In the most recent episode of All Tings Considered, Mano speaks to the difficulty of getting the right mix of reactive removal spells post-board in certain Old School matchups. The context was playing UWb midrange against a burn-heavy LDB list, but the principals can be applied to any matchup. In fact, some of the same tools you already use in deckbuilding can be utilized to come up with a coherent plan.
Sideboarding Basics (not Basic Lands)
When I've discussed sideboarding before, it was usually in the context of Modern or other current formats. The types of decks and sideboards I prefer in these formats lead me to play strong haymaker type cards that can turn bad matchups into good matchups, or punish people for getting out of line. These cards backed up with a reasonable clock form the basis for my strategy.
In Old School, these cards and strategies don't exist in the same way (one exception may be the Blood Moon Shops deck I played at Lobstercon). The haymakers are less specific and harder to utilize while still having a clock. The creatures are weaker in general. The opposing decks are more generically good and less susceptible to silver bullets.
All that means your sideboard strategy is more akin to a modern control deck. You want to upgrade your weakest cards to give you either better answers or more efficient answers while still executing the same core game plan.
Threat Diversity
For a given matchup, there will be a deck in the "beatdown" role and a deck in the "control" role. The beatdown player will want to diversify threats against the expected answers of the control player. I've spoken on this before, and I think most people have a basic understanding of this. The saying goes, "there are no wrong threats, only wrong answers". This is certainly an oversimplification, but is true enough. In the case of which one-for-one removal spells to plays, it is correct.
It's important to remember that the opponent is sideboarding as well. You may be tempted to bring in Blue Elemental Blast to answer their array of Lightning Bolts, Chain Lightnings, and other red cards. This would be a mistake if they are removing those cards post-board for non-red threats. Bringing in City in a Bottle is also tempting, but if they side out the Serendib Efreets, it can be a dead card.
Answer Diversity
Avoiding those dead cards is extremely important. Games after sideboarding generally go longer and come down to card advantage and attrition more often. However, there is a difference between a dead card and having the wrong answer and the wrong time.
A hand with Terror, Blue Elemental Blast, and Counterspell is great on an empty board. None of the cards are actively useful, but over time you will hope they line up with the threats the opponent draws. This hand gets much worse as soon as the opponent plays Mishra's Factory though. At this point, these cards stop being potential answers and instead get closer to being dead cards.
A list of possible answers you could play against a LDB deck as a UWb midrange deck:
Blue Elemental Blast (for Orcs, Blood Moon, and Bolts/Chain)
Terror (for Savannah Lions, Serendib Efreet, and Serra Angel)
Divine Offering (for Mishra's Factory and Su-Chi)
Control Magic (any non-Factory creature, but not ideal against Lion)
Healing Salve (counters Bolt/Chain and most of a Psi Blast. can win a combat)
Flash Counter (Bolt, Psiblast, Disenchant, Counterspell)
City in a Bottle (Serendib, but can get more than one)
Maze of Ith (answers all creatures but susceptible to Armageddon and burn spells)
Swords to Plowshares (does everything! its the best! you heard it here today!)
I'm sure there are others, but these were the ones I considered when building my deck for the recent event.
Counting Mana Sources
One strategy for developing a sideboard is the Elephant Method. For this, you come up with a post-board configuration for all the matchups and then add the totals to see how many cards you want. Usually this will be in the 85-90 card range. Then you have to trim down based on expected metagame and concessions for overlapping cards.
This is a lot of work.
On the other end of the spectrum, you can just throw a bunch of sideboard looking cards until you hit fifteen and go from there. You might end up with unplayable Karma in your deck this way.
I've recently treated sideboards much like building mana bases. When building a mana base, I'll have an idea for how many sources of a certain color I want to include. The Frank Karsten articles on the internet provide a good reference, but generally don't apply to Old School because the mana is so bad. Still, I may want 13 blue sources and 11 white sources and 7 black sources, but only 26 sources total, so that leads me to playing 4 Tundra, 3 Underground Sea, 1 Scrubland, 3 City of Brass, 2 Plains and 2 Island. When you know the targets for your source counts, you can fiddle with the dual land numbers until things match up.
Trying this for the LDB matchup, you may want something like 8 answers to Savannah Lions, 8 answers to Mishra's Factory, 6 answers to Serendib Efreet, 8 answers to Serra Angel, and 6 answers to Lightning Bolt. These numbers are not quite as clearly defined as the number of mana sources needed, but you should look at your totals for the post-board configuration. If it's showing 12 answers for Savannah Lions but only 6 answers for Mishra's Factory, you may be weaker to Factory than you thought.
Going back to the lists of answers to put them in context of dual lands:
Blue Elemental Blast (Bolt/Chain dual land)
Terror (Lion/Dib/Serra dual land)
Divine Offering (Factory/Su-Chi dual land, sometimes Bolt)
Control Magic (Serendib / Serra dual land)
Healing Salve (Bolt/Chain/PsiBlast dual land)
Flash Counter (Bolt/Disenchant dual land)
City in a Bottle (Serendid only)
Maze of Ith (City of Brass)
Swords to Plowshares (Even better City of Brass!)
There are lots of ways to make these duals get the numbers you may want, and it depends on the number of slots you have available. If 4 Swords to Plowshares is always a give, there may be 7 additional slots. Here you can see why I ended up on multiple Maze of Ith in my sideboard. One way to configure that is:
2 Terror
2 Maze of Ith
1 City in a Bottle
2 Divine Offering
This has 8 answers to Factory, 8 for Lions, 8 for Serra, 9 for Serendib, but nothing for Lightning Bolt beyond however many Counterspells you leave in. I'll leave it as an exercise for the reader to determine what sideboard they choose to play.
Final Note on Divine Offering vs Disenchant
I'm ready to declare myself a Divine Offering skeptic. Its good against Robots and Workshops, and perfectly reasonable if you want more than the 4 Disenchant to stop Jayemdae Tome. I think incidental life gain on Su-Chi is way overrated and not worth the weakness to Control Magic. Yes, if you know 100% there are no enchantments to kill its all upside, but it's still killing a Factory for same result every time. I was happy to play 4 Disenchant even when no one was on Blood Moon or The Abyss, and with 4 Su-Chi in my own deck. Maybe its better in a burn vs burn matchup, but in the midrange deck I don't think a hedge is necessary.
Thanks for reading,
Ty
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