I would personally be surprised if Macquarie take up these 20...

I would personally be surprised if Macquarie take up these 20 cent Options, for the following reasons;

1) They have had the last 2 years to acquire shares well under 20 cents and they haven't bothered doing so

2) Their holdings have actually stayed the same in this period, although it's not easy to decipher. The group that tried the takeover is the <Metals Mining and AG A/C" which have held 14,166,667 shares since Sep 2017 (after the CR), and is the exact same holding they still retained as at 31 July 2019. Their broader Macquarie Group (inclusive of the Metals Mining & AG A/C) has previously reported higher quantities (peaking in Nov-2017 with 37.8M shares) and trickling down to their current holding as at Dec 2018. Imagine this delta is what they have traded on behalf of investors.

Unless they suddenly found religion when the Range figures were announced, they don't seem particularly interested in CTP as an investment anymore. Suspect their interest will only decrease once we re-finance our debt shortly, and word is they wouldn't mind selling their Mereenie stake too.

If they were to take up their options this is probably good and bad;

Good - Macquarie now sees CTP's market cap of $143M (20c SP) significantly increased over their previous takeover price of $87M, and they agree with the upside potential of the business from a purely share investment view

Bad - Current shareholders will be diluted ~4% for a price well below what recent Investment House research notes have advised, and CTP is not desperate for the free cash

So it will be interesting to see. I do think the 14 cent Options expiring at the end of the year look good for them, especially if the current share price is maintained or improved upon...