2. Yoan Moncada
The third baseman is arguably more important to lock up now to ensure cost-control later on after he recorded a 5.7 fWAR with a 141 wRC+ in 2019.
While he has the same arbitration (hits it for the first time after the 2020 season) and team control (free agent after 2023 season) situation as Giolito, he’s quickly ascended into star category and hitters tend to get paid more than pitchers.
Arbitration, in particular, is very kind to position player stars like Moncada and his first-time salary next offseason could possibly be $6-$7 million.
If he were to maintain his level of production offensively last season and maybe even improve defensively (-7 DRS, 4.3 UZR in 1,095 2/3 innings), Moncada could get a salary over $20 million in his final season arbitration anyways.
Unlike Giolito, waiting a year to see if Moncada can replicate his performance could significantly alter the price of an extension in the wrong direction.
A price tag of six years, $100-$110 million to sign him long-term now and buy out a few his free agent seasons makes sense, but next offseason that could jump into the seven-year, $160-$180 million range.
Both contracts would be deemed great value if the 24-year-old is as good going forward as he was in 2019. However, the first contract extension would save the team significantly more money in the future.