James Benson Underwood was born on September 18, 1838 in Canandaigua, Ontario, New York. He was the son of James Madison Underwood born 1808 in Vermont and his wife Lydia the daughter of Hiram Collins; she was born in 1808 in New York. The Underwood family can be traced back to John Underwood, born in 1585 in Dorset, England. His son Joseph born 1614 came to Hingham, Massachusetts in 1637. Many of our subject’s ancestors arrived in Massachusetts in the 1630’s. Our subjects father James Madison was the first of the family to be born outside of Massachusetts since the arrival of the families that make up his ancestral tree. Our subject’s great-grandfather David Underwood, born in 1742, served as a Private in the Massachusetts Militia during the Revolutionary War. His son David moved his family to Vermont before settling in Middlesex, Yates, New York. Our subject’s father James Madison Underwood went with his father to New York and after his marriage to Lydia Collins in 1829 they settled in Ontario County, New York, where their children were born. The eldest son was David Collins Underwood, born December 26, 1829. He was named for his father’s father and his mother’s surname. The 2nd son of the family was Hiram Collins Underwood, named for his maternal grandfather of the same name. The 3rd son born to the family was our subject James Benson Underwood. Another son Adam died young and a daughter Annar died when she was about 17. At the time of the 1850 census the family was found in Middlesex, Yates, New York. James M. was a Farmer with $5,500 in Real Estate. The household contained his wife, her mother Ann Collins, sons Hiram and James B, daughter Annar and 12 year old Ede Waters. Missing was David Collins Underwood. David had heard the call of the Gold Rush and had boarded a ship and sailed to California in 1849. In 1852 the father James M. Underwood died in New York.
D.C. Underwood Dead
“David C. Underwood, died at his residence in this city, August 14, 1882, of dropsy. He was born in Ontario county, state of New York, on the 26th day of December 1829, where he resided with his parents in New York until the great gold mining excitement in California, in 1849, when he came to California by way of the Horn. He remained but a very short time in the Golden State, and in 1850, sometime in December, arrived in Oregon, at the mouth of the Umpqua River. Sometime in 1851 he Made his way up the Umpqua river, and settled on a farm a few miles southwest of Oakland, Oregon. He was elected probate judge of Umpqua County in 1854, and filled the office faithfully. During the rebellion Mr. Underwood enlisted in the army where he held the rank of first lieutenant. He was in the service some four years, and after being honorably discharged he sold his farm in Umpqua and removed his family to Cottage Grove in this county, where he formed a partnership with Mr. E.W. Whipple and engaged in the mercantile business, and succeeded well. Some three or four years ago Mr. Underwood sold out his business at Cottage Grove and removed to Eugene City, and engaged in business with his brother, the late J.B. Underwood. Mr. David C. Underwood was a man of sterling worth, an excellent citizen, a kind and generous neighbor, and an affectionate father and husband. He leaves a large family to mourn his untimely loss, and a wide circle of friends, here and in the Umpqua. His generous hospitality and genial disposition made his house a resort, far and near, by neighbors, friends and strangers who lived in the Umpqua.
He belong to the order of Masons and A.O.U.W.; the orders joined in paying the last sad tribute to his memory, the Masonic order occupying the first place for the reason that he was a member of long standing in that order. Thus another chapter of human life is ended, and a worthy citizen gone to his long home.”
In 1859 James Benson Underwood, than 20 years old, boarded a ship sailing out of Angelica, New York around the Horn to California and on up to Oregon. He went to Douglas County where he joined his brother David. Prior to the June Communication of the Grand Lodge in 1859, D.C. Underwood had taken the first two degrees of Masonry. He was a Fellow Craft Mason in Winchester Lodge #16 in Winchester, Oregon. There were 19 members of the Lodge, which meet on the Friday before the full moon each month. David completed his degrees and was Raised a Master Mason and by December. Whether by a show of competency or a dire necessity he had gained enough confidence from his Brothers to forego being a Warden first and was elected Worshipful Master for the year 1860. He was elected again for 1861. On September 19, 1861 the Lodge changed its name to Oakland Lodge #16. Then in the Spring of 1862 the Master of Oakland Lodge #16 wrote the Grand Master, Dr. James R. Bailey, “stating that by a vote of said Lodge, they desired the privilege of surrendering their Charter, as they were all either going into the army or to the northern mines.” The request was granted and the Lodge ceased activity. As noted David enlisted and served as a Lieutenant for the next four years. David Underwood appears again on June 21, 1871 as the Charter Senior Warden of Cottage Grove Lodge #51.
J.B. Underwood applied for the degrees of Masonry in Winchester Lodge #16 in the Fall of 1860 or Spring of 1861 in the Lodge where his brother was Master. He is listed in the 1861 Annual Communication as being a FC in that Lodge. However, having relocated to Eugene a request was made on his behalf for a dispensation from Winchester Lodge, allowing Eugene City Lodge #11to confer the Master Mason degree upon him; this was granted. Brother Underwood was Raised a Master Mason on June 24, 1861 in Eugene City Lodge #11. In November of that same year he was elected Secretary of Eugene City Lodge #11 for 1862. He continued in that position in 1863. He did not serve as an officer for the next couple years before returning in 1867 when he was elected Master of the Lodge. He was elected Secretary again for 1881 and died in 1882.
Resolved: That Eugene City Lodge No. 11 A.F.&A.M. do hereby request Winchester Lodge No. ___ A.F.&A.M. to grant this Lodge a dispensation to confer the third degree on Bro. J.B. Underwood now a fellow craft belonging to said Winchester Lodge, by request of Bro. Underwood.
John C. Ainsworth’s Scottish Rite Records May 1870, page 1
James Benson Underwood received the degrees Dec. 18, 1871, page 13
- B. was an attorney living in Eugene City when he received the Scottish Rite degrees 4°- 32° inclusive on December 18, 1871 from Ill. Brother John C. Ainsworth 33°. He was the 31st member to receive the degrees in Oregon and the first Mason from Eugene to join the Scottish Rite. He affiliated with the Portland Bodies on July 2, 1872. He was later granted a demit on May 15, 1877.
Hon. J.B. Underwood Dead
“Mr. J. Benson Underwood, of this city, died at his residence, on Thursday evening, August 3, 1882, at 6:30 PM, of dropsy, after an illness of several months, but only six weeks confinement to his bed.
Mr. Underwood was born in Canandaigua Co. New York, September 18, 1838, his age at the time of his death being 43 years, 10 months and 15 days. He came to Oregon in 1859, and settled with his mother’s family in Douglas County. Desiring to study law he came to Eugene City in 1861, and he and the late J. M. Thompson both engaged at the same time reading law with the late Hon. Stokely Ellsworth. In 1863, Mr. Underwood was admitted to practice law, at once formed a partnership with Mr. Ellsworth, which continued until 1865. In 1866, he formed a partnership with Hon. G. B. Dorris, which continued until 1868. Mr. Underwood held many important positions of trust during his lifetime, and was never satisfied at being idle. He was elected school superintendent of Lane County in 1863, was elected to the legislature in 1865, was a partner in the Springfield Milling Co. for many years and also engaged in merchandising with the late Judge Stratton at one time, and Mr. S. H. Friendly at another time. He then became a partner in the Eugene Milling Co. and also engaged in merchandising with Messrs J.G. Gray and T.W. Osborn. Upon the election of Grant to the Presidency the first term he was appointed Postal Agent for the Oregon Division, which position he held for two years. He was twice elected President of the Common Council of Eugene, and several times a member of the Council. He was one of our most enterprising, public spirited and liberal hearted citizens, and took a lively interest in every proposition to advance the welfare of the city, which fact will make his death a great loss. He leaves a wife, three daughters and one son to mourn his death. The deceased was a Mason of 20 years standing, and was buried by that order at 3 PM yesterday, the business houses remained closed during the funeral.”
As noted he was elected President of the first town council with Eugene Skinner serving as Mayor. After the death of Skinner the position of President of the Council was essentially the same as being Mayor, and the current list of Mayors starts with J.B. Underwood. As Postal Agent he covered an extremely large territory and he travelled extensively, including trips to southern states in pursuit of mail robbers.
He built the finest residence in Eugene, “where the charm and beauty of the three daughters, made it a gay and popular meeting place for the younger generation.” After his death at age 44, his widow converted it into a boarding house for UO students. She probably had to do this to pay their debts. Her husband’s obituary, after praising his brilliance, boldness, and energy, said that “the principle cause of his financial reverses and death was the too free use of strong drink.” As will become apparent his affinity for gambling also attributed to his financial difficulties.
Resolved: That Bro. J.B. Underwood be requested to sit for a picture for the use of the Lodge and an order be drawn on the Treasury for payment of the same. (picture found at beginning of this article)
Among the other enterprises which involved Brother Underwood, was real estate. In 1866 the Lodge was paying rent to H.C. Owens and Brother. In November a committee was formed to determine whether or not to terminate the lease when it ended in 1867. Around March the committee approved the lease submitted by Underwood and Stratton. Underwood was Master of the Lodge at this time. The Lodge continued to pay rent to Underwood and Stratton for the Lodge building at the NE corner of 8th and Willamette through 1868. After which the payments were made to Underwood alone. On January 1st 1872 Brother Underwood offered to sell the building and lot, (24 x 120) for $4,000 to the Lodge. The committee did the math and did not find this to be a workable idea. Brother Underwood was then allowed to withdraw the proposal. The Lodge paid another years rent and in early 1873 a new proposal was submitted. This time Underwood and Norris Humphrey, in a document dated Jan. 15, 1873, offered to sell the building with a smaller lot (24 x 95) for $2,700. This time the Lodge accepted the offer paying $1,000 down and $460 a year until principle and interest were paid off. In 1877 J.B. Underwood presented a proposal to rent the downstairs portion of the building for a Wells Fargo Express office and Pharmacy. This offer was rejected in favor of Brother Horace Crain and the Crain Brothers Jewelry store which occupied the space for many years.
Proposal to sell the building to Eugene City Lodge #11 by Underwood and Humphrey Jan. 15, 1873
The Trial of William Osburn
In September of 1872, just prior to the general election, in which President Grant won a second term, Brothers James Benson Underwood and William Osburn made a $20 bet on the State election in Pennsylvania. Early in October Brother Underwood met Brother Osburn on the corner of Willamette and 8th Streets, where Brother Osburn paid him the $20. Later that same day while passing Mark Stevens Store, Brother Osburn expressed a desire to win his money back and after much bantering they agreed upon a bet. Brother Underwood bet Brother Osburn $20 that New York would go for Grant, and $20 Pennsylvania would do the same in the upcoming Presidential election. Brother Underwood expressed the thought that this would likely result in a split with neither winning nor losing. Brother Underwood pulled out two $20 gold pieces and offered to put them into the hands of Mark Stevens, but Brother Osburn said no, “it was too long to stay without the use of the money, we are both members of the same lodge and ought to understand each other.” Brother Underwood said alright and shook hands over the bet after calling Mark Stevens to witness. The morning after the election, having seen how the election had generally gone throughout this State and the Country, Brother Underwood took $200 from his safe and went down the street to bet it on the elections. Benson had been with the telegraph operator Frank Colman until he closed at midnight, and was told indications were every Northern state went for Grant. He ran into Brother Osborn in front of his store talking with Brother Bristow. Brother Underwood “upbraided” him for his foolish bet and asked for his $40. Again Brother Osburn wanted to get even and negotiated a change in the parameters of the bet. After some debate they agreed to the same bet, with this difference, New York would go for Grant by 25,000 and Pennsylvania by 50,000 – each bet being separate, totaling $80. Brother Underwood took out his money and put it the hands of Brother Bristow. Brother Osburn went into his store, supposedly to get the money. He returned empty handed and said that there was no need to put the money up front, saying “we are all Masons and our words are good to each other”. They called Brother Bristow to witness the bet, which he wrote down and put in his pocket. Again Brother Osburn lost the bets, but this time he accused Brother Underwood of already knowing the outcome when he made the bet. Brother Underwood said he would swear out an affidavit that he had no such knowledge and went to talk to Brother Bristow, who agreed the bet should stand and that it was not possible for anyone to know the majorities in these large states the morning after the election. William Osburn refused to pay the debt and after four years Brother Underwood made a formal complaint to the Lodge having exhausted all efforts to resolve the matter. Brother Underwood stated that his attempts to settle the matter had been futile and that “much hard feeling has been engendered and many hard words spoken over the matter”. Brother Osburn held an account against Brother Underwood of about $100, which Underwood refused to pay until Osburn would pay what he owed. Finally Brother Underwood agreed to take half of what was owed him and would settle the matter through an intermediary. Brother Osburn agreed and Brother Underwood sent him a list of eminent Brothers from the Lodge. However, Brother Osburn then rejected the notion and started a law suit to collect on the account held against Brother Underwood. At his wits end Brother Underwood submitted the complaint to the Lodge in a letter dated July 19, 1876 on the official stationary of the Office of Special Agent Post Office Department for Eugene City, the office given to him by President Grant. After describing the situation Brother Underwood closed his missive hoping that “wisdom, justice and right will dictate, believing that Brethren should dwell together in harmony. I am willing to lay all my grievances before you and abide by your decision.”
On December 28, 1876 the Grievance Committee met and took statements. The Committee determined that the two brothers bet and swore that if they lost they would pay up, that Osburn indeed lost and refused and still refuses to pay, and that the matter should be refered to the Lodge for a Masonic trial. On January 15, 1877 a Special Communication was called and Lodge was opened on the MM degree. A Masonic trial was commenced and both Brothers Underwood and Osburn plead guilty to the obvious charge of gambling. Some of the witnesses were heard on the 15th, but much of the case was heard and decided on January 22, 1876. As it stood William Osburn bet J. Benson Underwood $20 and lost, he doubled down and lost again now owing $40, he again doubled down and lost $80. He then changed tactics and stated that Underwood had cheated and known the results before the bet, saying that he had spoken to Frank Colman the telegraph operator just after the bet was made and that Colman told him that Ben Underwood already knew the results. Problem was that upon examination Mr. Colman stated he had no such conversation with Osburn. Mr. Mark Stevens was also called, his account agreed with Brother Underwood’s assessment. Osburn’s testimony differed in a few key ways. First he stated that the original bet in 1872 was for $40 and that he only paid half and never paid the other $20. He also stated that he tried to bet Underwood the night before the presidential election but Underwood wasn’t interested, changing his mind in the morning and making the majority bets as noted. However Osburn’s witnesses did not agree with him as to what was said and what happened. Underwood’s best witness would have been Brother William Bristow, but unfortunately he had died in 1874. Under cross examination Osburn admitted that he sued Underwood for the money he owed for paint, but did not deduct the money that he admitted he owed Brother Underwood. The evidence being heard and the trial coming to an end the ballot was spread on the guilt or innocence of Brother Wm. Osburn. There were 26 voting members in the lodge for the vote. In spite of pleading guilty from the start to gambling five brothers voted him not guilty of the gambling. The majority felt there should be punishment of some sort but the majority rejected suspension. As to the matter of Osburn violating his Masonic Obligations; 10 found him guilty and 16 innocent, as such he was deemed not guilty. The punishment was a reprimand given him by the Worshipful Master Joseph G. Gray. Brother Underwood did his best to abide by the ruling of the Lodge, but eventually it ate at him. On January 15, 1879 he wrote a letter to the Lodge in which he stated “I cannot and will not fellowship with members who are now received and accepted as True men and Good Masons in Lodge and in order for harmony to prevail and the great and good purposes of this noble and charitable order may not suffer on my account.” To that end he paid up his dues and made the request for a demit. Cooler heads must have prevailed and talked him down as his demit was not acted upon and Brother Underwood continued his membership in Lodge #11 until his untimely death.
In February 1880 Brother Underwood headed a committee to buy an organ from the Crain Brothers Jewelers. A deal was struck with the York Rite R.A.M. Chapter #10 to split the cost with Eugene City Lodge #11. They did however forget to buy the stool, which was picked up by Lodge #11 to the relief of the organist.
Brother Underwood fell ill in the Spring of 1882 and by the beginning of July he had become bed ridden. He developed Dropsy, now known as Edema, an abnormal accumulation of fluid in the interstitium, located beneath the skin and in the cavities of the body, which can cause severe pain and manifests as swelling. On July 5, 1882 the Lodge paid a nurse $20.50 for service to Brother Underwood at a rate of $3 per day. This continued on until his passing. In total the Lodge paid $184.50 for medical and burial expenses for Brother Underwood. Some of those bills are included below.
 Ancient Order of United Workmen
 Eugene City newspaper August 1882.
 Eugene Newspaper August 1882
 Cemetery Marker Eugene Masonic Cemetery.
About the author:
Michael D. Robinson 32° KCCH, was the second Master Mason Raised in Esoterika Lodge #227, and the first member Raised in that Lodge to serve as Worshipful Master. He was elected Master in 2013 and 2014, and currently serves as Historian. He is also Historian for Research Lodge #198 and Eugene Lodge #11 and District Deputy of District #13. Brother Robinson was appointed Historian of the Scottish Rite Orient of Oregon in December of 2014. He was the recipient of the “Novus Astorum” from the Portland Valley Scottish Rite in 2010, and the Hiram Award from Esoterika Lodge in 2012. In March of 2015 he was made Secretary of the Eugene Valley, and Director of the Work for that Valley in January of 2017.