Wyllie was the son of a soldier in the Royal Scots Greys and was born at Piershill Cavalry Barracks, Edinburgh, in the part of the capital known as Jock's Lodge, now occupied by a council housing scheme. His father had fought at Waterloo. The exact date of Wyllie's birth has long been uncertain. It has been quoted as July 6th 1818 and July 6th 1820, with opinion divided on which is correct. My research has discovered that the true date is July 8th 1818. How this came about is explained in the accompanying article on this site, "Found at last - Wyllie's birthday". Wyllie was 80 when he died. At that advanced age his mind was still sharp, and he had not lost his skill or enthusiasm. He remained a formidable competitor. He had played draughts all through his life, making an important and indelible contribution to the progress of the game.

Biographical details given in draughts magazines in the 19th century say that Wyllie's father was discharged from the Army in 1826 and returned with his wife and family to Kilmarnock, their native place. My research has found a record in the National Archives at Kew that his father, Hugh Wyllie, died in Ireland in December, 1826, while serving with the Army (quoted here by permission of the National Archives). It appears now that Wyllie's widowed mother returned to the family's native place at Kilmarnock. It is known that young James was brought up in Ayrshire. From an early age he showed a retentive memory and was good at arithmetic In the early 1830's he saw youths of about his own age playing draughts. According to his own account, which he later gave to "The Draughts World", he was told after three months practice he was so stupid he would never become a "dambrod" player. This brings to mind stories of film stars a century later who were written off at the outset of their careers. The advice, instead of discouraging Wyllie, spurred him to renewed efforts. After much practice, he was able to give the best players in his locality the odds of a man and defeat them with ease. He was apprenticed in Kilmarnock to learn the trade of a carpet weaver, but this occupation did not suit his constitution and he abandoned it for the nomadic life of a pedlar. With a stock of hardware, he travelled through the surrounding countryside, disposing of his goods and combining this with displaying his draughts skill. As he arrived at villages and small communities, he would keep his eyes open for a "dambrod" and invite the owner to play. One of his first matches was at Kirkconnel, where he played Mr Lees, the district champion, for a small sum. Wyllie was reckoned to have no chance, but the 12 games ended with Wyllie having won nine, Lees one, and two drawn. He then did well at Douglas, which was considered to have strong players. His sternest test so far came at Biggar, where he faced the local champion, a farmer named Core. Wyllie succeeded again.

How did Wyllie come to be known as "the Herd Laddie"? It was at this stage he acquired the nickname he was to bear for the rest of his life. While at Biggar, he met a stock cattle farmer, Mr Porteous, who was a keen draughts player. Porteous saw the youth's expertise at the board and devised a plan to give the "cracks" in Edinburgh a pleasant surprise. Wyllie readily agreed to help Porteous in driving his cattle to the market in Edinburgh. At the capital, Porteous met a Mr Bertram and arranged a match against him for a shilling a game. Bertram readily agreed. He was caught in the snare. Stakes were doubled. Wyllie won game after game. Bertram occasionally got a draw. The account given of this encounter states that Wyllie scored 59 wins out of more than 60 games. Whether this story is accurate or has improved with the telling, the fact is clear that Bertram was utterly routed. Wyllie profited. The account goes on to say that Bertram was eager for revenge and another match was arranged, but on unequal terms. Wyllie had to win 10 games before his oponent won one. The result was another inglorious defeat for Bertram. Wyllie's exploits in Edinburgh were not done. Other players came forward to face him. In matches of 10 games and a £10 stake, he defeated McFarlane 8-0-2 and Smith 9-0-1. Word of his exploits spread and he became the hero of the Edinburgh players, who gave him their support and encouragement.

Wyllie now met, for the first time, Andrew Anderson of Braidwood, Carluke, seen by his contemporaries as the champion player of Scotland. My research has discovered that this was in March, 1839. Anderson has a special place in draughts history. He was the first man to be recognised as world champion and wrote one of the classic books on the game. The match at Edinburgh, for a £10 stake, ended in defeat for Wyllie. A second match between the pair was hard fought but ended with the same result. Wyllie was not discouraged, because he was prevailing elsewhere. He defeated George Wallace, of Glasgow, who later became his life long friend, and won two matches against Steel, of Kirkconnel. He travelled south of the border about 1840. In a match against Price, of Manchester,who was considered to be the champion of England, Wyllie shocked the Sassenachs by winning 11 games to Price's two. On his return to Scotland, he faced Anderson a third time for a stake of £100. The contest was close and Wyllie lost again. He had now put all his opponents to flight except for Anderson. Wyllie's increasing ability was shown by the fact that he could make concessions, such as allowing his opponents to count draws as wins against him, and still come out in front. In another meeting with Price, he gave his opponent a start of seven games. Against Muirhead, of Macclesfield, he got 12 wins and five draws. In 1844, Wyllie challenged Anderson again. The match was played at Carluke and caused much excitement. It brought Wyllie's first success in the series, nine wins to Anderson's four, with several draws. The result did not please Anderson, who sought another trial of strength. A fifth match was arranged and was to be the last time they would meet. Played at Edinburgh in 1847, it is one of the most famous on record and is given in Joseph Gould's book, "Memorable Matches". Anderson had nine wins to Wyllie's six and there were 31 draws. Afterwards, Anderson retired from the arena and left the championship to Wyllie.

Wyllie now entered a match of a different kind. At Dunfermline, he married Helen Hendrey. The couple settled at Leven and began raising a family. Wyllie took part in no more matches across the board for about 10 years and appeared to have retired from the game when word reached him of the rise of a new star in the South. Robert Martins was sweeping all before him in England. It was inevitable that the two masters would face each other, and this took place at Edinburgh in 1859. Wyllie and Martins were to be rivals over the next 40 years. They tilted at each other in a series of epic matches.Martins was a Cornishman who settled at Douglas, Lanarkshire, from 1864 and became as much a part of the Scottish scene as the Herd Laddie. He should be remembered as an English winner of the world championship, but as the Scottish Draughts Quarterly said in 1896, he lived so long among the people north of Tweed that they looked upon him as practically one of themselves. In 1859, Wyllie was out of practice and Martins won by four games to one, with 43 draws. A newspaper report of the time states they were scheduled to play 50 games, and the contest ended after 48 games with Martins three ahead. His success in wresting the championship from Wyllie brought great rejoicing from his supporters. Wyllie returned to Leven and practised hard. He tried again against Martins in Glasgow in 1863, but a match in which the same opening was played over and over again ended in a draw. The two masters knew they could not get away with a repeat performance when they met for a third time in Glasgow in 1864, and this match was a splendid one with play which aroused the admiration of the spectators. Wyllie kept in the lead throughout and won by 10 games to five, with 47 draws. So he was champion again. He was to maintain his superiority in all future matches against Martins. A stubbornly contested match in Glasgow in 1867 ended with seven wins apiece. Wyllie's backers were not pleased that he had agreed to a drawn contest and soon after a match of four games took place in which Wyllie won two games without loss. In 1872 a match was played in England with games split between Leeds and Newcastle, and Wyllie won 4-3.

Wyllie was now internationally famous and was receiving invitations from across the Atlantic. The checkers players in the New World were eager to meet him. In 1873, Wyllie sailed from Liverpool for New York. He spent three years in the United States and Canada and played at Boston, Providence, Chicago, St Louis, Pittsburgh, Portland, Quebec and many other places. By his own record, he played 21,500 games, of which he won 20,694, lost 206, and drew 600. There were few big matches, because it seemed there was a reluctance among leading players to face such a formidable opponent. At Boston he met WR Barker, the champion of America, and won easily by 10 games to one with several draws. Wyllie's tour of North America was very successful, but it ended with one of the biggest upsets in draughts history. In New York earlier he had met a 15-year old boy, Robert Yates, who performed well against him. Yates became the strongest player in the New York area, and when Wyllie returned there in 1876 on his way home, a match of 50 games for the world championship was arranged. It was a tremendous struggle. Wyllie won the 33rd game and Yates the 47th. The final game arrived with scores level and 47 draws. It is one of the most famous games in draughts history. Wyllie had the move. Yates got into a losing position but Wyllie missed his opportunity. The advantage passed to Yates and he forced Wyllie back until he trapped him at the side of the board. Yates, still short of his 19th birthday, had wrested the world championship from the Herd Laddie by two games to one. Negotiations for a return match were begun but Yates later relenquished the championship as he had to begin medical studies. By common consent, the title reverted to Wyllie. Yates graduated and became a ship's doctor. Sadly, he caught typhus fever on his first voyage, and died at sea in 1885.

Wyllie's activity did not slacken. In 1877 he met Willie Bryden, one of the strongest players in the west of Scotland, in a subscription match and secured four wins with four draws. In 1880 came another encounter with Martins. Played at Glasgow, this was the famous match staged to settle the controversy whether 29-25 in the "Switcher" game was a losing move or could draw. The two masters were engaged to test the move and the match created much public interest. Wyllie demonstrated that 29-25 was sound and won by four games to one, with 13 draws. In 1881 he began a second American tour. It lasted four years and was again successful. By his own calculation he played 11,000 games, of which he won 10,000, lost 102, and drew 900. He twice defeated JP Reed, of Pittsburgh. His hardest test was against Charles Barker, younger brother of WR Barker. The match was played for the world championship and ended in a draw with one win each. Returning to Britain, Wyllie made another tour of England and Scotland. A second match with Bryden was played in Glasgow in 1886 and brought Wyllie victory by four games to nil, with 16 draws. Looking for new opponents, he sailed from London in 1887, and spent more than four years touring Australia and New Zealand. Scottish emmigrants had taken draughts to their new homes and Wyllie found some serious opposition from players who had acquired their skill in Caledonia. He was given a warm welcome. It was another successful journey. In Australasia he played 12,000 games, won 11,760, lost 40, and drew 200. It was after Wyllie returned to Scotland that a match was arranged between him and 19-year-old Richard Jordan, a leading member of the Edinburgh club. This match, played in the capital in May 1892, occupies a special niche in draughts history. Jordan won 2-1 with 17 draws. He went on to become world champion in 1896 and is remembered as one of the finest players draughts has produced.

In the 1890's, a new generation of Scottish Draughts stars had risen. The Herd Laddie, now in his seventies but still vigorous, turned to James Ferrie, one of the most prominent of this company, and pressed him to play for the world title. Ferrie, aged 36, who had been born in Greenock of Irish parents, agreed and the match began in Ramshorn Hall in Ingram Street, Glasgow, in April 1894. It was scheduled to be longer than any match played before, 94 games so that every possible opening could be formed in turn by each player. The end came after 88 games with Ferrie leading by 13 wins to Wyllie's six with 69 draws. So Ferrie was the new world champion. He was to have a notable career in draughts, winning the Scottish tournament six times, but he is always remembered for ending the reign of the Herd Laddie. Wyllie went on playing at the top level for five more years. He was a well-loved veteran, as was Robert Martins. The two great masters played one more match, which became known as "the last battle". Supported by subscriptions, it took place in 1897. The 52 games were split between Glasgow and Manchester. Wyllie had 10 wins to four by Martins, and there were 38 draws. Over all their encounters since 1859 Wyllie won about 12 games more than his rival. International matches between Scotland and England took place in 1884 and 1894; both were won by Scotland. A third match was arranged for April 1899, in Glasgow. Both Wyllie and Martins were chosen for the Scottish team but both were unable to play due to illness. Wyllie had been looking forward keenly to be taking part, but fell ill with bronchitis. The Scots duly completed victory against the Auld Enemy. The next morning, the sad news came that the Herd Laddie had passed on.