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 | |
|---|---|---|---|---|---|---|
|
XIFR
2026
CALL
XPLR Infrastructure LP
XIFR
$1.18B
| $1.86M | ﹤0.01% |
31,700
+13,300
| +72% | +$800K |
|
|
IMGN
2027
CALL
DELISTED
Immunogen Inc
IMGN
| $1.85M | ﹤0.01% |
98,300
-245,100
| -71% | -$2.89M |
|
2028
DigitalOcean
DOCN
$14.4B
| $1.85M | ﹤0.01% |
46,117
+941
| +2% | +$34.7K |
|
2029
PUT
Herc Holdings
HRI
$5.43B
| $1.85M | ﹤0.01% |
13,500
-16,200
| -55% | -$1.79M |
|
2030
TripAdvisor
TRIP
$1.59B
| $1.85M | ﹤0.01% |
+111,956
| New | +$1.9M |
|
2031
Conagra Brands
CAG
$7.07B
| $1.84M | ﹤0.01% |
54,674
-14,822
| -21% | -$535K |
|
2032
PUT
American Water Works
AWK
$26.3B
| $1.84M | ﹤0.01% |
12,900
+5,100
| +65% | +$749K |
|
2033
CALL
Yext
YEXT
$501M
| $1.83M | ﹤0.01% |
162,200
+136,000
| +519% | +$1.29M |
|
2034
CALL
ArcBest
ARCB
$3.44B
| $1.83M | ﹤0.01% |
18,500
+16,500
| +825% | +$1.47M |
|
2035
CALL
Keurig Dr Pepper
KDP
$40.4B
| $1.83M | ﹤0.01% |
58,400
+22,900
| +65% | +$752K |
|
|
RETA
2036
DELISTED
Reata Pharmaceuticals, Inc. Class A Common Stock
RETA
| $1.82M | ﹤0.01% |
17,884
+6,143
| +52% | +$581K |
|
|
FLNA
2037
CALL
Filana Therapeutics
FLNA
$43M
| $1.82M | ﹤0.01% |
74,300
-122,700
| -62% | -$2.96M |
|
2038
United Parks & Resorts
PRKS
$2.11B
| $1.82M | ﹤0.01% |
32,508
+25,177
| +343% | +$1.42M |
|
2039
PUT
Sempra
SRE
$60.8B
| $1.82M | ﹤0.01% |
25,000
-7,600
| -23% | -$571K |
|
2040
Invesco S&P 500 Low Volatility ETF
SPLV
$7.2B
| $1.82M | ﹤0.01% |
28,926
+6,642
| +30% | +$416K |
|
2041
CALL
Alight
ALIT
$497M
| $1.81M | ﹤0.01% |
9,805
-1,010
| -9% | -$179K |
|
2042
PUT
Hess Midstream
HESM
$5.22B
| $1.81M | ﹤0.01% |
59,000
+38,700
| +191% | +$1.12M |
|
2043
CALL
Legend Biotech
LEGN
$4.3B
| $1.81M | ﹤0.01% |
26,200
-3,800
| -13% | -$248K |
|
2044
PUT
Coty
COTY
$2.33B
| $1.8M | ﹤0.01% |
146,900
+68,000
| +86% | +$803K |
|
2045
CALL
Brown & Brown
BRO
$22.9B
| $1.8M | ﹤0.01% |
26,200
+25,700
| +5,140% | +$1.63M |
|
2046
CALL
Ultragenyx Pharmaceutical
RARE
$2.65B
| $1.8M | ﹤0.01% |
39,100
+18,400
| +89% | +$853K |
|
|
CIR
2047
DELISTED
CIRCOR International, Inc
CIR
| $1.8M | ﹤0.01% |
+31,931
| New | +$1.12M |
|
2048
PUT
Orion
OEC
$394M
| $1.8M | ﹤0.01% |
84,700
-76,300
| -47% | -$1.84M |
|
2049
CALL
Lemonade
LMND
$4.62B
| $1.8M | ﹤0.01% |
106,600
-47,000
| -31% | -$735K |
|
2050
CALL
McCormick & Company Non-Voting
MKC
$13.4B
| $1.8M | ﹤0.01% |
20,600
-2,600
| -11% | -$230K |
|
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.