Success usually comes at a cost, and that's certainly the case for the 2023-24 Boston Celtics.

Due to the new CBA rules, keeping multiple star players requires financial finesse. It helps that the C's drafted stars Jayson Tatum and Jaylen Brown several years ago, yet they'll still likely land in the second luxury tax apron for the 2024-25 season, facing salary-matching restrictions and other monetary obstacles.

However, Boston is willing to pay what it must for wins. That plan of attack has worked out well so far, as the Celtics are currently up 2-0 on the Dallas Mavericks in the 2024 NBA Finals. To get to this point, the front office had to pay franchise cornerstones and bring some new ones in recently.

Two-way guard Derrick White has elevated his game to become one of those essential pieces on Boston's roster. The 29-year-old was dealt to the Celtics in February of 2022 and has only flourished since.

During the 2023-24 regular season, White averaged 15.2 points, 5.2 assists, 4.2 rebounds and 1.2 blocks per game. He also shot 39.6% from deep, which was his best conversion rate since his rookie season seven years ago (and he only played in 17 games that year).

The Colorado native has become a fan favorite in Beantown, and it sounds like he'd like to stay with the Celtics long-term if possible.

“White, according to league sources, will be seeking a contract extension this summer,” NBA insider Marc Stein reports.

Given that White dazzled in the regular season and then dropped a career-high 38 points in Game 4 of the first round of the playoffs versus the Miami Heat, he should be in for a hefty payday.

Why Celtics' spending emphasizes win-now importance

Boston Celtics majority owner Wyc Grousbeck watches from the sideline as his team takes on the Brooklyn Nets at TD Garden
David Butler II-USA TODAY Sports

This past offseason, Brown made waves by inking the richest contract in league history, taking in nearly $290 million via a supermax extension. Meanwhile, Tatum could have a similar deal lined up this summer. The 26-year-old is eligible for a five-year extension worth up to $315 million starting in July. If that number is met, the Celtics will have back-to-back offseasons with record-breaking extensions.

On top of that, veteran guard Jrue Holiday just got an extension as well. Right before the 2024 postseason began, Holiday agreed to a four-year, $135 million deal. Getting this paperwork done ahead of the playoffs has allowed the 34-year-old to focus purely on basketball, as he led the C's in scoring during Game 2 of the Finals with 26 points (11-for-14 from the field).

“He took the role on this new team and developed into almost a new player,” Brown said of Holiday during a Tuesday afternoon press conference. “I don't overlook stuff like that. I think those are forms of greatness. Even though we expect greatness to be these things that are so large or so captivating. Stuff like that doesn't go unnoticed to guys like me. It's been an honor to be his teammate.”

Will all this spent money leave room for White? It might be tough to maneuver, but Boston's front office has shown a willingness to throw around major moolah when required. Celtics majority owner Wyc Grousbeck made that clear when asked about his spending strategies.

“We will be paid in enjoyment,” he said, per the Boston Globe. “We will be paid in parades.”

The Celtics are just two wins away from delivering on that promise. Now is the best time to do it, too, because there's no guarantee their championship window will stay open forever, especially with the confining CBA, growing tax penalties and need to pay plenty of talented players what they deserve.

Despite the 2-0 cushion, the Celtics know there's still a lot of work to be done if they want bring banner No. 18 to TD Garden.

“You almost got to play like you're down 0-2 rather than up,” Brown stated. “That's hard to do. You got to go into that mind frame, that focus. Now we are playing like that, rather than you let comfort, you let some of those things kind of seep in. You just try to stay focused and try to harness the mind as much as you can.”

After protecting home court, the Celtics are now in Dallas for Game 3, which tips off on Wednesday night at the American Airlines Center.