Great Pirate Paint Off Painting Contest – Update #6

The Great Pirate Paint Off event has moved to the next stage! We’re a little behind on our intended timeline, but the event moves on to People’s Choice voting on May 22nd.

Check the bottom of this article for a detailed timeline for the conclusion of this event.

This last week of entries was crazy! Over the course of the first 12 weeks, we were getting about 20 entries a week. We went into the last week with about 190 entries logged. In the last week alone, we received over 220 entries! Apparently everyone is a procrastinator! I intended to keep with entries and have voting up a day or two after the contest closed, but the sheer amount of time it takes to log 220 entries and manage all those images took up an entire week! So we apologize for the delay, but it’s YOUR fault for waiting until the last minute. But we’re thrilled to have had more than 400 entries in this contest this year!

The master contest gallery has been updated. If you entered, please check that gallery to make sure all your photos made it. We had some issues with some images slipping through the cracks and we don’t want to leave any out!

(Note: in the interest of some level of anonymity for the final voting later in the Spring, we are not including painters’ names on photos going forward, except in the case of various prizes awarded during the contest.)


Well, I already spoiled the numbers here. Going into the last week we had 200 entries. By the end of the week we had a few more than 400 entries! There were many new entrants that had not submitted anything before the final week. All told, 101 painters participated in the event.

Just for a sense of scale, it can take 2-5 minutes to process an entry. Multiply 3 minutes by 200 and that’s a lot of time dragging and naming image files!

Oak and Iron had an especially impressive last week, going from 6 entries to 45.

Types of Entries

There are several different categories to enter in this contest. Right now the Unit and Commander categories have the most entries while the Oak & Iron and Force categories are pretty light so far!

  • 138 Units
  • 90 Commanders
  • 45 Oak & Iron Ships
  • 38 Ships
  • 36 Characters
  • 32 Terrain
  • 26 Forces

Oak and Iron moved from last place to 3rd, Ships stayed in 3rd place, and Characters moved from 3rd to 5th.

Terrain also got a big boost!

The Character category got a good turnout as well, including this casualty marker that is in the act of getting casualtied.

Nations Represented

The national rivalry that is part of the Summer of Plunder starts now! The Pirates maintained the lead, and the sneaky English pulled into second place, knocking out the Spanish.

  • 84 Pirate
  • 66 English
  • 45 Spanish
  • 36 French
  • 30 Unaligned
  • 21 Dutch
  • 16 Native American

The Natives were last, but they jumped from 3 to 16 in the final week so that felt like a win!

Random Prize Winner

This week the Random Prize had to be drawn from a pool of 204 entries! Holly Hayden was drawn with here entry of French Marins.

Holly will receive a little “mid contest prize” of a restrike of a 1731 Spanish 8 Reale coin. The French entries more than double in this last week and that was in no small part to Holly’s 14 entries

We’ll be doing one more random giveaway of another Fortune Coin to one of the entries submitted this next coming week.

Contest Sponsor Spotlight – Timber & Sail

In every update, we’d like to highlight one of the contest’s sponsors. This week we’d like to draw your attention to the Timber and Sail blog.

Timber & Sail is the community premier online source for all things Oak & Iron. Jason Klotz started the blog in 20XX and ha kept it up, publishing strategy guides, ship reviews, new scenarios, game news, and galleries of painted miniatures. It’s really a great resource and has become THE online source for all things Oak & Iron.

Jason from Timber & Sail has recently joined the Blood & Pigment crew and is helping manage the 2023 Summer of Plunder event. With lots of community leadership experience and technical savvy, Jason from Timber & Sail is a huge boon to both the Blood & Plunder and Oak & Iron communities.

Jason from Timber & Sail was 2023 Adepticon and ran all the Oak & Iron events, including the tournament and historical scenarios with lavish boards and some fun custom content.

L to R: Tyler (from Dead Man’s Chest), Garrett S, Dexter (from The Plunder Den), Jason (from Timber & Sail and Pigment), and Joseph F (from Blood & Pigment) at Adepticon 2023

Thanks to Timber & Sail for tirelessly supporting the Oak & Iron branch of Firelock Games. If you have been interested in Oak & Iron, check out! And if you enjoy the Summer of Plunder event and the content on Blood & Pigment, you can thank Jason for all his hard work!

For the Great Pirate Paint Off, Jason is donating an Oak & Iron expansion box for the People’s Choice Oak & Iron Ship Winner, and some awesome 3D Wake Tokens to random Oak & Iron entries.

Conclusion and Final Contest Timeline

The window for entries has closed for the 2023 Great Pirate Paint Off but the contest is still ongoing! All entries have been logged now plunder will start to flow! The categories and prize structure is a little complex for this event, so let me break it down in a quick timeline.

May 22 – Public Voting begins for People’s Choice Categories

Anyone can vote in this contest. You can vote for one entry in each category once per day. Entries are (semi) anonymous but you are welcome to share the voting page (will be posted May 22nd) far and wide with friends, family, games and anyone. Part of the goal of this contest is to share these cool miniatures, this fun game, and the talent of this awesome community with more people and get more eyeballs on it!

We limited the People’s Choice voting to a top 10 (or up to 13 in some categories) to keep voting fun and manageable. These finalists were chosen by us here at Blood & Pigment. It is always hard making cuts like that but we couldn’t really have a public voting with categories with 100+ entries.

May 29 – All non-people’s choice prizes will be awarded in Update #7
These prizes include categories for:

  • Most entries
  • Best New Painter
  • Best Kitbashed Entry
  • Plunder Den Terrain Challenge
  • Top entry from each nationality, chosen by our Summer of Plunder Commanders
  • A variety of random winners

June 4th – Voting will close for People’s Choice categories

June 5th – People’s Choice Winners will be announcedSUMMER OF PLUNDER BEGINS!
Categories include:

  • Ships
  • Commanders
  • Characters
  • Units
  • Army Forces
  • Oak & Iron
  • Terrain
  • Grand Prize – entry with the absolute largest number of votes from all categories.

Here are the new entries from the last week of the contest. It’s a full half off all the entries so it’s a big gallery! If you want to see all the entries so far, check out the complete gallery.

Update by Joseph Forster

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