DraftKings Inc. Class A Common Stock

PENN Entertainment, Inc. Common Stock

About six weeks ago, I was looking at my position in $PENN,  realizing I was more overweight than I was comfortable with, and also realizing that 10% of my shares represented like 75% of my total losses.  I wanted to buy cheaper shares (it was trading at $23 at the time) and replace those higher priced shares. Lower my overall CB, lock in the tax loss, continue the position for the long haul.

This week I was supposed to execute that strategy, free of the wash sale rules and post-earnings (I expected we were at/near a bottom).  Maybe it's not an optimal use of cash, or an optimal strategy, but I had convinced myself it was the best move for my position at the time.  Then they pulled the trigger on the deal with ESPN, and I discussed earlier this week the struggle I was facing regarding my position going forward, as a lot of my thesis was centered around a Barstool/PENN collab competing with $DKNG and FanDuel (see that writeup here: [https://commonstock.com/post/123d42c4-0b56-486c-8f7d-8d7085add0fc](https://commonstock.com/post/123d42c4-0b56-486c-8f7d-8d7085add0fc))

Ultimately, I decided it was best to stick to the strategy I laid out for myself and sold those expensive shares, lowering my overall CB and lightening my position slightly.  The surprising turn of events for me, was that I reallocated almost all of those funds into $DKNG - they were always a small piece of my portfolio, but management has seemed to be consistent in their strategy and successful, and owns a signficant piece of the sports betting landscape at this point.  The Penn/ESPN deal reeks of a little desperation on both sides (ESPN knew they needed a hand in sports betting, Penn knew they needed a better branding partner to get any sort of decent market share).

I haven't sold all of my Penn, as I like the CEO and think his strategy is right (even if he got the partner wrong the first time, and gave Barstool back for $1), but they have their own in-house betting tech stack, and now are partnered with the largest sports media company in the US and own the largest sports media company in Canada; long term, maybe they overpaid for the ESPN deal (see Iger's quote below from their earnings yesterday), but they had no choice - they were about to be just another irrelevant sportsbook.

![Image upload](https://cdn.commonstock.com/a104b43aa5e1dfd0934ce0f9c96ef3a36ff05c70512d1cd79a351145bcb3991f-1261x171.png)

If they can parlay the ESPN brand into a larger market share, and continue their road to profitability, the stock should do okay long term.  But if it pops back to $30+ in the near future, you might see me head for the exits, or at least significantly pare down - it's not one of my five best ideas, so it shouldn't be one of my five largest positions.  Stay tuned for the next update of my gambling stocks!

If I was into gambling stocks I agree with everything you’ve said to date so far regarding penn and Disney and draftlings. However I hate gambling lol. I hate giving my money to the man so I’ll never invest in those names even though I probably should. I was very skeptical of penn and barstool deal way back because of how polarizing portnoy is similar to Elon but in his own way lol. But both super super smart guys. Penn is in a really good position right now. They messed up once but I think they got it right with this new partnership 

Christian

How did you come about the $30 exit price? That's well off 52-week high of $39.35

Joshua Simka

Jared Watson

An update for my $PENN position..

Sold 11% of PENN

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