Ownership history in Chesapeake Wealth Management Β· 32 quarters on record
This page tracks every 13F SEC filing in which Chesapeake Wealth Management reported a position in MICROSOFT CORP (MSFT). Data includes quarterly share count, position size as % of portfolio, estimated market value, and end-of-quarter stock price β sourced directly from SEC EDGAR 13F filings.
π Chesapeake Wealth Management outperformed the S&P 500 by +2.2% annually on this MSFT position. Timing score: 40% (12/30 decisions correct). Average cost basis: $221.50. Maximum drawdown during holding period: β30.3%.
β
Outperformed SPY on this position by 2.2% ann.
11 quarters analyzed
β οΈ Poor timing β buys often preceded drops, trims preceded rallies.
12 of 30 add/trim decisions correct
Best entry: $131.26 (2019 Q3) Β· Worst: $482.52 (2025 Q4)
πͺ Held through 1 major drawdown (>20%). Strong conviction under pressure.
7 adds Β· 25 trims. Bought during 1 of 9 down-price quarters. π Predominantly trimming β distribution phase.
π Chesapeake Wealth Management has been actively increasing its MSFT allocation β a bullish signal from insiders.
Currently 4.09% of portfolio
β Based on quarterly 13F SEC filings and end-of-quarter closing prices. Timing score = accuracy of add/trim decisions vs next-quarter price direction. Alpha = mean quarterly excess return Γ 4 (annualised). Not investment advice.
As of 2025 Q4 β sorted by position size