In 1826 Henry Barclay established the paper mill in Saugerties and then transferred ownership of it to his father, Thomas Barclay. He'd turned his attention within the year to establishing the infrastructure of a large community. Thereafter the Barclay family ran the paper mill and built and ran other investments in Saugerties until Henry Barclay's death in 1851. At that time all the land and investments of Henry Barclay were sold at an auction except for the paper mill. Management of that was transferred to Joseph B. Sheffield and Norman White and ownership of this business was transferred to them in 1857. The capital investment that the Barclay family held was retained on the paper mill as mortgages until after the turn of the century and perhaps further. Norman White left in 1867 and in 1869 the business became J. B. Sheffield and Son as William R. Sheffield who was born in 1847 came of age. The equity stake of the Sheffield family in Saugerties businesses continued to grow from there.

William R. Sheffield grew up in Saugerties and took an active interest in local commerce and its relationship to transportation by forming the Long Dock Corporation. In the late 1870's this company constructed telegraph lines to the resorts in the Catskill mountains as part of his business objectives. It also made investments in several Catskill mountain resort hotels. When W. R. Sheffield served as president of the village his main objective was improvement of the street and sidewalk systems through the village to benefit visitors and haulers using the Long Dock ferry terminal as the principal link between the established railroad across the river and the new one on the west shore.

By 1882 the Ulster Iron Works and the Sheffield Paper Company, Inc owned all the lands of the mills on the south side of the Esopus. By 1887 the iron works had ceased production and William Mulligan, the owner, sold this property to William R. Sheffield for stock in the Sheffield Paper Company, Inc.

William R. Sheffield then joined with William Parsons to replace the iron works with the Barclay Fibre Company to make pulp from wood fiber, an experimental process at the time. For this expansion John G. Myers supplied a mortgage on the iron works land to support the construction and equipping of these new facilities bringing in the first outside capital other than that of the founders.

Every construction and operations investment during the nineteenth century was made with private capital. The investors were related by business or family and had continually been hands-on or eyes-on through established relations with Saugerties since its founding. There was no building, road, or merchandising business started in this era that was not related to Saugerties' founding industries.

Risk and gain were central to the events of Saugerties history in the nineteenth century. The only remaining nineteenth century mill still standing in Saugerties; “The Mill”; is an example of how the risk gambits played out.

Variously known as the blank book factory and the bindery, The Mill was built by Sheffield Paper Company, Inc and John Q. Preble, Inc., jointly, as the Blank Book Company in 1888 to replace operations lost by the Preble company in a fire the previous year. The year 1888 was taken from a chronology in the 1911 Saugerties centennial book but the date could be earlier. Preble, the pulp factory and Sheffield all shared the same address in Manhattan at 10 Thomas street so production efficiencies from pulp through paper making and finally a finished blank book product, with Preble's business planning to corner that market, may have been in the works for some time.

Half ownership of The Mill was part of the holdings of Sheffield, Inc. when it was forced into bankruptcy in 1889 due to a failure of J. Q. Preble, Inc and a subsequent cascade in losses from Sheffield's related Chicago sales operations expansion. This bankruptcy was resolved when the bondholders of the Sheffield Family Trust bought the assets of and became mortgage holders for Sheffield Paper, Inc in 1894, selling all operations to the New York and Pennsylvania Paper Company.

Parsons, whose Barclay Fibre Company was not part of the bankruptcy but had banked on the Sheffield/Preble plan, later voluntarily ceased operations separately in 1897 after J. G. Myers had taken possession of the iron mill property after the bankruptcy settlement as compensation for the mortgage he held on the pulp mill. The Sheffield's Long Dock Corporation involvement, a separate development under Sheffield, Inc., went to G. R. Spaulding, a partner in this company, who held a mortgage on its lands.

In the nineteenth century land was not as important as it is considered today. A mortgage on an improvement on land was the way an investment yielded income and created wealth. In the pre-Civil War years, as Saugerties made its reputation as an industrial center, those associated with investments in any improvement of the land here were considered as wealthy as ground floor investors in technology businesses are today. The relationship to the actual buildings or the land the buildings are on is even today incidental to the capital they represent as places of production.

It is thought that the Barclay family retained their investments in Saugerties well into the mid twentieth century through the early mortgage debt still owed them by the Sheffield family. That debt listed in the Sheffield Incorporated bankruptcy as owed to Thomas Barclay and to George Barclay was likely converted to bonds and assumed by the Sheffield trust. Collateralized debt provided the stable source of income that kept wealthy families going and bonds were their debt instrument of choice. The wealth of the early Dutch families was not in their large estates up the Hudson but in the small patches of land under the improvements of New York City they owned and leased or sold holding the mortgage.

After 1894 the Sheffield trust was solely interested as a land holder that either leased or was a mortgage holder of the mills it had sold. Barclays and Sheffields played no active part in the actual manufacture of paper but maintained that financial interest. It is that income that helped the Sheffield family carry on a lifestyle typical of the Golden Age with townhouses in Boston and upper Manhattan and Paris and memberships in the clubs where William R. Sheffield is known as a king maker in Republican politics associated with the lucrative paper interests as a leading investor in the industry, and its spokesman.

The Sheffield Family Trust leased the blank book factory it owned as the Sheffield Manufacturing Company to the Saugerties Manufacturing Company in 1894. It's owners divided the building into bindery operations in the west building and envelope manufacture in the east building. In 1894 the first embossed stamp envelopes under contract for the United States Post Office were made in the east building under a lease. By 1912 the Saugerties Manufacturing Company again occupied the entire Mill with bindery operations and had become the largest maker of the then patented ring binders with spring opening and its Sterling brand was the most popular packaged filler paper in the country. Their Sterling brand is still famous as the ubiquitous composition book.

F. L. Russell was brought in as manager for the Saugerties Manufacturing Company in 1929 and in 1936 he vacated the buildings and moved all operations to the Martin Cantine Co. Tissue Factory building on Ulster Avenue.

The Mill was leased to Knaust Bros in 1939. They were large producers of mushrooms and used old factories in Hudson and Catskill also as environments for cultivating mushroom spores that would be taken to limestone caves for growing. In 1941 they bought the property from Henry Hazen Reed who is said in the documents to be the last remaining trustee of the bondholders of the Sheffield Family Trust. Then in 1942 Knaust Bros leased the building to RCA for wartime production. In 1946 they upgraded the heating system and then leased it to GE.

In 1953 Knaust Bros sold The Mill to Northeastern Holdings who leased it to Ferroxcube for through 1964. After that the building sat abandoned for 35 years until it was converted to senior housing in the late 1990's.

The paper mill likely left the Sheffield trust in 1949 after the estate of Ralph Thompson, heir to Col. George Thompson, who had purchased the mill for the Diamond Mill Paper Company in 1903, sold it to a company called Flavicon, a maker of packaging for the food industry. At this time mortgages begin to be held by banks and a succession of foreclosures after Flavicon for Ulster Paper Company, the Ulster County Paper Company and the Empire State Paper Company are recorded from various banks right up to the late 1960's when the paper mill burned to the ground.

This transition from private to commercial debt after the war was what signaled the decline of innovative startups in Saugerties. The tradition that reserved opportunities and risks to the insiders of an investment community that began a century and a quarter before had even weathered the Great Depression. But it had been weakened by events that also affected the very soul of Saugerties.

All of the first generation of industrialists came to Saugerties for the investment opportunity. They passed this on to a second generation where Martin Cantine stands alone as being from a pre-Henry Barclay family. His father, Peter Cantine, was a lawyer and owned many farms. His father's sister's daughter was married to Edwin Gould, the son of the financier Jay Gould. Martin's brother Charles was his partner in starting the Martin Cantine Company and Charles was a lawyer and married to Mary Sheffield, a daughter of J. B. Sheffield. When Mary died when their daughter, Agnes, was just six, Charles, as guardian, became a trustee in the Sheffield Family Trust.

Martin Cantine began his management training in 1882 at the Sheffield paper mills when he was 16 and set up the Martin Cantine Company in 1888 when he was 22. He placed his factory on the north side of the Esopus on the land that had always been too high to have the advantages of the water for power. His business was a model of efficiency for its use of hydroelectric power and its process controls in paper coating placed its products in a stable market for nearly eighty years.

Martin Cantine began to involve himself in his father's native connection to the land when he acquired the estate of Mary Pidgeon in its bankruptcy sale in 1906. This was the large farm of the Kiersted family. The Kiersteds had been established in Saugerties for a half century before Henry Barclay arrived and the industries began. Their lands stretched from Main street at the Kiersted house to where the Cantine field, the high school and the HITS lands are today. This was all called “Valley Farm”. Martin Cantine's house was on the south side of Main Street, the second house east of the school, on a small rise that on early maps was called “cedar hill”, and looked out over the whole farm. In his will he donated the open fields opposite the school to the school board so that there would always be this open view from the now Cahill school's windows.

When Martin Cantine died in 1936 the Valley Farm was purchased from the estate by one of the companies run by the farm, the Little Sawyer Ice Company. They sold it immediately to Knaust Bros. In the late 40's the Knaust Bros created a grand plan that included a large medical and industrial research campus with a golf course and three story professional and apartment buildings, along with a technical high school and a merging of it all into the village through a residential sub-development. This was a very innovative concept for the time, as was their Iron Mountain document storage business in Columbia county. They called this Saugerties plan Farm Industries.

In 1948 the village annexed the part of Valley Farm's land designed for sub-development permitting the extension of streets, water and sewage. In 1958 the high school component of the Farm Industries plan became part of the school district's consolidation plan. The Cantine complex and the HITS improvements, and everything east to the river across Stromzeit was also on land dedicated to this plan and because of various interventions over the years ended up in their present uses.

There is evidence in the transaction record that the bonds involved in building the high school component if the Farm Industries plan, the bank debt incurred in this plan's development and bank mortgages covering the subdivision building it brought to completion, introduced commercial debt leveraging to the economy of Saugerties for the first time.

Holly Rudd Cantine continued the family ownership and management of the Martin Cantine Company until the company was closed in the late 1960's. Bank mortgages on the property taken by speculators follow the empty buildings until they burned in 1978. The property was foreclosed and in the possession of Chase Manhattan Bank at that time and its last remaining user of water powered status raised questions afterward about responsibility for the dam. That resulted in the first ever official examination of all the investments and title involvements going back to Henry Barclay.