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 | Miscellaneous | 98.43% |
| 2 | Technology | 0.41% |
| 3 | Healthcare | 0.21% |
| 4 | Consumer Discretionary | 0.21% |
| 5 | Communication Services | 0.21% |
| Name | Market Value | Portfolio Weight | Shares or Principal |
Change in Stake | Capital Flow | Held Since | |
|---|---|---|---|---|---|---|---|
1
PUT
State Street SPDR S&P 500 ETF Trust
SPY
$815B
| $14.7B | 12.11% |
33,317,100
+3,521,600
| +12% | +$1.48B |
2015 Q1
33 quarters
|
|
|
2
CALL
State Street SPDR S&P 500 ETF Trust
SPY
$815B
| $8.51B | 6.99% |
19,208,800
+220,600
| +1% | +$92.6M |
2015 Q1
33 quarters
|
|
3
PUT
Invesco QQQ Trust
QQQ
$478B
| $5.89B | 4.84% |
15,967,800
-2,210,900
| -12% | -$744M |
2021 Q2
8 quarters
|
|
4
PUT
iShares S&P 100 ETF
OEF
$20.4B
| $3.95B | 3.24% |
30,329,700
-472,200
| -2% | -$91.8M |
2014 Q4
34 quarters
|
|
5
CALL
Tesla
TSLA
$1.5T
| $3.59B | 2.95% |
13,706,900
+1,079,700
| +9% | +$216M |
2021 Q2
8 quarters
|
|
|
6
PUT
Tesla
TSLA
$1.5T
| $3.52B | 2.89% |
13,449,100
+2,604,200
| +24% | +$521M |
2021 Q2
8 quarters
|
|
|
7
CALL
Invesco QQQ Trust
QQQ
$478B
| $3.15B | 2.59% |
8,533,800
-1,680,600
| -16% | -$566M |
2021 Q2
8 quarters
|
|
|
8
CALL
iShares S&P 100 ETF
OEF
$20.4B
| $3.14B | 2.58% |
22,658,700
+3,731,900
| +20% | +$725M |
2014 Q4
34 quarters
|
|
|
9
CALL
Apple
AAPL
$5.05T
| $2.73B | 2.24% |
14,078,300
+4,972,300
| +55% | +$866M |
2015 Q1
33 quarters
|
|
|
10
PUT
NVIDIA
NVDA
$5.15T
| $2.57B | 2.11% |
60,796,000
+12,847,000
| +27% | +$427M |
2021 Q2
8 quarters
|
|
|
11
CALL
NVIDIA
NVDA
$5.15T
| $2.41B | 1.98% |
56,925,000
+13,983,000
| +33% | +$464M |
2021 Q2
8 quarters
|
|
|
12
PUT
Apple
AAPL
$5.05T
| $2B | 1.64% |
10,294,400
+1,375,400
| +15% | +$240M |
2015 Q1
33 quarters
|
|
13
CALL
Alphabet (Google) Class A
GOOGL
$4T
| $1.53B | 1.26% |
12,738,100
-440,500
| -3% | -$50.7M |
2015 Q4
30 quarters
|
|
14
CALL
Amazon
AMZN
$2.72T
| $1.46B | 1.2% |
11,236,500
-3,303,500
| -23% | -$377M |
2015 Q1
33 quarters
|
|
15
CALL
Meta Platforms (Facebook)
META
$1.65T
| $1.45B | 1.19% |
5,058,600
-1,838,300
| -27% | -$454M |
2014 Q4
34 quarters
|
|
|
16
CALL
Microsoft
MSFT
$3.9T
| $1.35B | 1.11% |
3,961,700
-734,700
| -16% | -$230M |
2014 Q4
34 quarters
|
|
|
17
PUT
Microsoft
MSFT
$3.9T
| $1.31B | 1.08% |
3,849,100
+646,800
| +20% | +$203M |
2014 Q4
34 quarters
|
|
|
18
PUT
Alphabet (Google) Class A
GOOGL
$4T
| $1.11B | 0.92% |
9,242,000
+1,572,500
| +21% | +$181M |
2015 Q4
30 quarters
|
|
19
PUT
State Street Materials Select Sector SPDR ETF
XLB
$8.14B
| $1.06B | 0.87% |
30,619,800
-9,122,800
| -23% | -$363M |
2015 Q1
33 quarters
|
|
|
20
PUT
Meta Platforms (Facebook)
META
$1.65T
| $1.04B | 0.85% |
3,620,800
-456,900
| -11% | -$113M |
2014 Q4
34 quarters
|
|
|
21
PUT
Amazon
AMZN
$2.72T
| $952M | 0.78% |
7,299,800
+1,753,600
| +32% | +$200M |
2015 Q1
33 quarters
|
|
22
CALL
SPDR Gold Trust
GLD
$137B
| $806M | 0.66% |
4,519,800
-1,435,200
| -24% | -$264M |
2015 Q1
33 quarters
|
|
23
PUT
Netflix
NFLX
$280B
| $747M | 0.61% |
16,965,000
-4,023,000
| -19% | -$148M |
2014 Q4
34 quarters
|
|
|
24
CALL
Netflix
NFLX
$280B
| $725M | 0.6% |
16,467,000
-1,052,000
| -6% | -$38.7M |
2014 Q4
34 quarters
|
|
|
25
CALL
State Street Materials Select Sector SPDR ETF
XLB
$8.14B
| $708M | 0.58% |
19,409,600
-8,129,400
| -30% | -$323M |
2015 Q1
33 quarters
|
|
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, 3,349 increased, 3,911 reduced and 1,515 closed positions. Its largest new stake was Microsoft: 171,935 shares worth $58.6M. The largest sale was Apple, an estimated $51.4M.
By sector, the portfolio is most concentrated in Miscellaneous at 98% of assets, down from 99% a quarter earlier, followed by Technology and Healthcare.
- Simplex Trading's largest Q2 2023 buy was Microsoft: 171,935 shares worth $58.6M.
- 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 1,515 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.