With the deadline to extend his contract looming, Jabari Parker’s future with the Milwaukee Bucks is clouded in risk and uncertainty.

When Jabari Parker crumpled to the ground in a heap during the third quarter of a meaningless regular season game in February, every Milwaukee Bucks fan — and every NBA fan as well — felt sick.

It’s always painful to watch a player get injured. You get that pit in your stomach and find yourself inexplicably reaching for whatever extremity the player hurt, as if you expect that your empathy somehow transmogrified your body.

In Parker’s case, though, the most painful part was the familiarity. We had all watched the exact same injury to the exact same ligament in the exact same knee two years prior.

Look how sickeningly similar the two plays are:

Bucks broadcast compares Jabari Parker's 2014 left ACL tear w/ his apparent left knee injury vs. Heat pic.twitter.com/3NK6lndXXi — Ben Golliver (@BenGolliver) February 9, 2017

As is characteristic of Parker, he’s aggressively driving. He plants hard with his left foot, and the knee just gives. Twice.

ACL injuries are not all that common in the NBA, but there is also nothing out of the ordinary about them. What is unusual is one player suffering two ACL injuries.

Unfortunately for Parker, the list of players who have suffered two ACL injuries does not inspire confidence.

After his second tear, Brent Price continued playing for a handful of years at a similar level to pre-tear. Danny Manning’s production dropped precipitously after his second. Michael Redd stuck around as a greatly diminished version of himself for a couple years after his second tear. As for Baron Davis and Josh Howard, they never played another minute of NBA basketball after their second ACL injuries.

Going forward, the Bucks have to prepare for life with, at the very least, a greatly diminished Parker. Given that he was in the midst of a true breakout season at the time of his second tear, that’s an unbelievably crushing blow to the team’s long-term prospects.

And the sucker punches to the Bucks’ future keep coming, because the front office has a major deadline looming, and a decision with immense repercussions is coming.

All players selected in the 2014 NBA Draft are eligible to receive contract extensions until Oct. 16, the day before the start of the regular season. Parker was the second overall selection in the 2014 NBA Draft, so he is among the eligible.

Undoubtedly, Parker will demand a lofty sum from the Bucks, perhaps even a maximum contract, which would total roughly $148 million over five years (depending on where exactly the cap falls in 2018).

If Parker is set on the max and will not accept a penny less, then the Bucks would be wise to walk away. But negotiations likely will not be that simple. If Parker is willing to leave a significant amount of money on the table, would the Bucks be wise to lock him up and prevent him from reaching restricted free agency next offseason?

There are, of course, various risks to locking Parker up now. Most troublingly, there’s the distinct chance that he is never the budding star we saw in 2016-17 ever again.

While it might seem that the path allowing Parker to test restricted free agency is sufficiently devoid of risk, there are numerous causes for concern.

There’s the possibility that a team with cap space is willing to offer Parker an extremely rich contract, one that the Bucks, despite having the right to match the deal, would be uncomfortable offering themselves.

The Bucks would also run the risk of fracturing their relationship with Parker, who would have the option to accept his qualifying offer, play out one more season with the Bucks in 2018-19, and leave as an unrestricted free agent in 2019.

Back in February, the Bucks’ future shimmered. Giannis Antetokounmpo was Batman and Jabari Robin. The path ahead was clear. Giannis was already extended, and Parker was set to ink a similar pact. Then Parker crumpled into a heap, just like he had two years prior.

The Bucks are now left with the tall task of minimizing risk. Unless Parker is willing to sacrifice a considerable amount of potential earnings, the Bucks will spend the next year mired in uncertainty. So, while the future will be bright as long as Giannis calls Milwaukee home, it’s gotten several magnitudes murkier since that fateful night in February.