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Craig Jacobson Insider Profile

4 Followers
Craig Jacobson, Director at Expedia, holds 33.86K shares in Expedia (Ticker: EXPE), holds 71.67K shares in Oaktree Specialty Lending (Ticker: OCSL), holds 9.33K shares in Charter Communications (Ticker: CHTR). Most recently, Craig Jacobson Sold ― shares of Expedia on Aug 21, 2025 for an estimated value of $623.31K.
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Craig Jacobson

Craig Jacobson
Expedia (EXPE)
Director

Ranked #61,824 out of 103,431 Corporate Insiders

Profitable Transactions

56%
10 out of 18 Profitable Transactions

Average Return

-2.60%
Average return per transaction
Time Frame
1 Year
Compare to
No Benchmark

Insider Holdings

$11M
68.14%
22.72%
9.15%
A breakdown of Craig Jacobson's holdings

Insider Roles

Expedia
(EXPE)
Director
Charter Communications
(CHTR)
Director
Oaktree Specialty Lending
(OCSL)
Director
Roles that Craig Jacobson holds in companies

Most Profitable Insider Trade

Stock:
Oaktree Specialty Lending
(OCSL)
Rating:Informative Buy
Date:Mar 16, 2020 - Mar 16, 2021
Return:+80.90%
The most profitable trade made by Craig Jacobson

Craig Jacobson's Trading History

Company Name
Last Transaction Date
Insider Position
Last Transaction
Last Transaction Amount
Holding Value
Expedia
Aug 21, 2025
Director
Informative Sell
623.31K
$7.37M
OCSI
Oaktree Strategic Income Corporation
Feb 12, 2019
Informative Buy
101.03K
$348.29K
Oaktree Specialty Lending
May 07, 2025
Director
Informative Buy
199.79K
$989.72K
Charter Communications
Mar 01, 2024
Director
Informative Sell
265.51K
$2.46M
TRCO
Tribune Media Company
Sep 20, 2019
Uninformative Sell
2.02M
$0.00
List of latest transactions for each holding click on a transaction to see Craig Jacobson's performance on stock

Craig Jacobson insider profile FAQ

What is the percentage of profitable transactions made by Craig Jacobson?
The percentage of profitable transactions made by Craig Jacobson is 56%.
    What is the average return per transaction made by Craig Jacobson?
    The average return per transaction made by Craig Jacobson is -2.60%.
      What stocks does Craig Jacobson hold?
      Craig Jacobson holds: EXPE, OCSI, OCSL, CHTR, TRCO stocks.
        What was Craig Jacobson’s latest transaction?
        Craig Jacobson latest transaction was an Informative Sell of $623.31K.
          What was Craig Jacobson's most profitable transaction?
          Craig Jacobson’s most profitable transaction was an Informative Buy of OCSL stock on March 16, 2020. The return on the trade was 80.90%.
            What is Craig Jacobson's role in Expedia?
            Craig Jacobson's role in Expedia is Director.
              How can I follow the stock ratings of top corporate insiders?
              Head over to our Expert Center to see a list of the Top 100 corporate insiders and follow the corporate insiders of your choice. Visit their profiles for more details about their stock transactions and see how they perform on a stock-by-stock basis.