This completely misses the point. The Cubs don't need to do one of these early multiyear deals with Soto, in part because they've been 100% successful locking up the guys they want to keep when they're on the verge of reaching free agency. Ramirez was making less than what Soto will make via the arbitration process, assuming he continues posting .900 OPSs for the next 5 years. Same with DLee. Raimrez made $3M in his first arb year, and $6M in his second, as part of a 3-year deal he signed while in Pittsburgh. Then he signed a multiyear deal with the Cubs that spanned his final arb year and his first three FA years. Lee went year-to-year, getting $2.7M, then $4.25M in arb years 1 and 2. Arb year 3 was absorbed into the 3-year deal he signed after being traded here. Soto's level of financial security will be no different than these guys' were at the time they inked longterm deals with the Cubs, again, provided he remains healthy and productive. Now he may prefer to sign an early extension that locks him in through his arb years, but the Cubs have little incentive to give it to him. Except the incentive of paying less in the long run. Paying less in the long run is only one possibility. Another possibility is that the extension guarantees higher salaries than the player would've earned if taken year-to-year... possibly much higher. In the end, this discussion is moot without any hard figures. If Soto wanted to sell his next 5 seasons for $10M, then you have to take it. But if I'm running the team, unless I'm getting a real sweetheart deal like that, I'm keeping my options open and going year-to-year. If the guy blows up and winds up costing me more than I could've gotten him for, then that's a nice problem to have. What's not a nice problem to have is having $6 or $8M a year committed for another 2-3 years on the next Rocco Baldelli... or Mark Prior for that matter. Just imagine how much worse that Prior situation would've been if he was making Tulowitzki money. You can't really compare pitchers to position players. Pitchers have a much higher injury rate and are thus a much bigger risk. Is it your opinion that all of these pre-FA extensions have been bad moves? Because Berroa is the only one I can think of that hasn't turned out well thus far.