My only thing with waiting those 3 weeks is i think its useless for a player with bryant potential. .
If he becomes what we and the cubs hope , wouldn't they be looking to extend him anyways by yr 3 or 4. . So what the difference if he has 6 or 7 yrs of control if he good enough to get extended. ..
Several million dollars is what it's worth. This is the argument people don't understand. That first contract you negotiate is based on what you can get in arbitration instead. For example, the way they structure contracts is such that any pre-arb years are bought out around the $500k amount though teams will often make this more of an average to make the later years cheaper. Arbitration years scale obviously since it scales as you get farther into it. So, if you end up a super-2 player and especially a good one like you hope Bryant is you're talking $5-10 mil over the life of the 7 years of team control a team has. Several million dollars is an additional player you can add in FA that might get you over the top.
Take a look at the way Mike Trout's recent contract was structured(non-super 2)
2015: $5.25 million
2016: $15.25 million
2017: $19.25 million
2018: $33.25 million
2019: $33.25 million
2020: $33.25 million
2015-2017 would have been arb1-3 for Trout. Notice how it scales compared to 18-20(essentially FA years). If he were a super 2 player 2015 would have been closer to $15 mil. Additionally, 2016 and 17 are likely more expensive given he would earn more in arbitration over 4 years rather than 3. Obviously Trout is your worst case scenario in terms of financial impact. But the point I'm making here is 3 weeks can drastically change the way a contract is structured even if you plan to extend someone.
Additionally, you have to look at this from a value stand point. I don't know whether you buy into the concept of WAR but humor me for a moment. A really good player is worth 5 WAR over the length of a season. So, how many games does Bryant actually change for you in 3 weeks? Maybe 1 tops? Unless he's on a Soriano like tear one player has relatively little impact over individual games or for that matter a dozen games. That's especially true if you're also not amazing defensively.