For this exercise, let's say Justin Upton would be able to get a contract that runs through his age-36 season if he opts for free agency. We will look at what I think Upton and his agent will target and what I think is realistic. Upton's opt-out comes at a perfect time for him since the new Qualifying Offer rules go into effect and the Tigers cannot pin one on him. That could be balanced out with the new, stiffer luxury tax penalties that may remove some teams from getting into the bidding wars this winter. It could decrease the dollar amounts teams are willing to offer even if they do jump into the fray.
There are a few different ways I can see this playing out:
Upton keeps the current deal, then gets a three-year contract
As you all probably know, Upton has four years and $88.5 million left on his contract. What kind of three-year. deal could he get in 2022? At age 34, he should be both an offensive and defensive producer or at least not a major liability in the field. It is not unrealistic to think he could get three years and $60 million like Edwin Encarnacion did this winter. That could be close to what a Qualifying Offer demands in '22. Let's say he "settles" on $18 million per year to get a three-year deal. That is $88.5 million on the current deal and $54 million on his final deal, ending in 2024. That's $142.5 million total. His only gamble is to stay healthy and productive for the next four years.
Upton opts out and signs a six-year deal, then signs a one-year deal
The best security he could look for is a six-year deal, ending in 2023. Then at 36, he would be hard pressed to get anything more than one-year deal. As the second-best bat on the market this winter (behind J.D. Martinez), he could target a contract in the $120-126 million range. Six years seems to be pushing the limit a team will swallow.
Yoenis Cespedes, the best bat on the market last winter, could not get a six-year deal. No one would get into a bidding war with the Mets, who also balked at a long contract. He re-signed for four years and $110 million with a full no-trade clause. Six years, while a good goal, may be a pipe dream. Upton may need to settle for $108-114 million total to guarantee that sixth year. In order to equal the scenario described above, he would need to get at least $22.5 million in his final one-year contract.
Jose Bautista at 36 years old got $18.5 million plus a $17 million mutual option, followed by a $20 million vesting option. So only a one year guarantee. My guess would be Upton gets a Qualifying Offer at age 36, which could be in the $20-22 million range by then. The silver lining with this route is he gains another $20-30 million guaranteed, if money is the major goal.
Upton opts out and signs a five-year deal, then signs a two-year deal
If the push for a six-year contract fails, he will have to settle for five years, then get a two-year deal at age 35. The market was not kind to power hitters last winter but most were older than 30 with limited tools. Producing career numbers in 2017, he could demand a higher AAV in a five-year deal. He shoots for $115-120 million. Let's say he lands a $115 million deal. He then only needs to average $14 million in his final two seasons to exceed the first option. Even if he only gets a $105 million deal, a two-year, $38 million follow-up deal seems very obtainable.
Upton opts out and signs a four-year deal, then signs a three-year deal
This could happen for only three reasons: Upton and his agent completely overestimate the market's willingness to enter longer term contracts (like Cespedes last year), there are only two or three teams he wants to target, or he likes the idea of re-entering the market at 34 years old rather than 35-36.
Several teams may jump at the chance to land Upton for four years while not giving up prospects. A $100-110 million deal seems like a possible goal. If they overestimate the market, he may be forced to scramble for the $88.5 million he has now. Mark Trumbo led the AL in home runs in 2016, and turned 31 years old in January. He was seeking an $80 million deal and had to settle for three years and only $37.5 million. To be fair, Trumbo is really a DH-only level player. Upton has the numbers where I can't see teams balking at a $90-100 million deal. Then he is just a three-year, $52.5 million deal away from his current situation, and playing for a solid contender.
Wild Card Mulligan
It is my understanding Upton has to make his decision right after the World Series. If his decision to stay is followed by some major personnel moves this winter, he may regret that decision. He can request a trade and has some veto power over where he is willing to go. That "ace in the hole" may go a long way to making his decision a lot less agonizing.
It could also turn into a bonanza for the Tigers as Upton has a lot of value with his contract only lasting four more years and production levels at a career high. Only J.D. Martinez is ranked above him as the best bat on the market. Whatever J.D. signs for will give the Tigers a measuring stick of what they can expect in a return for Upton if it comes to that.
I will improvise since we can't add a poll. If you wish to, use your comments to weigh in one these options :
1. He opts out and signs a six-year deal
2. He opts out and signs a five-year deal
3. He opts out and signs a four-year deal with his #1-3 target team
4. He opts out, the market stalls, and he has to settle for the same or less than his current deal
5. He stays and helps the Tigers the next four years
6. He stays, the Tigers have a fire sale, and he requests to be traded out
7. He stays, the Tigers stand pat but trade Upton anyway