Nefarious Trading
Deep Dive · Nefarious Trading
Vol. 01 · No. 40
May 30, 2026
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IBM $297.80 ▲ +12.7% MSFT $450.24 ▲ +5.4% IBM LEAPS Jan 2027 $290/$340 MSFT LEAPS Jan 2027 $450/$520 ACKMAN $2.1B new MSFT IBM +12.7% on 5x vol IBM TARGET $360-380 MSFT TARGET $540-580
Two LEAPS · Both Bullish
IBM + MSFT
JAN 2027 CALL SPREADS
Top Conviction
IBM 4.5/5
▲ +12.7% on 5x volume · breakout day
LEAPS · Both Bullish · Technical-Led Entries

Two LEAPS I’m bullish on. IBM is the cheap-multiple AI hybrid. MSFT is the Ackman trade.

IBM · Jan 2027 $290/$340 call spread · target $360-380 · 12-14 month hold · 4.5/5 conviction. MSFT · Jan 2027 $450/$520 call spread · target $540-580 · same horizon · 4.0/5 with the Ackman $2.1B whale anchor. Both up hard today (IBM +12.7%, MSFT +5.4%) so the trade is to set GTC limits at the retrace zones and wait. Below: technical read, entry levels, and why I’m skipping ORCL, PLTR, and PENG as LEAPS.

IBM Setup
$290/$340
Jan 2027 spread · enter on retrace to $278-285
MSFT Setup
$450/$520
Jan 2027 spread · enter on retrace to $425-435
Ackman Anchor
$2.1B
New Q1 MSFT · multi-year hold style
Timing
Don't enter today
IV expanded · wait 5-10 day consolidation
§ 01 — The Setup · Both Names Today

Two LEAPS · both bullish · both up hard today. The trade is timing, not direction.

IBM +12.7% on 28M shares (~5x avg vol). MSFT +5.4% on heavy volume. Both wide-range breakout bars on a sector-wide AI rally. Bulkowski catalogs this as a high-probability mean-reversion setup over the next 5 days · pullbacks of 5-10% statistically common post-spike. IV expanded 15-30% so LEAPS premiums are 5-15% pricier than yesterday. Net: don't enter today · set GTC limits at the retrace zones.

TickerPriceTodayP/EFCFMkt CapFrom 52W High
IBM$297.80+12.7%26.0x$13.1B$280B-8.3%
MSFT$450.24+5.4%26.7x$72.9B$3.34T-18.9%

Why Call Spreads, Not Naked Calls

IV expansion today means naked long calls carry elevated vega. Selling the higher strike against the long lower strike (call spread) reduces net vega exposure and partially offsets the IV premium you're paying. Cost goes down · max profit caps but R/R stays ~2x on both names.

§ 02 — IBM · The Cheap-Multiple AI Hybrid

The cleanest LEAPS setup. 26x P/E · 4.7% FCF yield · $13B FCF · bipartisan Congress buying.

IBM is the cheapest credible AI exposure in megacap. Watsonx + Red Hat + consulting moat · AI agent and hybrid cloud bookings accelerating. Up 40% off lows but still cheap vs the AI cohort. Today's +12.7% on 28M shares (~5x average volume) is the strongest institutional signal in the basket.

The stack: 26x P/E (vs PLTR 164x, ORCL 40x) · $13.1B FCF · Congressional buying (Khanna-D, McCaul-R, Cisneros-D, Doggett-D Apr-May) · new Swedish whale (Lansforsakringar) · 5x volume breakout day.

Technical Read

Today's Bar+12.7% on 28M shares · ~5x avg vol · wide-range breakout
Position In Range-8.3% from 52W high · +40% from low · uptrend intact
PatternBulkowski Wide Range Bar on Volume · bullish · mean-reversion likely 3-5 days
Support$280-285 (prior breakout zone) · $270 (50DMA) · $255 (deeper)
Resistance$325 (52W high) · $345-360 (Fib extension target)
Entry WindowRetrace to $278-285 · GTC limit orders this zone

The Trade

StructureJan 2027 $290/$340 call spread on pullback to $278-285
Cost~$22-26 per spread
Max Profit$50 if IBM > $340 at Jan 2027 expiry
Risk/Reward~2.0x
Target$360-380 in 12-14 months · +20-28% on stock · +80-150% on spread

Risk

After +12.7% spike you're chasing at current levels. IV expanded. Setup needs the post-spike consolidation to materialize · if IBM rips through $325 without a pullback, entry zone resets higher and R/R degrades.

§ 03 — MSFT · The Ackman Trade

The boring pick. $72.9B FCF · Pershing Square $2.1B new Q1 · 4 directors bought March 12.

Default AI infra exposure · Azure + OpenAI + Copilot + M365. The "almost impossible to lose money on over 18 months" pick. Today's +5.4% is less stretched than IBM's +12.7%, which makes entry timing more favorable.

Ackman is the trade. Pershing Square opened a NEW $2.1B position in Q1 2026. Ackman runs a concentrated 6-10 position book with multi-year holds. He doesn't trade. Conviction-level smart money at sub-$450.

Bullish Stack

  • Ackman $2.1B new Q1 · multi-year conviction
  • 4 directors bought March 12 · Walmsley, Rainey, Pritzker, Peterson
  • Citadel increased · quant accumulation
  • $72.9B FCF · strongest cash machine in megacap
  • Bipartisan Congress buying · McGuire-R, Warner-D, Boozman-R, Salazar-R

Technical Read

Today's Bar+5.4% to $450.24 · less stretched · room to run before mean reversion
Position In Range-18.9% from $555 52W high
$450 LevelPrior support reclaimed · launchpad if held
200DMA~$440-445 · key technical line · Ackman likely entered near here
Support$425-435 (entry zone) · $400 (deeper)
Resistance$480 · $500 (psychological breakout) · $555 (52W high)
SetupCup-and-handle pending if $500 breaks · target $580+

The Trade

StructureJan 2027 $450/$520 call spread on pullback to $425-435
Cost~$30-35 per spread
Max Profit$70
Risk/Reward~2.0-2.3x
Target$540-580 in 12-14 months · +20-29% upside

Why Not 5.0

-18.9% from 52W high · 26.7x P/E reasonable not cheap · Copilot monetization questions · Azure deceleration would compress multiple.

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"Two LEAPS · both bullish · IBM for cheap multiple, MSFT for the Ackman anchor. Don't pay today's IV — wait for the retrace."
§ 04 — Not LEAPS · The Other Three

Why ORCL, PLTR, PENG aren't in my LEAPS book. One line each.

TickerPriceWhy Not LEAPSIf You Want Exposure
ORCL$225.81-$24.7B trailing FCF · 14 months of premium decay against existential cash burn riskMonthly $200/$185 bull put spread · sell premium into elevated IV
PLTR$156.54164x P/E · multiple compression to 80x (still expensive) = 50% drop · LEAPS unfavorableMonthly $135 CSP · collect premium · assignment at discount
PENG$55.83Cluster insider selling (4 officers Apr 16-20) near 52W high · options illiquid at $2.9B capBuy stock directly or Jan 2027 $60c at 1% portfolio max
§ 05 — Entry Triggers · GTC Limit Orders

Set these and wait. Don't pay today's IV.

TickerTodayRetrace ToThen TriggerSpread Cost
IBM$297.80$278-285Jan 2027 $290/$340 spread~$22-26
MSFT$450.24$425-435Jan 2027 $450/$520 spread~$30-35

Post-spike pullbacks of 5-10% statistically common within 5 trading days · these GTC zones represent that retrace. If neither hits in 10 trading days, reassess against new support zones.

§ 06 — My Take

Two LEAPS · both bullish · both wait for retrace. That's the whole trade.

IBM is the cheap-multiple bet · 26x P/E + $13B FCF + bipartisan Congress accumulation + 5x-volume breakout day. MSFT is the Ackman bet · $2.1B new Q1 position is the single strongest smart-money signal in software right now. Both call spreads (not naked calls) to reduce vega · both targeting +20-29% upside on the underlying over 12-14 months · both waiting on a retrace zone before entry.

The Trade Plan

IBM LEAPS
Jan 2027 $290/$340 spread · enter $278-285 · target $360-380
MSFT LEAPS
Jan 2027 $450/$520 spread · enter $425-435 · target $540-580
CONVICTION
IBM 4.5/5 (cheapest) · MSFT 4.0/5 (Ackman anchor)
TIMING
GTC limits · don't enter today · IV expanded
STRUCTURE
Call spreads not naked · reduces vega exposure
SKIP
ORCL · PLTR · PENG (covered §04)
"Two LEAPS · both bullish · IBM for cheap multiple, MSFT for the Ackman anchor. Spreads not naked. GTC limits at retrace zones. Don't pay today's IV."
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"IBM is the cleanest LEAPS. MSFT is the Ackman trade. ORCL + PLTR are swing-only. PENG small size. GTC limits at retrace."