Henry and his children (daughter "Perry" is the only one mentioned by name) are included in the will of his brother William of Nottingham, England. He probably came to New England about 1636, and then in Springfield, Massachusetts. He probably came over with five children and perhaps a wife. His property in Springfield eventually became the court square. Henry is mentioned in Stratford, Connecticut, records in 1647, when his son John described him as old and having failed eyesight. An inventory was ordered for Henry's estate with John as the administrator on 19 June 1665.
An extensive court case involving the Gregorys appears in the New Haven court records for 1647:
"John Meges declareth that at two severall times or agreements, he bargained with Henery Gergory of Stratford to make 14 dosson of shooes, and was to give hime 12d a pare for making them, carying them to hime readie cutt out. That he payde 48s of this before hand, and 6l more he was to have when he had done halfe the worke. He was to doe it well and sufficiently. That Goodman Gergory hath made 13 dosson of them, but they are all naught and fall in peces, some in a weeke, some in 14 dayes time, so that the plantiffe is damadged both in his name and estate. In his name, bothe at Connexticote, Long Isalnd, Totoket, Guilford, Stratford, Farefeild, they all cry out, and some thinke the plantiffe worthy to be putt in prisson. And by reasson of it he further saith, he hathe bine forced to breake ingadgments wth Mr. Evanc, whoe should have received 30l worth of this ware, and he turned it backe as unmarchantable, and what damadge will come further, he knoweth not. Beside it hath hindered hime in his trade to his great damadge, he being on that deales wth many people, they have shuned to by any ware of hime. The pantiffe further saith that Goodman Gregory hath not onely made the ware badely, but hath spoyled the leather by layeing them in the sand - that some of them are rotten, they were ptly covered wthin and wthout, and the pttye that fetched them was faine to washe them to make them cleane. Further he hath altered the propertie of the ware, for whereas he should have made some wooden heeles, and had wherewthall to doe it, he made them plaine, and by that is Mr. Evanc disapointed allso; and some of them he hath made a size shorter then he should, and some of the 9, marked them wth the 10. He complained for a lasst I sent hime one, yett he made them as he did before. Lastly the plantiffe saith, it is to his hindrenc that he had laide out this money so longe before hand.
Henery Gregory, the deffendant, saith, that he received a hide from John Meges at 48s pric, for which hide he was to make hime 4 dosson of shooes wch came to 48s; pt of this he did before the other bargaine, and he sawe the ware and accepted it, and Mr. Evanc tooke it as currant and good, but it proved not so. The plantiffe seing this ware, agreed for the rest, but hee, this deffendant, before the agreement, told the plantiffe he would make no more of such leather. The plantiffe promised bothe better leather, and to procure hempe from Connecticote to sow the showes wth, but did not performe accordingly, so that the deffendant was forced to buy flax at 18d p 1, and sowed them wth flax. The plantiffe bringing more worke, the deffendant saith he told hime the bargaine was to carye away that was done, he said it laye better then he could laye it, so left some of it till the 3th or 4th of November. The deffendant minded hime of his promise to bringe better leather, & told hime, this is as bad or worse then the first, that if he had not better leather he would doe no more, and added, it is pittie but the tanner should be hanged wch tanned it, for he cossens the cuntrye, but he said it was not the tanners fault alltogether, he the plantiffe was fame because of Mr. Evanc his hast, to take it out when neither the tanner nor himselfe could tell wheither it was tanned inoughe or no. The deffendaut dissiered to have hemp, the plantiffe said that thred would last as longe as the leather; so this deffendant went on and did the worke, all but on dosson, but he neglected to fetch them awaye. Some leather the plantiffe, or some for hime, left at Moses Wheelers, wch his wife tooke up & rent the graine from the flesh, and some of the leather is to be seene in the towne at Mr. Evanc his house. The defendant saith further yt he tooke out ye best pare of shooes he could picke out of the first 4 dosson; Mr. Blackmans sonn had them, and in a short time they tare out in the whole leather. For makeing the showes lesse then they were cutt out, it was because they were marked by hime more then they would reach, for some wch was to be made up of ye tens, would not reach a nynes last, but would teare, they were so little and the leather so bad. And for markeing them longer then they were made, it was because he sent me word that I should marke them as he had marked them; and secondly, he sent me a last of the tenns, wch was not of ye tenns. The deffendant further saith, that he lost 15 weekes time by the negligenc of John Meges, for want of worke, contrary to agreement, as appeares in the wrighting. And for makeing the wooden heeles shooes other-wise then hee appointed, it was because the deffendant was faine to take those rands to make welts for the plaine shooes. F'or this the court blamed hime, telling hime he should have forborne makeing them till he had bine supplyed wth matterialls, but Goodman Meges saith he sent welts wth all the shooes he sent.
The plantiffe and deffendant having spooken, wittneses were called and examined.
Jonathan Sargant testifyeth upon oath, taken before the governer, the 22th of October 1647, that he buying a pare of russitt shooes, clossed in the inside at the side seames, of Goodman Megs, he wore them at the first 2 or 3 times to a neighbours house, but did not, that he knowes, then wett the soales of them; secondly he wore them onc at the meeting, being aboute 40 rode; 3dly he wore them one more to the meeting; that night he walked downe to ye watter side, aboute 60 rod from his house, and then he brought home ye soales of on of his shooes in his hand, and the other lose, readie to fall of; then he gott them sowed againe, and wore them now and then, but not constantly, for a weeke or a fortnight, then the insoales and outsoales and all fell from the uper leather; he cannot remember that he wore them any more then this.
Thomas Whitewayc dothe testifye upon oath, that he bought a pare of russit shooes of Goodman Meges of Newhaven, clossed in the inside at the side seames; he wore them 3 or 4 dayes and then the out soales ripped, then he sowed them againe and wore them 3 or 4 dayes more, and the insoales, welts and all came of, then he sowed them together againe, and shortly after the upper leather, seames, heeles and sides ripped, so as that they would not hange vpon his feete, the uper leathers being not broken, nor the out soales so much as broken at the toes, insomuch that this deponent said, he thought it was fitt Goodman Megs should be putt in prisson for so coussining the cuntery, and he doth expect sattisfaction from Goodman Meges.
John Parmele of Guilford testifyeth upon oath, taken before Mr. Disbrowe, the first of November, 1647, that he bought a pare of shooes wch came from Goodman Meges of Newhaven, russet, clossed in the insides at the side seames, and that wearing them but 6 dayes, or 7 dayes at the moste, the soales ripped from the uper leathers.
Samuell Netelton of Totokett doth testifye upon oathe, taken before the governer, the 4th day of November 1647, that he bought a pare of shooes of Goodman Meges of Newhaven, russed, clossed in the inside at the side seames, for his wife, she put them on on the Lords day, and the next third day morning they weare ripped, the soales being good, neither shranke nor hornie that I could perceive. And he also testifyed that for and in consideration of satisfaction from Goodman Megs, he expecteth a new pare.
Marke Meges testifyeth upon oath, taken before the governer, the 16th of November 1647, that he being at Stratford to fetch home the shooes that were made by Henry Gregory for Jno Meges, he found the shooes lying in the sand, many of them being ptly covered wth the sand, bothe wthin and wthoute, so that he was forced to take awaye the sand with his hands to come at them, and handed them to Ralphe Loines, whoe handed them to old Gregory, whoe washed them in watter to wash awaye the sand and filthe from them. Allso he testifyeth that he seing the old man worke wth a very great aule and a small thred, wth very litle wax, blamed hime for it. That at that time they left some behinde that were not made.
Other testimonies were delivered in wrighting to the courte to the same purpose, but not upon oathe.
Goodman Gregory pleaded that it was the badnese of the leather wch was the cause of the shooes ripping and falling apeces, for the leather was hornie and not tanned. The court bad Goodman Gregory prove that.
Mr. Evane saith that being at Mr. Blackemans, they had speech of these shooes, Mris Blackman said that after 2 or 3 dayes wereing, the leather was like flaps of a shoulder of mutton; and Mr. Evanc further saith that he sold shooes of these to a ptie himselfe, and the leather was so bad that the ptie would not have them.
Mr. Blackman saith that his sonn had a pare of shooes of these, wch he thinkes lasted not above 3 weekes, then they broke in the whole leather, and another pare of shooes mended for another of his sonns wth some of that leather, wch in on dayes wereing, being wett, was spoyled.
Juda Gregory testifyeth upon oath, that he looked upon pt of the leather wch his father was to worke of Goodman Meges, and some of it was so hornie that according to his Judgment, no man could make shooes to pase his word on them to hold. Allso shooes so tainted, thoughe they might Seeme to be tanned, yet they would not hold that a man was able to justifye himselfe or the leather in it. Allso that his father complained to hime, this deponent, and himselfe sawe shooes of the tenns marked for elevens, that by a size he could not sowe them either for credite to himselfe or proffitt to the cuntery. Allso that Goodman Royes showed hime shooes he made for Goodman Meges and he could not last them, but was fame to sett them on a last a size shorter then Goodman Meges would have them made. Allso that Goodman Meges would have had this deponent wrought, but he sawe the lether so bad that if he never wrought more he would not worke it, in regard of the uncomfortablnese to worke, because it was hornie, and so litle that it would not come together, and because it would be a wronge to the cuntery. Further he saith that Goodman Royes told hime that he complained to Goodman Meges of cutting his shooes so litle, he stranged at it, but Royes told hime he lost by cutting his soales so bige and his uper leather so litle, but Goodman Meges said he did not use to doe so. For the lying of the shooes in the sand, this deponent saith he tooke a pcell, pare by pare, from the place where those laye that Marke Meges fetched away, and they laye, in his aprehension, wthout any damadge, wthout any sand in any pare that he coulde discerne, thoughe he cannot saye they wore the same pcell that Marke Meges fetched awaye, thoughe it was aboute that time.
Moses Wheeler testifyeth upon oath, taken before Captaine Astwoode, the 30th of November 1647, that Goodman Meges his mail left some leather at his house for Goodman Gregory, and the next day his wife tooke up some of it in her hand and said she thought it was tainted, and put it betweene her hands it did teare wth ease, and this he heard & sawe. Further he saith he heard Goodman Gregory at on time, (but wheither at ye time before mentioned he Can not tell,) that he was sicke of that leather, and that he should never have credit of it for his worke, nor they profitt that should weare it, and further he saith, that he speaking wth Goodman Gregory aboute a pare of shooes, he answered was not fitt to were in this cuntery, for it was to be caryed out of the cuntery, and that he durst not pase his word upon it.
The wife of William Crooker testifyeth upon oathe, taken before Captaine Astwoode, the 30th of November 1647, that when Goodman Meges came for the shooes, he sawe them lye upon a sandye bench in the sellar, and he said he liked the lying of them very well, saying to her father he could not lay them better. And her father finding fault with the hornynesse of the leather, that the flax would not hold it, Goodman Meges answered that the next weeke he would goe to Connecticote and gett hime hempe, but he said he thought the flax would last as longe as that leather, but after Goodman Meges was gon, and delaied to fetch awaye the shooes, her father wiped them wth a cloth, and tooke some clapbords and other things, and laide under them. And further she saith her father blamed the tanner for the leather not being well tanned, Goodman Meges answered he could not blame the tanner so much, for he was fame to take it oute before it was tanned. She saith further, she sawe it teare in peces when her father put it upon the last, and on shooe her father was faine to pece on the side.
The court having heard these things on bothe sides did thinke there was a fault in bothe, and that the cuntery was much wronged in this waye, therfore they were willing to call in some workemen, bothe shoemakers and tanners, that they might see it and judge whose the fault was, and so give into the courte what light they coulde. To this purpose, some of the shooes thus made was brought from Mr. Evanc, wch were some of the best of them, and the court called and dissiered Leiutenant Seely, Goodman Dayton, Goodman Grove of Millford, shoemakers, and Goodman Osborn and Seriant Jeffery, tanners, to take those shooes aside and veiwe them well, and if ther be cause, ripe some of them, that they maye give into the courte according to ther best light, the cause of this damadge. They did so, and returned this answer, Leiutenant speaking in the name of the rest. Wee aprehend this, that leather is very bad, not tanned, nor fitt to be sold for servicable leather, but it wrongs the cuntry, nor can a man make good worke of a great deale of it. And wee find the workemanship bad allso, first ther is not sufficient stufe put in the thred, and instead of hemp it is flax, and the stiches are two long, and the threds not drawne home, and ther wants wax on the thred, the aule is to bige for the thred We ordinarily put ill 7 threds, and hear is but 5; so that according to Our best light wee laye the cause bothe upon the workemanship and the badnesse of the leather.
Goodman Gregory, upon this testimony, seemed to be convinced that he had not done his pt, but then laide the fault on Goodman Meges, that he was the more slight in it thourough his incouradgment, whoe said to hime flap them up, they are to goe farr inoughe.
William Hooke junr testifyeth upon oath, that he clearly remembreth Goodman Gregory was makeing 2 pare of shooes in their shopp, Goodman Meges came in in the meane time, and he said to Goodman Gregory, flapp them up together, they are to goe farr inoughe.
John Gregorie testifyeth upon oathe, that Goodman Meges said, flapp them up together, they are to goe farr inoughe, this was aboute the beginng of the last bargaine, wch was for the 10 dosson.
Concerning the 15 weekes time, wch Goodman Gregory demaunds damadge for, that is to saye, from July to Nouember, it did appeare by Goodwife Meges her testimony in court, that she, from her husband, told Goodman Gregory at the faire in September, that her husband was discouradged to send hime any more worke because his worke was naught, thoughe hee had more worke readie cutt out.
John Gregory saith, that aboute the time of the bargaine he gave Goodman Meges some cautions, because his father was old and his eyesight failed hime, and he durst not imploye hime himeselfe, for he could not doe as he had done.
Mr. Evanc was asked the cause why he turned the shooes upon Goodman Meges his hand, he said the maine reasson was the badnesse of the leather, thoughe he allso excepted
Goodman Meges was called to propound his damadge, he instanced first in his name, 2dly damadge to Mr. Evanc, 3dly his ware being turned upon his hand, 4dly hindranc in his trade, 5dly money payde severall men for satisfaction.
The plantiffe and deffendant professing, upon the courts demaund, that they had no more to saye, and the court considering the case as it had bine presented, debated and proved, found them bothe faultie. Goodman Gregory has transgresed rules of righteousnes, both in refferenc to the cuntery and to Goodman Meges, thoughe his fault to Goodman Meges is the more excuseable, because of that incouragement Goodman Meges gave hime to be slight in his workemanshipp, thoughe he should not have taken any incouragement to doe evill, should have complained to Some magistrate, and not have wrought such leather in such a manner into shooes by wch the cuntery, or whosoeuer weares them, must be deceived. But the greater fault and guilt lyes upon John Meges for putting such untanned, horny, unservicable leather into Shooes, & for incourageing Goodman Gregory to slight workemanshipp, Upon a motive that the shooes were to goe far inoughe, as if rules of righteousnes reached not other places & cuntryes.
The Court proceeded to sentenc, and ordred Goodman Meges to paye 101 as a fine to the jurisdiction, wth satisfaction to every perticuler person, as damadge shall be required and proved. And further the court ordered that none of the faultie shooes be caryed out of the jurisdiction, to deceive men, the shooes deserving rather to be burnt then sould if ther had bine a lawe to that purpose; yett in the jurisdiction they maye be sould, but then only as deceitfull ware and the buyer maye knowe them to be such. They ordered allso Goodman Gregory, for his slight, faultie workmanshipp and fellowshipp in the deceipt, to paye 5l as a fine to the jurisdiction, and to paye the charges of the courte, and that he require nothing of Goodman Meges for his lose of time in this worke, wheither it were more or lesse; and the court thought themselves speedily called and seriously to consider how these deceipts maye be, for time to come, prevented or duely punished.
children of Henry Gregory:
daughter m. Richard Perry?
daughter m. William Crooker
Judah m. Sarah Burt
Elizabeth m. Richard Webb