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 | |
|---|---|---|---|---|---|---|
951
PUT
Waste Management
WM
$95.3B
| $9.04M | 0.01% |
52,100
-145,200
| -74% | -$24M |
|
952
CALL
EPAM Systems
EPAM
$4.5B
| $9.03M | 0.01% |
40,200
+19,500
| +94% | +$4.91M |
|
953
PUT
STMicroelectronics
STM
$47.7B
| $8.97M | 0.01% |
179,500
-25,400
| -12% | -$1.18M |
|
954
PUT
JB Hunt Transport Services
JBHT
$27.2B
| $8.96M | 0.01% |
49,500
+1,900
| +4% | +$331K |
|
955
PUT
Williams-Sonoma
WSM
$25.7B
| $8.95M | 0.01% |
143,000
-133,400
| -48% | -$7.95M |
|
956
PUT
Chubb
CB
$137B
| $8.93M | 0.01% |
46,400
+5,500
| +13% | +$1.08M |
|
957
CALL
Madrigal Pharmaceuticals
MDGL
$12.5B
| $8.92M | 0.01% |
38,600
-4,000
| -9% | -$1.08M |
|
958
Check Point Software Technologies
CHKP
$13.1B
| $8.91M | 0.01% |
+70,920
| New | +$8.93M |
|
|
MMP
959
PUT
DELISTED
Magellan Midstream Partners, L.P.
MMP
| $8.89M | 0.01% |
142,700
+16,100
| +13% | +$940K |
|
960
PUT
Illinois Tool Works
ITW
$79.7B
| $8.88M | 0.01% |
35,500
+24,300
| +217% | +$5.69M |
|
961
CALL
Gold Fields
GFI
$28.9B
| $8.85M | 0.01% |
640,100
+163,700
| +34% | +$2.49M |
|
962
Delta Air Lines
DAL
$53.9B
| $8.85M | 0.01% |
186,119
-195,275
| -51% | -$7.2M |
|
963
CALL
Sherwin-Williams
SHW
$76.6B
| $8.84M | 0.01% |
33,300
-10,700
| -24% | -$2.52M |
|
964
CALL
Robinhood
HOOD
$91.2B
| $8.84M | 0.01% |
885,800
-166,200
| -16% | -$1.55M |
|
965
CALL
Lennox International
LII
$18.7B
| $8.84M | 0.01% |
+27,100
| New | +$7.66M |
|
966
CALL
Prologis
PLD
$135B
| $8.83M | 0.01% |
72,000
+46,600
| +183% | +$5.73M |
|
967
CALL
Toll Brothers
TOL
$13.7B
| $8.81M | 0.01% |
111,400
+3,100
| +3% | +$208K |
|
|
VMW
968
PUT
DELISTED
VMware, Inc
VMW
| $8.81M | 0.01% |
61,300
-38,600
| -39% | -$5.01M |
|
969
CALL
Paychex
PAYX
$39.4B
| $8.76M | 0.01% |
78,300
-27,200
| -26% | -$2.97M |
|
970
CALL
AngloGold Ashanti
AU
$39.7B
| $8.76M | 0.01% |
415,300
+224,600
| +118% | +$5.66M |
|
971
PUT
Applovin
APP
$134B
| $8.73M | 0.01% |
339,500
+8,300
| +3% | +$171K |
|
972
PUT
Canadian Natural Resources
CNQ
$98B
| $8.72M | 0.01% |
310,200
-172,200
| -36% | -$4.92M |
|
|
FYBR
973
PUT
DELISTED
Frontier Communications
FYBR
| $8.72M | 0.01% |
468,000
+34,900
| +8% | +$655K |
|
974
CALL
Iron Mountain
IRM
$37.1B
| $8.72M | 0.01% |
153,400
-11,700
| -7% | -$640K |
|
975
Snap
SNAP
$7.42B
| $8.71M | 0.01% |
+735,741
| New | +$7.39M |
|
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.