There may even have been a transient season (98-99). But, the position when Dalglish was sacked on August 27, 1998 was not at all bad. Newcastle had played two games and drawn both, 0-0 at home to Charlton and then 1-1 away to Chelsea. Had Robson come in at this point, Newcastle could have quite possibly had a very good season, even if we assume that his arrival could not prevent the 4-1 drubbing at home to Liverpool in the third game (this was just three days after Dalglish left, and Gullit appointed, as is often the way due to the short amount of time, Gullit did not take charge until after this game).
Had Bobby Robson come in at this point, its conceivable that with less to fix (and a lot of damage to morale was done due to Gullit's management style and treatment of some players), and coming a year earlier than OTL, that he could have guided Newcastle to the title.
Had any of these scenarios delivered Newcastle a title, I think more honours would have followed. What has happened is that under Keegan and then later under Robson, we were challenging, we came close but missed, and people like Freddy Shepherd thought tinkering about, would bring the success we were so close to, when in reality it caused disaster.
If the club actually got to a position where it won anything, especially under the likes of Bobby Robson, there would have been a legacy. Its an interesting thought, that if you bring Robson in a year earlier, he'd more than likely have brought his assistant with him, with Robson getting on, perhaps his assistant can offer more support, and enhance Robson, as had happened at Barcelona and at Porto before that. And at some point, there's a smooth transition when Robson retires and his assistant steps up to carry on the legacy. The assistant is of course, Jose Mourinho.