AP

When the Raiders got the Bears’ first-round draft pick in the Khalil Mack trade before the season, the Vegas odds had the Bears pegged as a 6-10 team. When the Raiders got the Cowboys’ first-round draft pick in the Amari Cooper trade in October, Dallas had a losing record and was a game and a half out of first place in the NFC East. At the time they made those trades, the Raiders thought they were getting two high first-round picks.

It’s not working out that way.

The Cowboys and Bears are now clear favorites to win their divisions, which would put both of their first-round draft picks outside the Top 20. A division winner’s first-round draft pick can be no higher than No. 21 overall, and in the worst-case scenario for the Raiders (and best-case scenario for the Cowboys and Bears), those picks could be as low as No. 30 and No. 32 overall.

If the Raiders had realized how good the Cowboys and Bears would be, would they still have made those trades? In the case of Cooper, they still might have: It was clear that Raiders coach Jon Gruden didn’t think Cooper was going to be a big part of his offense in the long run, and getting a first-round pick for him might have been worth it to Gruden even if that pick turns out to be No. 32 overall.

In the case of Mack, however, Gruden is probably kicking himself. The 49ers have said they made just as aggressive an offer for Mack as the Bears did, but the Raiders went with the Bears. At the time, that was reasonable: Most people thought the 49ers would be a better team than the Bears, so the 49ers’ first-round pick would be worse than the Bears’ first-round pick.

That’s not how it turned out. The 49ers are still in contention for the first overall pick, and the Bears are still in contention for the 32nd overall pick. Going with the Bears over the 49ers looks, in hindsight, like a huge mistake.

And that’s part of the risk of trading for a future first-round draft pick: The compensation might not turn out to be as good as you think it will be. The Raiders are finding that out the hard way.

There is one piece of good news for Gruden: His own team stinks. He could get the first overall pick in the draft that way, and then two late first-round picks from the Cowboys and Bears.