Breaking down the best all-in offer Chicago Bulls can make for Damian Lillard

Should the Chicago Bulls make an all-in pursuit of Damian Lillard?

For a second, let’s assume that the Portland Trail Blazers would be willing to send Damian Lillard to the Chicago Bulls, which is far from a certainty, and that a third team would arise to help facilitate a deal similar to the one we just blue-printed out. If all those pieces fall into place, is this a worthy gamble for the Bulls?

Should the Bulls be willing to put all their poker chips in the middle of the table to go all-in for Lillard? I’m not the Bulls’ general manager and I’m not sure what pressure he’s operating under, but I’d lean no. I don’t believe this is a worthy pursuit for the Bulls.

In the end, I simply believe that the risk outweighs the possible reward. What are the risks? Well, maybe Lillard doesn’t want to play in Chicago. What if he plays for a year or half a year and then demands a trade? What if the Bulls miss the playoffs or are essentially what the Blazers have been the last few seasons and Lillard says he doesn’t want any part of it anymore?

The Bulls essentially burned all their assets for a palyer that may not be completely sold on playing for Chicago for the next four years. On the other end of the spectrum, even in a best-case scenario, the Bulls are the fourth or fifth-best team in the East?

Chicago absolutely needs to shake up their roster, but I’m simply not sure an all-in pursuit of Lillard is the right path forward.