Quick summary: A contract that is difficult to make good use of, one which doesn't instantly make things easier like Bond of Friendship, but which can make non-secrecy two-hero decks viable.

Let's start with the downsides: you may only choose two heroes, meaning you get fewer resources and actions per turn, you start out unable to heal, and your heroes cannot gain resources from attachment card effects, so no using anything like Steward of Gondor or gaining resources via Gandalf's Staff.

Let's break down the two heroes. A quick glance through published decks shows that, if you're not running The Grey Wanderer, chances are the deck will have either 3 or, in the case of Bond of Friendship, 4 heroes. The threat cost is worth it when you get more starting actions and more resources each turn. Two-hero decks, which one may think would be the realm of secrecy, have been dead every since Folco Boffin was released, as you can simply include him and, at the worst, be one threat cost better if you immediately discard him, and at best can use his resource(s) and stats until you need to get back into secrecy. If you look through the number of published One Decks, decks able to take on every scenario officially released, the vast majority use Bond of Friendship, because threat is manageable and the extra actions and resources are worth the harsh deckbuilding restrictions.

So, what's the upside? It's certainly not making secrecy more viable, as each starting hero gets +4 threat cost, which is enough to push almost any two-hero combination out of secrecy. Each hero gets a +1/+1/+1/+1 stat boost, which is nice, and you get some inherent resource smoothing. You can recover a hero action by damaging one of your starting heroes to ready the other, though without healing while you're on this side of the contract you do need to be careful.

For the resource smoothing, this enables some very nice plays. If you play with a and a hero, you can select a hero with high innate , have it boosted, and now that hero is in sphere for both A Burning Brand and Armored Destrier, nullifying most shadows and taking care of defensive duties.

Is the +1/+1/+1/+1 boost worth the threat cost and loss of resources? That depends on which heroes you pick. Ideally, you want heroes with some form of built-in action advantage to make use of multiple of these stats. Radagast with 4 and 5, as well as 3 that he doesn't exhaust to quest with, is one example of a hero that uses this contract well. Additionally, the other hero you choose also gains all spheres when playing a creature ally because Radagast gets them printed at that time. Radagast can even use a Wizard Pipe, Hidden Cache, and Messenger Raven to generate resources, and his Staff to apply discounts. Sam Gamgee would be another great choice, provided you can keep your threat low enough to make use of his ability. Of course, cards like Strider or Light of Valinor are essential early cards to ensure you aren't overwhelmed before round 4.

On the fourth round, you can really start hitting back. A 2-card search from your entire deck makes a lot of decks suddenly consistent, and the 6-resource boost puts you ahead in resource terms of where a standard 3-hero deck would be without any acceleration. If your deck relies on a 2-card combo to run in the long-term, you will always be able to find it. It's this 2-card search that really makes the contract worth using at all, and you can build many 2-hero decks that work well with it. That's not to say it's as powerful as some of the official contracts, but I'm not convinced that's a bad thing. Being able to make viable Aragorn-Arwen Undómiel or Elladan-Elrohir decks without making them instantly top-tier is a win in my book.

It seems like this should have cost zero, or come with a card draw like Mighty Warrior, Fearless Scout, Diligent Noble, Song of Eärendil, or Doughty Ranger. Even those examples usually end up as binder fodder, and this is significantly worse. This matches the (awful) template of Nor am I a Stranger (Rohan) and Elf-friend (Silvan and Noldor), which similarly should have had a card draw attached or cost reduced.

If you need the Gondor trait and Steward of Gondor isn't enough, maybe consider Elessar before In Service of the Steward.

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The only remote time I can see this useful is to give the Gondor trait to an ally, perhaps for Sword of Morthond? —

This is, without question, the worst designed card in the game. At GenCon a few years ago, a player showed up for the convention exclusive event with this guy as one of his heroes. His intention was to force a game loss by driving everyone’s threat up. It was the most negative play experience I’ve ever had with this otherwise fantastic game. Doomed should have not raised other players’ threats this way.

I think this says more about that player than Grima himself. But still yeah he is more of a solo player. Unlike the Doomed events which benefit all players his Doomed will usually benefit more the Grima's player (but it can still be used to discount some global effects). —

Planning on use it for first time in LOTR Saga in The Battle of the Pelennor Fields and/or The Tower of Cirith Ungol to get ride of the Wraith on Wings.

These scenarios are one of the few cases where I find it useful enough. But even then, you still have to engage them before completing this quest, not easy.

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Even in that case I am not totally sure it's worth it. Since it's a battle side quest you need to devote a large amount of attacking power to it, attacking power that could have possibly been used to kill the Wraith the old fashioned way. Helm! Helm! or Ride Them Down (or even Hunting Party) might be better options to deal with the Wraith on Wings —
  1. Can Treebeard pay for, say, Derndingle Warrior purely out of his collected resource pool if for example my only Tactics hero was captured during Escape from Dol Guldur and thus Derndingle Warrior being out-of-sphere at that time?
  2. Does Treebeard enter play exhausted even if cheated in play with say, Sneak Attack or Elf-stone?
Correct on both points —
Treebeard resources break the need for a resource match when used to play for an Ent. And he "enters play" exhausted, so no matter if you play or put into play him —