There were two Princes in the Tower, though, not one. What happened to Richard, Duke of York?

Holbein also painted a gentleman called Sir Henry Gylford, who conventional history says was the brother of Sir Edward Gylford, who we now know was King Edward V.

Hans Holbein the Younger 'Sir Henry Guildford' 1527

Hans Holbein the Younger ‘Sir Henry Guildford’ 1527

Henry progressed well at court, becoming Henry VIII’s Comptroller of the Household in 1522, and it is recorded that he was the half brother of Sir Edward. I just assumed that this meant that after escaping the Tower, Edward was assimilated into the Gylford family, staying abroad for a few years until he no longer looked like the young Prince people had known at Court, and long enough for stories to be told about him so his appearance back in England would not be a surprise. Suddenly coming up with a new and hitherto unmentioned teenager would have aroused questions for his surrogate father, after all.

But I was wrong. Look at the pendant on the collar of the Order of the Garter he is wearing. It is St George, slaying a dragon.

Holbein 'Sir Henry Guildford' Detail of St George and the Dragon

Holbein ‘Sir Henry Guildford’ Detail of St George and the Dragon

But this is no ordinary dragon… it is marked ‘R3’, with the rather splendid ‘R’ inset with a tny ‘R’ in place of the hole in the upper loop. Rather taken aback, I looked for the name of St George, expecting to find ‘Henry VII’, but what I found instead were the letters ‘TAGENET’. And before that, requiring a little more anxious searching and imagination… ‘PLAN’.

Holbein 'Sir Henry Guildford' detail of St George: first mention of Plantagenet

Holbein ‘Sir Henry Guildford’ detail of St George: first mention of Plantagenet

Alarmed, I thought, well it must say Henry VII on the St George himself, because he’s the person who won at Bosworth. And so I looked on the figure. The figure was indeed made up of letters, but they spelt something quite different:

Holbein 'Sir Henry Guildford' detail - second 'Plantagenet'

Holbein ‘Sir Henry Guildford’ detail – second ‘Plantagenet’

Now thoroughly disconcerted, I looked at the man’s ring, and it said ‘R’. Not ‘H’ for ‘Henry’, but ‘R’.

Holbein 'Sir Henry Guildford' detail of ring on his left hand

Holbein ‘Sir Henry Guildford’ detail of ring on his left hand

And then I saw a huge ‘R’ in front of Sir Henry’s face, and a ’73’ – the year of Richard’s birth – on it. I had missed the obvious.

Holbein 'Sir Henry Guildford' detail of face

Holbein ‘Sir Henry Guildford’ detail of face

Still not really believing it, I looked at the note pinned to the wall with sealing wax, top left, and there, much as the note on Sir Edward Godsalve’s portrait had said ‘Edward’… this one said ‘Richard’.

Holbein 'Sir Henry Guildford' detail of note top left. Letters are there, but VERY faint

Holbein ‘Sir Henry Guildford’ detail of note top left. Letters are there, but VERY faint

I had jumped to a false conclusion. Sir Henry Gylford was not a fake brother but a real one. And sure enough, when I looked into the faint brushwork of the background around Sir Henry’s head, it said ‘Richard of York’.

Holbein 'Sir Henry Guildford' detail of head

Holbein ‘Sir Henry Guildford’ detail of head. Letter very very faint, but there.

Signed, sealed and delivered, I thought.

Holbein 'Sir Henry Guildford' detail of Order of Garter Roses

Holbein ‘Sir Henry Guildford’ detail of Order of Garter Roses

And then I saw the roses.The roses in the collar of the Order of the Garter. The red roses. The Roses of Lancaster. Henry VII had changed these to Tudor roses, red and white. Was I to believe that Henry VIII, by 1527 had dropped his Tudor rose and replaced it with a Lancastrian one? And that the Yorkist Duke of York was wearing Lancastrian roses? And calling himself ‘Henry’ after the last Lancastrian King?

[To be continued…]