The 68-year-old contracts manager said it was because of dwindling numbers, the transitionphase between red and white-ball cricket (one-dayers), and the coloured clothing.
"The game was a bit tired in that era and we were struggling, Napier Marist were struggling and so were Napier High School Old Boys."
One night at the church hall at Wycliffe St in the winter of 1990 they had gathered to merge with Napier Marist club.
A lawyer and former first-class cricketer, Andrew Morrison, from the firm of Sainsbury Logan, had revealed to the gathering that former club member Jack Minett had bequeathed a handsome sum of money to the club.
Part of the condition of receiving that fiscal fillip was to ensure NTOB remained a single entity, which warded off any efforts to merge.
"So we found out the money had turned out to be the sum of $250,000, which in those days was quite a bit of money."
The Jack Minett Technical Cricket Trust was formed and funds were grown from investments through it.
"Now that trust is a lot higher than that and every year we get a nice income from it which helps us develop our junior cricket and get our senior players reasonably cheap cricket so that was pretty much a life saver for the club."
Caldwell said that was how Napier Marist and Napier High School Old Boys evolved into Napier Old Boys' Marist.
It's a memorable time for NTOB club chairman Les Kennedy, club patron Max Plested and Caldwell, who have been with the club since they left high school.
"We are all around the same age and we've been with the club for close top 50 years now. At that time in 1990 we decided we should try to set up things for the club in the future so it's all working out very well."
Caldwell said it was bonus that Peter Worley, who was with Taradale Cricket club, in 1991 crossed the floor to become the NTOB club captain.
With Worley's connections NTOB were able to woo the Wairarapa trio of former CD Stag and "Tech's best-ever bowler" Mike Pawson, Peter Ryder, Jesse Ryder's father, and Chris Jefferies.
"Ryder and Pawson stayed in Hawke's Bay but Jefferies went back to Wairarapa after one year but that was pretty much the start of the rebuild."
NTOB prems celebrated at their clubrooms last Saturday night but are remaining focused on representing the Central Districts region at the annual New Zealand Premier Men's Club Knockout Tournament in Auckland from April 11-16.
"We're off to Auckland again, which is something we're pretty proud of because it's the eighth time, so I don't think any other Central Districts club, since they brought the club national champs in, has gone to more than twice."
Caldwell said NTOB were the only CD representatives to have claimed the national bragging rights in 2002-03 after coming close to winning it in the summer of 1990-91.
"Jesse Ryder played for us then so he's in the team to go there again this year, 15 years later so that was a very successful team," he said of the CD Stags batsman and former New Zealand international who will have finished the four-day Plunket Shield first-class campaign by then.
The Texans also will be expecting Stag debutant and former New Zealand under-19 World Cup cricketer Christian Leopard, CD A representative Matt Edmondson and under-19 national representative Robbie Brigham to add impetus to the NTOB cause.
"We have a good bunch of older and younger guys," he said, revealing there was a tinge of disappointment in missing out on the Murray McKearney Memorial Cup in the Property Brokers-sponsored HBCA Twenty20 club final to Ruahine Motors Central Hawke's Bay by eight runs a fortnight ago.
However, Caldwell said the Texans were thin in depth because of CD A and university education commitments.
"Young Isaiah Lange also broke his hand so we were a bit down on numbers for a Sunday and we were well beaten by CHB," he said but delighted with Sri Lanka import Indika Senarathne's "magnificent innings" of 161 runs last Saturday.
"The amazing thing about Indy [Senarathne] is that he came to us because he wasn't happy at [The Station] Napier Old Boys' Marist as an overseas pro on the first year we won the [overall title] so he's been in all the six winning seasons as have players like Liam Rukuwai and Stevie Smidt."
Veteran batsmen Bronson Meehan was a "class player" but hadn't committed fully for a few seasons because of his commitments to his new career as a schoolteacher.
"Hopefully when he settles into his teaching a bit more we might see more of him in the next few years but I don't know."
Before that the Dale Smidt-coached side are channelling their energy into making the cut for the limited-overs playoffs on Saturday, March 17, as top qualifiers to keep their hopes alive on the MJF Shrimpton Memorial Cup on March 24.
Caldwell said they viewed NTOB to be under the old and new eras — when it was established in 1921 as Napier Technical College Old Boys and the 1990 renaissance.
"There was a technical college in town which was brick and clapsed but got smashed to bits in the earthquake in 1931 and was never rebuilt.
"When we revamped the club in 1990 and changed the constitution we dropped the 'college' from it to become Napier Technical Old Boys because we didn't have that nursery."
However, NTOB still sharethat college affinity with Napier Boys' High School through Pawson who coaches the first XI team there.
"We've got that link through high school to get players and this is where a lot of our players have come from, really, so there's been a lot of history there."
In the new era from 1990, the contemporary sides have amassed 20 titles "which is quite amazing, really".
In the thrust to groom homegrown talent, Caldwell said NTOB had had a significant Maori and Pacific Island player influx with the likes of Turner brothers, ex-team captain Ronnie and Ken.
"We've had a real good mixture of people and a sort of family atmosphere to the club."
During this era, the other big thing for the club was Craig Findlay, the Hawke's Bay Cricket Association chief executive and NTOB stalwart, had left NBHS and decided to join the club with younger brother Scott.
"We sport of see Craig as the first cricket development manager in Hawke's Bay before the David Blacks of Cornwall Cricket Club and that sort of thing."
Caldwell said Findlay had done a superb job while with NTOB, driving the revamping of its outdoor wickets as well as those at NBHS as an investment for the future.
"Of course we also set up the indoor centre through Craig as well," he said of the Whitmore Park facility with the help of former CD Cricket CEO Blair Furlong.
Findlay had started a junior club and his father, Harry, had rolled up his sleeves to coach in the nets.
"A lot of our players, like Christian Leopard and Todd Watson, who are guys coming through the national level, started at our junior clubs."