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Note: I don't hold any positions in OCSL.
One thing that I always find worth digging into is when someone sits on the board of a small company AND a huge one, especially when they have a dealmaking (M&A) background. Last I posted about QuantumScape and the Tesla board connection. This one is different because here the insiders are buying, not selling [Stock down by about 9.5% YTD].
OCSL (Oaktree Specialty Lending, $1B market cap) is basically a company that lends money to mid sized businesses. It's run by Oaktree Capital, Howard Marks's firm. If you don't know Marks, he wrote "The Most Important Thing" which is like the bible for value investors. Oaktree manages $223B and is one of the biggest credit shops on the planet.
Here's who sits on OCSL's board and where else they sit:
| Person | OCSL ($1B) | Other Board | Background |
|--------|-----------|-------------|------------|
| John B. Frank | Director | Chevron ($366B) | Vice Chairman of Oaktree, used to be a mergers and acquisitions partner at Charlie Munger's law firm |
| Phyllis R. Caldwell | Director | OneMain Financial ($6.7B), JBG Smith ($925M) | Worked at US Treasury under Obama running the housing bailout programs, retired Bank of America exec |
| Craig Jacobson | Director | Expedia ($24.5B) | Started his own investment bank (Whisper Advisors), was on boards during the Tribune/Nexstar and Ticketmaster/Live Nation mergers |
Three independent directors. All on multiple public company boards. All with dealmaking backgrounds.
Now here's what I found interesting. Two of these three are buying OCSL stock with their own money.
*Phyllis Caldwell has been buying all year:*
| Date | Shares | Price | Value |
|------|--------|-------|-------|
| Feb 27, 2025 | 2,500 | $15.83 | ~$40K |
| May 7, 2025 | 2,000 | $13.33 | ~$27K |
| Sep 15, 2025 | 3,000 | $13.19 | ~$40K |
Three purchases in 2025. She kept buying more as the price dropped.
*Craig Jacobson dropped $200K :*
| Date | Shares | Price | Value |
|------|--------|-------|-------|
| May 6, 2025 | 14,910 | $13.41 | ~$200K |
That bumped his holdings by 62% overnight. Meanwhile he sold $815K of Expedia stock in November near all time highs ($271/share). So he's cashing out his winner and putting money into OCSL instead.
*John B. Frank hasn't bought or sold a single share of OCSL or Chevron in over 5 years.* So total silence from the #2 guy at a $223B firm. He holds about 9,600 shares of OCSL and about 10,400 shares of Chevron.
To me this buying was interesting because OCSL trades at about $12.21 per share right now. But if you add up everything the company actually owns minus what it owes, each share is worth about $16.30. That's a 25% discount. Think of it like a house appraised at $163K selling for $122K. The people who sit in the boardroom and can see exactly what the company owns think it's worth paying $13+ when the market says $12. Board members don't usually drop $200K on a stock they think is fairly priced.
Oh and the business itself is doing fine. OCSL just reported earnings on Feb 4 and beat expectations. They made $0.41 per share vs the $0.38 Wall Street expected. So this isn't a case of insiders buying a sinking ship. The company is performing and the stock is still cheap based off the data.
Now for the bigger picture.
Brookfield (giant Canadian asset manager) is buying the remaining 26% of Oaktree Capital for $3B. Expected to close first half of 2026. When that's done, Brookfield will own 100% of Oaktree and everything it manages, including OCSL.
This matters because Brookfield has a track record of cleaning house after acquisitions. They like to merge smaller funds together into bigger ones. OCSL already absorbed another Oaktree fund (Oaktree Strategic Income II) back in January 2023. More mergers are very much on the table.
Something else worth noting. OCSL recently held a special shareholder vote to let them issue new stock below book value. And in Feb 2025, Oaktree itself bought $100M of brand new OCSL stock at $17.63 per share. The parent company is putting its own money in at a much higher price than where the stock trades today.
If Brookfield decides to take OCSL private or fold it into a bigger fund after the acquisition closes, they'd probably have to pay close to what the shares are actually worth (that $16.30 number). That's 25 to 33% above where it trades right now.
About Frank specifically. This guy was a mergers partner at Charlie Munger's law firm. Then he spent 20+ years at Oaktree climbing to Vice Chairman. He took Oaktree public. He helped negotiate the Brookfield deal. He was on Chevron's board when they bought Hess for $53B last year. This person has been in the room for some of the biggest deals of the last decade.
And he's not selling a single share of OCSL. Two out of three directors with seats on big company boards are buying with their own cash, the parent company put in $100M, and there's a real catalyst (Brookfield closing the deal) coming within months.
What I'm watching for:
Any SEC filing that signals a going private deal
OCSL announcing they're "reviewing strategic alternatives" (corporate speak for "we might sell")
Changes to how Oaktree charges fees after Brookfield takes full ownership
Frank breaking his 5 year silence and buying or selling
More director purchases at these prices
OCSL's next earnings call for any change in tone about the Brookfield transition
I'm not saying a deal is definitely happening. I'm saying all the ingredients are there.