Facts
5 The Company was incorporated in June 2004 by the Appellant and a Mr Allan Hartigan. Their plan was that the Company would acquire a particular parcel of land at Lot 30 Denman Road, Muswellbrook ("the Property") that then had a rural zoning, obtain a rezoning of the Property, and subdivide it into residential lots. The Appellant and Mr Hartigan each held half the shares in the Company, and each was a director.
6 In August 2004 the Company exchanged contracts to purchase the Property from its then owner.
7 Soon after exchange of contracts, Mr Hartigan told the Appellant that he no longer wished to be involved in the transaction. From then on, the Appellant was in effect the embodiment of the Company, but he did not actually acquire Mr Hartigan's shares until 9 November 2004.
8 The Respondent is a property consultant. In about mid October 2004 the Appellant and the Respondent met, and the Appellant told him that he needed a new partner in place of Mr Hartigan. The judge found that the Appellant "expressed confidence that he could successfully arrange for rezoning of the property to rural residential."
9 Notwithstanding that contracts to purchase the Property had been exchanged on 4 August 2004, with a deposit being paid by Mr Hartigan from his personal funds, there were no arrangements for obtaining finance to complete the purchase.
10 The Respondent was at the time in a de facto relationship with Ms Karin Schulz. The Respondent asked her to finance the project.
11 On 1 November 2004 there was a meeting in Muswellbrook between the Appellant, the Respondent, Mr Hartigan and Ms Schulz, at which the document whose meaning is in contention in this appeal was executed by the three men. The provisions that are presently relevant are:
"(b) The purpose of this aquisition [sic] is to endeavour to have the said property re-zoned to Rural Residential and ultimately develop the area into a number or [sic] allotments. For the benefit of this agreement, a time frame required to finalise the re-zoning is 2 years. If this time frame proves to be insufficient, the parties agree to negotiate an extension based on the likelyhood [sic] of re-zoning being imminent.
(c) In the event of the re-zoning being approved, Noel Turner (or his nominated company) agrees to pay to Allan Hartigan, an additional sum of $350,000.00, being payment in full. These funds are to be made available to Allan within ..90 days.. [sic] of approval of the re-zoning. Furthermore, I Brett Kirkby, upon the re-zoning being approved, agree to pay to Allan Hartigan the sum of $225,000.00 being payment in full for 50% of the 42 acres and the inventory attached thereto.
(d) In the event of the re-zoning being unsuccessful, the abovementioned clause (c) will be abrogated thus making any further payment by Noel Turner or Brett Kirkby to Allan Hartigan null and void. Furthermore, all interests held in "UPPER HUNTER DEVELOPERS" will be terminated and transferred in full to Noel Robert Turner (or his nominated company). The implementation of this facility will see Noel Turner as the owner of the property in it's [sic] entirety.
(e) I, Brett David Kirkby, agree to take responsibility for the co-ordination of the re-zoning procedure including liaising with all parties and Government bodies with an interest in it's [sic] successful implementation[.] Further, I agree that Noel Turner be given the responsibility to co-ordinate the development procedure in consultation with myself."
12 The purchase of the Property was settled on 10 November 2004, after Ms Schulz had paid the solicitors acting for the Company on the purchase an amount of $450,000 to fund the purchase. The Property was transferred to the Respondent and the Company as tenants in common in equal shares.
13 With the express authority of both the Appellant and the Respondent, the solicitors who had acted on the purchase delivered the Certificate of Title for the Property to the Respondent. He passed it on to Ms Schulz.
14 The Appellant engaged various firms to work on the proposal for rezoning of the Property. However, no rezoning had been achieved within two years of the date of the Agreement. Indeed, by the date of the hearing in the court below (5 November 2007) the rezoning had not been achieved.
15 The evidence established that the Council had prepared a draft local environmental plan (the draft plan) for the whole Shire which was intended to replace Muswellbrook Local Environmental Plan 1985. The appellant had submitted a request to the Council in December 2005 to rezone the Property to Rural Residential which was included in the draft plan. However, there remained a number of issues with respect to the lot size which would be permissible within that zone and which had still to be resolved with the relevant government departments. On 18 June 2007 the Council resolved to adopt the draft plan for the purpose of undertaking consultations with the Department of Planning over outstanding issues and to seek a certificate under section 65 of the Environmental Planning and Assessment Act 1979 to progress the matter to the public exhibition stage.
16 That certificate had not issued at the time of the hearing. There were still several steps to be gone through after issue of a certificate (if it ever happened) before the draft plan could be made and gazetted by the Minister and thus come into force. It was common ground that at the time of the hearing the applicable zoning was not "Rural Residential".