Certainly that describes the fund's portfolio now. Looking at its performance graph (e.g. in the latest [Dec 20
18]
annual report), one can see it diverge sharply from the S&P 500 starting around 20
12-20
13. It also significantly underperformed its category starting around 20
12, with the exception of 20
16.
The fund has been investing in Consolidated Tomoka since 2006. Going along with your comment about Berkowitz, Wintergreen held a significant portion of Consolidated Tomoka (over 5%) since day one. But it didn't represent an excessively large portion of the fund until the last 2-3 years. So while this stock holding does help explain more recent problems (thanks!), there's more to the story than one stock and a manager's obsession with it.
At the
end of 2013 CTO represented about 2.6% of Wintergreen. The fund's top holdings were Jardines (7%), Swatch (7%), and Berkshire Hathaway, with a good amount of tobacco thrown in (BAT and Reynolds, over
10% combined).
At the
end of 2014, tobacco moved up, with Reynolds in top spot (7.3%) but also BAT (6.8%) and Altria (4.7%). Consolidated Tomoka appears in the top ten at 4.7%, primarily through appreciation (50%+) but also because of some AUM shrinkage (
15%). The fund continued to hold the same number of shares as it had since 20
12; they represented 2
1% of CTO. (The 20
14 annual report has a discussion of this holding.)
By the
end of 2015, Consolidated Tomoka had grown enough to have become the fund's second largest holding (9.3%). Again, with no additional stock purchases, and with tobacco still the dominant holding - Reynolds (
12.4%), BAT (8.5%), Altria (6.3%). CTO's performance (down around 6%) was in line with the fund's 20
15 performance (down7%). The rise to 2nd largest holding was thus due to the fact that people were pulling money out of the fund and Winters didn't sell off CTO pro-rata. AUM dropped over 50%.
So arguably it wasn't until 20
16 that CTO began to dominate the fund. But Winters also continued favoring tobacco during this period. By the
end of 2016, CTO constituted
13.9% of the fund, while tobacco kept pace, with Reynolds now at
19.5%, BAT at 9.4%, and Altria at 7%. Tobacco stocks now accounted for three of the four largest holdings. CTO was essentially flat on the year, while the fund itself performed well relative to its peers, gaining 6.67%.
Once again, the increased fraction of the fund that CTO represented was a result of people pulling money out of the fund (AUM down nearly
1/3) and Winters hanging on to CTO, and onto the tobacco stocks. Note also that real estate didn't grow much as a fraction of the fund in 20
16 (just to
13.9% up from
13.5%), because Winters gave up on his other real estate holding, Sun Hung Kai.
By the
end of 2017, CTO was the fund's largest holding, at 20.4%. BAT (
now owning Reynolds) was
16.
1%, and Altria 5.7%. That was a result of CTO appreciating 20% and AUM shrinking 20%. Again, no change in the number of shares owned by the fund.
Finally, by the
end of 2018, CTO represents 42.6% of the company (despite underperforming in 20
18), BAT is still the second largest holding, but that's just 5.9% of the fund. Tobacco and every other stock have become nearly immaterial.
