Simplex Trading Portfolio holdings
Simplex Trading, founded in 2004 and headquartered in Chicago, Illinois, is a technology-driven proprietary trading firm specializing in market-making and liquidity provision, primarily in U.S. equity options and futures options. Leveraging advanced proprietary software and data-driven analysis, the firm optimizes trading strategies and develops innovative solutions to capitalize on financial market opportunities, maintaining a competitive edge through automation and a collaborative team of technologists and traders. With a workforce exceeding 300 and led by CEO Erik Swanson since 2014, Simplex operates with a low-ego, high-intelligence culture, focusing on minimal bureaucracy and rapid execution, while also making strategic venture capital investments in fintech startups. Recognized as a top workplace in Chicago by Built In’s 2025 awards, Simplex continues to evolve, blending cutting-edge technology with a commitment to market efficiency and growth.
Top Buys
| Rank | Stock | Value |
|---|---|---|
| 1 |
Microsoft
MSFT
|
+$53.9M |
| 2 |
iShares 20+ Year Treasury Bond ETF
TLT
|
+$52.9M |
| 3 |
NVIDIA
NVDA
|
+$47.1M |
| 4 |
PayPal
PYPL
|
+$41.7M |
| 5 |
Alphabet (Google) Class C
GOOG
|
+$28.4M |
Top Sells
| Rank | Stock | Value |
|---|---|---|
| 1 |
Apple
AAPL
|
+$51.4M |
| 2 |
Walmart Inc
WMT
|
+$46.4M |
| 3 |
VanEck Oil Services ETF
OIH
|
+$34.2M |
| 4 |
Adobe
ADBE
|
+$33.5M |
| 5 |
Starbucks
SBUX
|
+$26.8M |
Sector Composition
| Rank | Sector | Weight |
|---|---|---|
| 1 | Technology | 0.41% |
| 2 | Healthcare | 0.21% |
| 3 | Consumer Discretionary | 0.21% |
| 4 | Communication Services | 0.2% |
| 5 | Financials | 0.15% |
| Name | Market Value | Portfolio Weight | Shares or Principal |
Change in Stake | Capital Flow | |
|---|---|---|---|---|---|---|
|
X
351
PUT
DELISTED
US Steel
X
| $35.8M | 0.03% |
1,431,900
-33,300
| -2% | -$775K |
|
352
PUT
Cigna
CI
$76.3B
| $35.8M | 0.03% |
127,600
-124,600
| -49% | -$32.4M |
|
353
CALL
Novartis
NVS
$292B
| $35.8M | 0.03% |
354,700
-38,600
| -10% | -$3.86M |
|
354
PUT
Valero Energy
VLO
$93B
| $35.8M | 0.03% |
304,800
-175,300
| -37% | -$20.4M |
|
355
CALL
DoorDash
DASH
$77.4B
| $35.6M | 0.03% |
465,400
+23,700
| +5% | +$1.57M |
|
356
PUT
Sarepta Therapeutics
SRPT
$1.69B
| $35.5M | 0.03% |
310,300
+106,000
| +52% | +$13.7M |
|
357
CALL
DraftKings
DKNG
$11.4B
| $35.3M | 0.03% |
1,327,100
+461,600
| +53% | +$10.6M |
|
358
Oracle
ORCL
$361B
| $35.2M | 0.03% |
295,783
+89,957
| +44% | +$9.3M |
|
359
CALL
Honeywell
HON
$73.6B
| $35.1M | 0.03% |
179,309
-11,883
| -6% | -$2.21M |
|
360
CALL
Upstart Holdings
UPST
$2.75B
| $35.1M | 0.03% |
979,100
-357,300
| -27% | -$8.22M |
|
361
CALL
EOG Resources
EOG
$77.3B
| $35M | 0.03% |
305,600
-88,200
| -22% | -$10.1M |
|
362
PUT
US Bancorp Series B Preferred Stock
USB.PRH
$747M
| $34.8M | 0.03% |
1,054,300
+301,700
| +40% | +$5.46M |
|
363
CALL
Autodesk
ADSK
$42.8B
| $34.8M | 0.03% |
170,200
+44,000
| +35% | +$8.8M |
|
|
DOCU
364
CALL
DocuSign
DOCU
$9.09B
| $34.7M | 0.03% |
678,900
-35,100
| -5% | -$1.86M |
|
365
CALL
Li Auto
LI
$12B
| $34.1M | 0.03% |
972,500
+82,100
| +9% | +$2.31M |
|
|
HZNP
366
PUT
DELISTED
Horizon Therapeutics Public Limited Company Ordinary Shares
HZNP
| $33.8M | 0.03% |
328,300
+271,000
| +473% | +$28.6M |
|
367
PUT
Digital Realty Trust
DLR
$66.4B
| $33.8M | 0.03% |
296,500
+58,400
| +25% | +$5.78M |
|
368
PUT
AT&T
T
$158B
| $33.8M | 0.03% |
2,406,200
-107,100
| -4% | -$1.82M |
|
|
PARA
369
CALL
DELISTED
Paramount Global Class B
PARA
| $33.7M | 0.03% |
2,121,000
+1,267,200
| +148% | +$22.9M |
|
370
CALL
Gilead Sciences
GILD
$162B
| $33.7M | 0.03% |
436,800
-100,600
| -19% | -$8.02M |
|
371
CALL
Crocs
CROX
$6.77B
| $33.5M | 0.03% |
298,100
+221,300
| +288% | +$26.4M |
|
372
CALL
Norwegian Cruise Line
NCLH
$8.93B
| $33.5M | 0.03% |
1,539,600
-340,700
| -18% | -$5.22M |
|
373
CALL
SoFi Technologies
SOFI
$21.9B
| $33.4M | 0.03% |
4,002,300
+2,746,700
| +219% | +$17.9M |
|
374
CALL
Synopsys
SNPS
$72.2B
| $33.4M | 0.03% |
76,600
+62,000
| +425% | +$25M |
|
375
CALL
Workday
WDAY
$32.9B
| $33.3M | 0.03% |
147,400
-47,300
| -24% | -$9.47M |
|
Similar funds
Simplex Trading's Q2 2023 Portfolio in Review
As of Q2 2023, Simplex Trading held 10,535 positions worth $122B, up 6.9% from $114B the previous quarter. Its ten largest holdings account for 43% of the portfolio.
Simplex Trading's Q2 2023 filing shows 1,474 new, 3,350 increased, 3,913 reduced and 1,517 closed positions. Its largest new stake was Microsoft: 171,935 shares worth $58.5M. The largest sale was Apple, an estimated $51.4M.
By sector, the portfolio is most concentrated in Technology at 0.41% of assets, down from 0.42% a quarter earlier, followed by Healthcare and Consumer Discretionary.
- Simplex Trading's largest Q2 2023 buy was Microsoft: 171,935 shares worth $58.5M.
- Simplex Trading added most to iShares 20+ Year Treasury Bond ETF in Q2 2023, an estimated $52.9M increase.
- Simplex Trading's biggest Q2 2023 reduction was Adobe, cutting an estimated $33.5M.
- Simplex Trading fully exited Apple in Q2 2023, selling an estimated $51.4M.
- Simplex Trading's ten largest holdings make up 43% of its $122B portfolio in Q2 2023.
- Simplex Trading opened 1,474 new positions and closed 1,517 in Q2 2023.
- Simplex Trading's portfolio value rose 6.9% quarter-over-quarter to $122B.
Based on Simplex Trading's 13F filing for Q2 2023, filed 4 Aug 2023.