Summary
Updated Aug 31, 2026
Phyllis R. Caldwell is Director of JBG SMITH Properties (JBGS). 4 SEC Form 4 filings on record going back to 2025, most recently on 1 May 2026. Most recent open-market trade: bought $27K of OCSL on 18 March 2026. Lifetime open-market purchases: $67K. Historical track record: 2/5 stars across 4 tracked purchases.
Recent Transactions
5Every recent SEC Form 4 transaction Phyllis R. Caldwell has reported, most recent first.
Track Record
InsiderAlpha computes a forward-return-based score for every insider with enough Form 4 purchase history. The metrics below reflect realized performance after each tracked open-market purchase.
| Metric | Value |
|---|---|
| InsiderAlpha rating | ★★☆☆☆ (2/5) |
| Total purchases tracked | 4 |
| Purchases with forward-return data | 4 |
| 30-day win rate | 25% |
| 90-day win rate | 25% |
| Avg 5-day return | +0.73% |
| Avg 30-day return | +4.28% |
| Avg 90-day return | +0.16% |
| Best 30-day return | +18.46% |
Trading Pattern
InsiderAlpha's records for Phyllis R. Caldwell go back to 2025: 4 primary Form 4 filings, an average of 2.0 per year. The typical open-market purchase is $17K (4 buys totaling $67K). The largest single buy on record is $27K of OCSL in 2026. No transaction on record carries a Rule 10b5-1 flag - the filings look discretionary rather than pre-scheduled, which makes their timing more informative as a signal.
Other Insiders Active in the Same Stocks
Insiders who reported open-market trades in the last 12 months at the companies Phyllis R. Caldwell files at. Multiple unrelated insiders buying the same stock within a short window, cluster buying, has historically been one of the strongest Form 4 signals.
- Douglas H. Shulman - $2.08M of OMF open-market activity in the last 12 months
- Micah R. Conrad - $1.52M of OMF open-market activity in the last 12 months
- Steven A. Museles - $1.04M of JBGS open-market activity in the last 12 months
- Michael A. Hedlund - $315K of OMF open-market activity in the last 12 months
- Evan Regan-Levine - $312K of JBGS open-market activity in the last 12 months
- Scott A. Estes - $199K of JBGS open-market activity in the last 12 months
More Notable Insiders
Other corporate insiders with significant SEC Form 4 track records on InsiderAlpha:
Frequently Asked Questions
Who is Phyllis R. Caldwell?
Phyllis R. Caldwell is a corporate insider, tracked as Director of JBG SMITH Properties (JBGS). InsiderAlpha holds 4 primary Form 4 filings for them, the earliest from 2025, updated as new SEC EDGAR filings are processed.
When did Phyllis R. Caldwell last file a Form 4?
The most recent primary Form 4 on record is dated 1 May 2026, one of 4 filings going back to 2025.
Has Phyllis R. Caldwell been buying or selling stock?
Recorded transactions: 4 open-market purchases ($67K) and 0 open-market sales across all tracked filings.
How accurate is Phyllis R. Caldwell's historical track record?
Across 4 tracked purchases, Phyllis R. Caldwell averaged +4.3% avg 30-day return with a 25% 30-day win rate. InsiderAlpha rates the track record at 2/5 stars.
Where can I see all of Phyllis R. Caldwell's SEC filings?
All Form 4 filings, transaction values, and 10b5-1 plan flags are listed on this page and updated in real time as new SEC EDGAR filings are processed.
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